As useful as they are, soaps also have drawbacks. In hard water, which contains metal ions, soluble sodium carboxylates are converted into insoluble magnesium and calcium salts, leaving the familiar ring of scum around bathtubs and a gray tinge on white clothes. Chemists have circumvented this problem by synthesizing a class of synthetic detergents based on salts of long-chain alkylbenzenesulfonic acids. The mechanism of synthetic detergents is the same as that of soaps: the alkylbenzene end of the molecule is attracted to grease, while the anionic sulfonate end is attracted to water. Unlike soaps, though, sulfonate detergents don't form insoluble metal salts in hard water and don't leave an unpleasant scum.
<img class="imgSvg" id = "m6sn3px5vesobr424hk" src="data:image/svg+xml;base64,<svg id="smiles-m6sn3px5vesobr424hk" xmlns="http://www.w3.org/2000/svg" viewBox="0 0 241 104.99999999997463" style="width: 241.4999999999365px; height: 104.99999999997463px; overflow: visible;"><defs><linearGradient id="line-m6sn3px5vesobr424hk-1" gradientUnits="userSpaceOnUse" x1="167.99999999994924" y1="52.500084823830335" x2="199.4999999999365" y2="52.5001130984447"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3px5vesobr424hk-3" gradientUnits="userSpaceOnUse" x1="148.9146164673336" y1="74.21688788995776" x2="161.51463605655596" y2="52.39305902444447"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3px5vesobr424hk-5" gradientUnits="userSpaceOnUse" x1="152.2499755134213" y1="79.77987090572198" x2="167.99999999994924" y2="52.500084823830335"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3px5vesobr424hk-7" gradientUnits="userSpaceOnUse" x1="152.25002448648985" y1="25.220270467324312" x2="167.99999999994924" y2="52.500084823830335"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3px5vesobr424hk-9" gradientUnits="userSpaceOnUse" x1="120.749975513434" y1="79.77984263110766" x2="152.2499755134213" y2="79.77987090572198"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3px5vesobr424hk-11" gradientUnits="userSpaceOnUse" x1="123.9000193970707" y1="30.890245020169132" x2="149.10001939706058" y2="30.890267639860596"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3px5vesobr424hk-13" gradientUnits="userSpaceOnUse" x1="120.75002448650254" y1="25.22024219270999" x2="152.25002448648985" y2="25.220270467324312"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3px5vesobr424hk-15" gradientUnits="userSpaceOnUse" x1="111.48536413549162" y1="52.39301411782955" x2="124.08534454625912" y2="74.21686560303435"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3px5vesobr424hk-17" gradientUnits="userSpaceOnUse" x1="104.9999999999746" y1="52.50002827460165" x2="120.749975513434" y2="79.77984263110766"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3px5vesobr424hk-19" gradientUnits="userSpaceOnUse" x1="104.9999999999746" y1="52.50002827460165" x2="120.75002448650254" y2="25.22024219270999"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3px5vesobr424hk-21" gradientUnits="userSpaceOnUse" x1="73.49999999998731" y1="52.49999999998731" x2="104.9999999999746" y2="52.50002827460165"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3px5vesobr424hk-23" gradientUnits="userSpaceOnUse" x1="42.00000254471529" y1="49.66497172537413" x2="73.5000025447026" y2="49.66499999998845"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3px5vesobr424hk-25" gradientUnits="userSpaceOnUse" x1="41.99999745528471" y1="55.334971725371844" x2="73.49999745527202" y2="55.33499999998617"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3px5vesobr424hk-27" gradientUnits="userSpaceOnUse" x1="76.33499999998618" y1="52.500002544702596" x2="76.3350282746005" y2="21.000002544715286"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3px5vesobr424hk-29" gradientUnits="userSpaceOnUse" x1="70.66499999998845" y1="52.49999745527202" x2="70.66502827460278" y2="20.999997455284714"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3px5vesobr424hk-31" gradientUnits="userSpaceOnUse" x1="73.49997172537297" y1="83.99999999997463" x2="73.49999999998731" y2="52.49999999998731"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient></defs><mask id="text-mask-m6sn3px5vesobr424hk"><rect x="0" y="0" width="100%" height="100%" fill="white"></rect><circle cx="199.4999999999365" cy="52.5001130984447" r="7.875" fill="black"></circle><circle cx="73.49999999998731" cy="52.49999999998731" r="7.875" fill="black"></circle><circle cx="42" cy="52.49997172537299" r="7.875" fill="black"></circle><circle cx="73.50002827460163" cy="21" r="7.875" fill="black"></circle><circle cx="73.49997172537297" cy="83.99999999997463" r="7.875" fill="black"></circle></mask><style>
                .element-m6sn3px5vesobr424hk {
                    font: 14px Helvetica, Arial, sans-serif;
                    alignment-baseline: 'middle';
                }
                .sub-m6sn3px5vesobr424hk {
                    font: 8.4px Helvetica, Arial, sans-serif;
                }
            </style><g mask="url(#text-mask-m6sn3px5vesobr424hk)"><line x1="167.99999999994924" y1="52.500084823830335" x2="199.4999999999365" y2="52.5001130984447" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-1')"></line><line x1="148.9146164673336" y1="74.21688788995776" x2="161.51463605655596" y2="52.39305902444447" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-3')"></line><line x1="152.2499755134213" y1="79.77987090572198" x2="167.99999999994924" y2="52.500084823830335" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-5')"></line><line x1="152.25002448648985" y1="25.220270467324312" x2="167.99999999994924" y2="52.500084823830335" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-7')"></line><line x1="120.749975513434" y1="79.77984263110766" x2="152.2499755134213" y2="79.77987090572198" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-9')"></line><line x1="123.9000193970707" y1="30.890245020169132" x2="149.10001939706058" y2="30.890267639860596" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-11')"></line><line x1="120.75002448650254" y1="25.22024219270999" x2="152.25002448648985" y2="25.220270467324312" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-13')"></line><line x1="111.48536413549162" y1="52.39301411782955" x2="124.08534454625912" y2="74.21686560303435" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-15')"></line><line x1="104.9999999999746" y1="52.50002827460165" x2="120.749975513434" y2="79.77984263110766" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-17')"></line><line x1="104.9999999999746" y1="52.50002827460165" x2="120.75002448650254" y2="25.22024219270999" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-19')"></line><line x1="73.49999999998731" y1="52.49999999998731" x2="104.9999999999746" y2="52.50002827460165" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-21')"></line><line x1="42.00000254471529" y1="49.66497172537413" x2="73.5000025447026" y2="49.66499999998845" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-23')"></line><line x1="41.99999745528471" y1="55.334971725371844" x2="73.49999745527202" y2="55.33499999998617" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-25')"></line><line x1="76.33499999998618" y1="52.500002544702596" x2="76.3350282746005" y2="21.000002544715286" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-27')"></line><line x1="70.66499999998845" y1="52.49999745527202" x2="70.66502827460278" y2="20.999997455284714" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-29')"></line><line x1="73.49997172537297" y1="83.99999999997463" x2="73.49999999998731" y2="52.49999999998731" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3px5vesobr424hk-31')"></line></g><g><text x="195.5624999999365" y="57.7501130984447" class="element-m6sn3px5vesobr424hk" fill="currentColor" style="
                text-anchor: start;
                writing-mode: horizontal-tb;
                text-orientation: mixed;
                letter-spacing: normal;
                direction: ltr;
            "><tspan>R</tspan></text><text x="199.4999999999365" y="52.5001130984447" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="167.99999999994924" y="52.500084823830335" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="152.2499755134213" y="79.77987090572198" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="120.749975513434" y="79.77984263110766" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="104.9999999999746" y="52.50002827460165" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="73.49999999998731" y="60.37499999998731" class="element-m6sn3px5vesobr424hk" fill="currentColor" style="
                text-anchor: start;
                writing-mode: vertical-rl;
                text-orientation: upright;
                letter-spacing: -1px;
                direction: rtl; unicode-bidi: bidi-override;
            "><tspan>S</tspan></text><text x="73.49999999998731" y="52.49999999998731" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="47.25" y="57.74997172537299" class="element-m6sn3px5vesobr424hk" fill="currentColor" style="
                text-anchor: start;
                writing-mode: horizontal-tb;
                text-orientation: mixed;
                letter-spacing: normal;
                direction: rtl; unicode-bidi: bidi-override;
            "><tspan>O</tspan></text><text x="42" y="52.49997172537299" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="68.25002827460163" y="26.25" class="element-m6sn3px5vesobr424hk" fill="currentColor" style="
                text-anchor: start;
                writing-mode: horizontal-tb;
                text-orientation: mixed;
                letter-spacing: normal;
                direction: ltr;
            "><tspan>O</tspan></text><text x="73.50002827460163" y="21" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="68.24997172537297" y="89.24999999997463" class="element-m6sn3px5vesobr424hk" fill="currentColor" style="
                text-anchor: start;
                writing-mode: horizontal-tb;
                text-orientation: mixed;
                letter-spacing: normal;
                direction: ltr;
            "><tspan>O<tspan baseline-shift="super" class="sub-m6sn3px5vesobr424hk">-</tspan></tspan></text><text x="73.49997172537297" y="83.99999999997463" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="120.75002448650254" y="25.22024219270999" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="152.25002448648985" y="25.220270467324312" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text></g></svg>"/>


A fat ( $\mathrm{R}=\mathrm{C}_{11}-\mathrm{C}_{19}$ Aliphatic chains) -

A synthetic detergent
( $R=$ various $C_{12}$ chains)
PROBLEM Draw the structure of magnesium oleate, a component of bathtub scum.
27-3
PROBLEM Write the saponification reaction of glyceryl dioleate monopalmitate with aqueous NaOH .
27-4


A fat ( $\mathrm{R}=\mathrm{C}_{11}-\mathrm{C}_{19}$ Aliphatic chains) - 27.3 Phospholipids


A phosphoric acid triester


Phospholipids are of two general types: glycerophospholipids and sphingomyelins. Glycerophospholipids are based on phosphatidic acid, which contains a glycerol backbone linked by ester bonds to two fatty acids and one phosphoric acid. Although the fatty-acid residues can be any of the $\mathrm{C}_{12}-\mathrm{C}_{20}$ units typically present in fats, the acyl group at C 1 is usually saturated and the one at C 2 is usually unsaturated. The phosphate group at C 3 is also
bonded to an amino alcohol such as choline $\left[\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{~N}\left(\mathrm{CH}_{3}\right)_{3}\right]^{+}$, ethanolamine $\left(\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\right)$, or serine $\left[\mathrm{HOCH}_{2} \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{CO}_{2} \mathrm{H}\right]$. The compounds are chiral and have an L , or $R$, configuration at C 2 .
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0983.jpg?height=849&width=1464&top_left_y=302&top_left_x=325)


Sphingomyelins are the second major group of phospholipids. These compounds have sphingosine or a related dihydroxyamine as their backbone and are particularly abundant in brain and nerve tissue, where they are a major constituent of the coating around nerve fibers.
<img class="imgSvg" id = "m6sn3pxnptco42rtv5m" src="data:image/svg+xml;base64,<svg id="smiles-m6sn3pxnptco42rtv5m" xmlns="http://www.w3.org/2000/svg" viewBox="0 0 439 120.75001836488292" style="width: 438.6373922466668px; height: 120.75001836488292px; overflow: visible;"><defs><linearGradient id="line-m6sn3pxnptco42rtv5m-1" gradientUnits="userSpaceOnUse" x1="369.35760263044364" y1="52.50018364900029" x2="396.6373922466668" y2="68.25020201389742"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pxnptco42rtv5m-3" gradientUnits="userSpaceOnUse" x1="342.0777918082596" y1="68.25016528409594" x2="369.35760263044364" y2="52.50018364900029"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pxnptco42rtv5m-5" gradientUnits="userSpaceOnUse" x1="314.79800219203634" y1="52.50014691919881" x2="342.0777918082596" y2="68.25016528409594"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pxnptco42rtv5m-7" gradientUnits="userSpaceOnUse" x1="287.51819136985233" y1="68.25012855429446" x2="314.79800219203634" y2="52.50014691919881"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pxnptco42rtv5m-9" gradientUnits="userSpaceOnUse" x1="260.23840175362903" y1="52.50011018939733" x2="287.51819136985233" y2="68.25012855429446"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pxnptco42rtv5m-11" gradientUnits="userSpaceOnUse" x1="232.95859093144506" y1="68.25009182449298" x2="260.23840175362903" y2="52.50011018939733"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pxnptco42rtv5m-13" gradientUnits="userSpaceOnUse" x1="205.6788013152218" y1="52.50007345959585" x2="232.95859093144506" y2="68.25009182449298"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pxnptco42rtv5m-15" gradientUnits="userSpaceOnUse" x1="178.3989904930378" y1="68.2500550946915" x2="205.6788013152218" y2="52.50007345959585"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pxnptco42rtv5m-17" gradientUnits="userSpaceOnUse" x1="151.11920087681452" y1="52.500036729794374" x2="178.3989904930378" y2="68.2500550946915"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pxnptco42rtv5m-19" gradientUnits="userSpaceOnUse" x1="123.8393900546305" y1="68.25001836489002" x2="151.11920087681452" y2="52.500036729794374"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pxnptco42rtv5m-21" gradientUnits="userSpaceOnUse" x1="123.83936884866974" y1="99.75001836488292" x2="123.8393900546305" y2="68.25001836489002"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pxnptco42rtv5m-23" gradientUnits="userSpaceOnUse" x1="96.55960043840727" y1="52.499999999992895" x2="123.8393900546305" y2="68.25001836489002"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pxnptco42rtv5m-25" gradientUnits="userSpaceOnUse" x1="96.55960043840727" y1="52.499999999992895" x2="96.55962164436804" y2="21"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pxnptco42rtv5m-27" gradientUnits="userSpaceOnUse" x1="69.27978961622323" y1="68.24998163508855" x2="96.55960043840727" y2="52.499999999992895"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pxnptco42rtv5m-29" gradientUnits="userSpaceOnUse" x1="42" y1="52.49996327019136" x2="69.27978961622323" y2="68.24998163508855"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient></defs><mask id="text-mask-m6sn3pxnptco42rtv5m"><rect x="0" y="0" width="100%" height="100%" fill="white"></rect><circle cx="123.83936884866974" cy="99.75001836488292" r="7.875" fill="black"></circle><circle cx="96.55962164436804" cy="21" r="7.875" fill="black"></circle><circle cx="42" cy="52.49996327019136" r="7.875" fill="black"></circle></mask><style>
                .element-m6sn3pxnptco42rtv5m {
                    font: 14px Helvetica, Arial, sans-serif;
                    alignment-baseline: 'middle';
                }
                .sub-m6sn3pxnptco42rtv5m {
                    font: 8.4px Helvetica, Arial, sans-serif;
                }
            </style><g mask="url(#text-mask-m6sn3pxnptco42rtv5m)"><line x1="369.35760263044364" y1="52.50018364900029" x2="396.6373922466668" y2="68.25020201389742" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pxnptco42rtv5m-1')"></line><line x1="342.0777918082596" y1="68.25016528409594" x2="369.35760263044364" y2="52.50018364900029" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pxnptco42rtv5m-3')"></line><line x1="314.79800219203634" y1="52.50014691919881" x2="342.0777918082596" y2="68.25016528409594" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pxnptco42rtv5m-5')"></line><line x1="287.51819136985233" y1="68.25012855429446" x2="314.79800219203634" y2="52.50014691919881" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pxnptco42rtv5m-7')"></line><line x1="260.23840175362903" y1="52.50011018939733" x2="287.51819136985233" y2="68.25012855429446" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pxnptco42rtv5m-9')"></line><line x1="232.95859093144506" y1="68.25009182449298" x2="260.23840175362903" y2="52.50011018939733" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pxnptco42rtv5m-11')"></line><line x1="205.6788013152218" y1="52.50007345959585" x2="232.95859093144506" y2="68.25009182449298" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pxnptco42rtv5m-13')"></line><line x1="178.3989904930378" y1="68.2500550946915" x2="205.6788013152218" y2="52.50007345959585" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pxnptco42rtv5m-15')"></line><line x1="151.11920087681452" y1="52.500036729794374" x2="178.3989904930378" y2="68.2500550946915" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pxnptco42rtv5m-17')"></line><line x1="123.8393900546305" y1="68.25001836489002" x2="151.11920087681452" y2="52.500036729794374" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pxnptco42rtv5m-19')"></line><line x1="123.83936884866974" y1="99.75001836488292" x2="123.8393900546305" y2="68.25001836489002" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pxnptco42rtv5m-21')"></line><line x1="96.55960043840727" y1="52.499999999992895" x2="123.8393900546305" y2="68.25001836489002" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pxnptco42rtv5m-23')"></line><line x1="96.55960043840727" y1="52.499999999992895" x2="96.55962164436804" y2="21" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pxnptco42rtv5m-25')"></line><line x1="69.27978961622323" y1="68.24998163508855" x2="96.55960043840727" y2="52.499999999992895" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pxnptco42rtv5m-27')"></line><line x1="42" y1="52.49996327019136" x2="69.27978961622323" y2="68.24998163508855" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pxnptco42rtv5m-29')"></line></g><g><text x="396.6373922466668" y="68.25020201389742" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="369.35760263044364" y="52.50018364900029" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="342.0777918082596" y="68.25016528409594" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="314.79800219203634" y="52.50014691919881" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="287.51819136985233" y="68.25012855429446" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="260.23840175362903" y="52.50011018939733" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="232.95859093144506" y="68.25009182449298" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="205.6788013152218" y="52.50007345959585" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="178.3989904930378" y="68.2500550946915" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="151.11920087681452" y="52.500036729794374" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="123.8393900546305" y="68.25001836489002" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="118.58936884866974" y="105.00001836488292" class="element-m6sn3pxnptco42rtv5m" fill="currentColor" style="
                text-anchor: start;
                writing-mode: horizontal-tb;
                text-orientation: mixed;
                letter-spacing: normal;
                direction: ltr;
            "><tspan>N</tspan><tspan style="unicode-bidi: plaintext;">H<tspan baseline-shift="sub" class="sub-m6sn3pxnptco42rtv5m">2</tspan></tspan></text><text x="123.83936884866974" y="99.75001836488292" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="96.55960043840727" y="52.499999999992895" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="91.30962164436804" y="26.25" class="element-m6sn3pxnptco42rtv5m" fill="currentColor" style="
                text-anchor: start;
                writing-mode: horizontal-tb;
                text-orientation: mixed;
                letter-spacing: normal;
                direction: ltr;
            "><tspan>O</tspan><tspan style="unicode-bidi: plaintext;">H</tspan></text><text x="96.55962164436804" y="21" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="69.27978961622323" y="68.24998163508855" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="47.25" y="57.74996327019136" class="element-m6sn3pxnptco42rtv5m" fill="currentColor" style="
                text-anchor: start;
                writing-mode: horizontal-tb;
                text-orientation: mixed;
                letter-spacing: normal;
                direction: rtl; unicode-bidi: bidi-override;
            "><tspan>O</tspan><tspan style="unicode-bidi: plaintext;">H</tspan></text><text x="42" y="52.49996327019136" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text></g></svg>"/>


Sphingosine
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0983.jpg?height=264&width=768&top_left_y=1299&top_left_x=955)


A sphingomyelin


Phospholipids are found widely in both plant and animal tissues and make up approximately $50 \%$ to $60 \%$ of cell membranes. Because they are like soaps in having a long, nonpolar hydrocarbon tail bound to a polar ionic head, phospholipids in the cell membrane organize into a lipid bilayer about $5.0 \mathrm{~nm}(50 \AA$ ) thick. As shown in FIGURE 27.3, the nonpolar tails aggregate in the center of the bilayer in much the same way that soap tails aggregate in the center of a micelle. This bilayer serves as an effective barrier to the passage of water, ions, and other components into and out of cells.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0983.jpg?height=261&width=467&top_left_y=2016&top_left_x=428)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0983.jpg?height=386&width=772&top_left_y=1921&top_left_x=926)


FIGURE 27.3 Aggregation of glycerophospholipids into the lipid bilayer that composes cell membranes.


A fat ( $\mathrm{R}=\mathrm{C}_{11}-\mathrm{C}_{19}$ Aliphatic chains) - 27.4 Prostaglandins and Other Eicosanoids

Prostaglandins are a group of $\mathrm{C}_{20}$ lipids that contain a five-membered ring with two long side chains. First isolated in the 1930s by Ulf von Euler at the Karolinska Institute in Sweden, much of the structural and chemical
work on prostaglandins was carried out by Sune Bergström and Bengt Samuelsson. All three shared Nobel Prizes for their work. The name prostaglandin derives from the fact that the compounds were first isolated from sheep prostate glands, but they have subsequently been found to be present in small amounts in all body tissues and fluids.


The several dozen known prostaglandins have an extraordinarily wide range of biological effects. Among their many properties, they can lower blood pressure, affect blood platelet aggregation during clotting, lower gastric secretions, control inflammation, affect kidney function, affect reproductive systems, and stimulate uterine contractions during childbirth.


Prostaglandins, together with related compounds called thromboxanes and leukotrienes, make up a class of compounds called eicosanoids because they are derived biologically from 5,8,11,14-eicosatetraenoic acid, or arachidonic acid (FIGURE 27.4). Prostaglandins (PG) have a cyclopentane ring with two long side chains; thromboxanes (TX) have a six-membered, oxygen-containing ring; and leukotrienes (LT) are acyclic.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0984.jpg?height=212&width=511&top_left_y=783&top_left_x=425)


Leukotriene $\mathrm{E}_{\mathbf{4}}\left(\mathrm{LTE}_{4}\right)$


FIGURE 27.4 Structures of some representative eicosanoids. All are derived biologically from arachidonic acid.
Eicosanoids are named based on their ring system (PG, TX, or LT), substitution pattern, and number of double bonds. The various substitution patterns on the ring are indicated by letter as in FIGURE 27.5, and the number of double bonds is indicated by a subscript. Thus, $\mathrm{PGE}_{1}$ is a prostaglandin with the "E" substitution pattern and one double bond. The numbering of the atoms in the various eicosanoids is the same as in arachidonic acid, starting with the $-\mathrm{CO}_{2} \mathrm{H}$ carbon as C 1 , continuing around the ring, and ending with the $-\mathrm{CH}_{3}$ carbon at the other end of the chain as C20.
<img class="imgSvg" id = "m6sn3pyedgrk64hpmcf" src="data:image/svg+xml;base64,<svg id="smiles-m6sn3pyedgrk64hpmcf" xmlns="http://www.w3.org/2000/svg" viewBox="0 0 164 122.92634217155009" style="width: 163.9735298477852px; height: 122.92634217155009px; overflow: visible;"><defs><linearGradient id="line-m6sn3pyedgrk64hpmcf-1" gradientUnits="userSpaceOnUse" x1="90.47352984779789" y1="76.44232346815085" x2="121.97352984778519" y2="76.44235174276523"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyedgrk64hpmcf-3" gradientUnits="userSpaceOnUse" x1="71.95827152594893" y1="101.92634217155009" x2="90.47352984779789" y2="76.44232346815085"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyedgrk64hpmcf-5" gradientUnits="userSpaceOnUse" x1="71.95831727523594" y1="50.95827152594894" x2="90.47352984779789" y2="76.44232346815085"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyedgrk64hpmcf-7" gradientUnits="userSpaceOnUse" x1="42" y1="92.19227995798695" x2="71.95827152594893" y2="101.92634217155009"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyedgrk64hpmcf-9" gradientUnits="userSpaceOnUse" x1="42.00002827461434" y1="60.69227995799965" x2="71.95831727523594" y2="50.95827152594894"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyedgrk64hpmcf-11" gradientUnits="userSpaceOnUse" x1="71.95831727523594" y1="50.95827152594894" x2="81.69237948879908" y2="21"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyedgrk64hpmcf-13" gradientUnits="userSpaceOnUse" x1="42" y1="92.19227995798695" x2="42.00002827461434" y2="60.69227995799965"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient></defs><mask id="text-mask-m6sn3pyedgrk64hpmcf"><rect x="0" y="0" width="100%" height="100%" fill="white"></rect><circle cx="121.97352984778519" cy="76.44235174276523" r="7.875" fill="black"></circle><circle cx="81.69237948879908" cy="21" r="7.875" fill="black"></circle></mask><style>
                .element-m6sn3pyedgrk64hpmcf {
                    font: 14px Helvetica, Arial, sans-serif;
                    alignment-baseline: 'middle';
                }
                .sub-m6sn3pyedgrk64hpmcf {
                    font: 8.4px Helvetica, Arial, sans-serif;
                }
            </style><g mask="url(#text-mask-m6sn3pyedgrk64hpmcf)"><line x1="90.47352984779789" y1="76.44232346815085" x2="121.97352984778519" y2="76.44235174276523" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyedgrk64hpmcf-1')"></line><line x1="71.95827152594893" y1="101.92634217155009" x2="90.47352984779789" y2="76.44232346815085" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyedgrk64hpmcf-3')"></line><line x1="71.95831727523594" y1="50.95827152594894" x2="90.47352984779789" y2="76.44232346815085" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyedgrk64hpmcf-5')"></line><line x1="42" y1="92.19227995798695" x2="71.95827152594893" y2="101.92634217155009" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyedgrk64hpmcf-7')"></line><line x1="42.00002827461434" y1="60.69227995799965" x2="71.95831727523594" y2="50.95827152594894" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyedgrk64hpmcf-9')"></line><line x1="71.95831727523594" y1="50.95827152594894" x2="81.69237948879908" y2="21" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyedgrk64hpmcf-11')"></line><line x1="42" y1="92.19227995798695" x2="42.00002827461434" y2="60.69227995799965" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyedgrk64hpmcf-13')"></line></g><g><text x="118.03602984778519" y="81.69235174276523" class="element-m6sn3pyedgrk64hpmcf" fill="currentColor" style="
                text-anchor: start;
                writing-mode: horizontal-tb;
                text-orientation: mixed;
                letter-spacing: normal;
                direction: ltr;
            "><tspan>R</tspan></text><text x="121.97352984778519" y="76.44235174276523" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="90.47352984779789" y="76.44232346815085" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="71.95827152594893" y="101.92634217155009" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="42" y="92.19227995798695" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="42.00002827461434" y="60.69227995799965" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="71.95831727523594" y="50.95827152594894" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="76.44237948879908" y="26.25" class="element-m6sn3pyedgrk64hpmcf" fill="currentColor" style="
                text-anchor: start;
                writing-mode: horizontal-tb;
                text-orientation: mixed;
                letter-spacing: normal;
                direction: ltr;
            "><tspan>R</tspan></text><text x="81.69237948879908" y="21" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text></g></svg>"/>

A prostaglandin (PG)
<img class="imgSvg" id = "m6sn3pyfj2dra9krgwc" src="data:image/svg+xml;base64,<svg id="smiles-m6sn3pyfj2dra9krgwc" xmlns="http://www.w3.org/2000/svg" viewBox="0 0 178 123.83938652028935" style="width: 178.49999999996197px; height: 123.83938652028935px; overflow: visible;"><defs><linearGradient id="line-m6sn3pyfj2dra9krgwc-1" gradientUnits="userSpaceOnUse" x1="104.99999999997463" y1="75.55960043839771" x2="136.49999999996197" y2="75.55962871301207"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyfj2dra9krgwc-3" gradientUnits="userSpaceOnUse" x1="89.24997551344667" y1="102.83938652028935" x2="104.99999999997463" y2="75.55960043839771"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyfj2dra9krgwc-5" gradientUnits="userSpaceOnUse" x1="89.25002448651524" y1="48.279786081891686" x2="104.99999999997463" y2="75.55960043839771"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyfj2dra9krgwc-7" gradientUnits="userSpaceOnUse" x1="57.74997551345936" y1="102.83935824567502" x2="89.24997551344667" y2="102.83938652028935"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyfj2dra9krgwc-9" gradientUnits="userSpaceOnUse" x1="57.75002448652795" y1="48.27975780727736" x2="89.25002448651524" y2="48.279786081891686"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyfj2dra9krgwc-11" gradientUnits="userSpaceOnUse" x1="89.25002448651524" y1="48.279786081891686" x2="105.00004897304316" y2="21"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyfj2dra9krgwc-13" gradientUnits="userSpaceOnUse" x1="42" y1="75.55954388916902" x2="57.74997551345936" y2="102.83935824567502"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyfj2dra9krgwc-15" gradientUnits="userSpaceOnUse" x1="42" y1="75.55954388916902" x2="57.75002448652795" y2="48.27975780727736"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient></defs><mask id="text-mask-m6sn3pyfj2dra9krgwc"><rect x="0" y="0" width="100%" height="100%" fill="white"></rect><circle cx="136.49999999996197" cy="75.55962871301207" r="7.875" fill="black"></circle><circle cx="57.75002448652795" cy="48.27975780727736" r="7.875" fill="black"></circle><circle cx="105.00004897304316" cy="21" r="7.875" fill="black"></circle></mask><style>
                .element-m6sn3pyfj2dra9krgwc {
                    font: 14px Helvetica, Arial, sans-serif;
                    alignment-baseline: 'middle';
                }
                .sub-m6sn3pyfj2dra9krgwc {
                    font: 8.4px Helvetica, Arial, sans-serif;
                }
            </style><g mask="url(#text-mask-m6sn3pyfj2dra9krgwc)"><line x1="104.99999999997463" y1="75.55960043839771" x2="136.49999999996197" y2="75.55962871301207" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyfj2dra9krgwc-1')"></line><line x1="89.24997551344667" y1="102.83938652028935" x2="104.99999999997463" y2="75.55960043839771" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyfj2dra9krgwc-3')"></line><line x1="89.25002448651524" y1="48.279786081891686" x2="104.99999999997463" y2="75.55960043839771" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyfj2dra9krgwc-5')"></line><line x1="57.74997551345936" y1="102.83935824567502" x2="89.24997551344667" y2="102.83938652028935" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyfj2dra9krgwc-7')"></line><line x1="57.75002448652795" y1="48.27975780727736" x2="89.25002448651524" y2="48.279786081891686" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyfj2dra9krgwc-9')"></line><line x1="89.25002448651524" y1="48.279786081891686" x2="105.00004897304316" y2="21" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyfj2dra9krgwc-11')"></line><line x1="42" y1="75.55954388916902" x2="57.74997551345936" y2="102.83935824567502" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyfj2dra9krgwc-13')"></line><line x1="42" y1="75.55954388916902" x2="57.75002448652795" y2="48.27975780727736" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyfj2dra9krgwc-15')"></line></g><g><text x="132.56249999996197" y="80.80962871301207" class="element-m6sn3pyfj2dra9krgwc" fill="currentColor" style="
                text-anchor: start;
                writing-mode: horizontal-tb;
                text-orientation: mixed;
                letter-spacing: normal;
                direction: ltr;
            "><tspan>R</tspan></text><text x="136.49999999996197" y="75.55962871301207" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="104.99999999997463" y="75.55960043839771" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="89.24997551344667" y="102.83938652028935" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="57.74997551345936" y="102.83935824567502" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="42" y="75.55954388916902" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="57.75002448652795" y="56.15475780727736" class="element-m6sn3pyfj2dra9krgwc" fill="currentColor" style="
                text-anchor: start;
                writing-mode: vertical-rl;
                text-orientation: upright;
                letter-spacing: -1px;
                direction: rtl; unicode-bidi: bidi-override;
            "><tspan>O</tspan></text><text x="57.75002448652795" y="48.27975780727736" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="89.25002448651524" y="48.279786081891686" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="99.75004897304316" y="26.25" class="element-m6sn3pyfj2dra9krgwc" fill="currentColor" style="
                text-anchor: start;
                writing-mode: horizontal-tb;
                text-orientation: mixed;
                letter-spacing: normal;
                direction: ltr;
            "><tspan>R</tspan></text><text x="105.00004897304316" y="21" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text></g></svg>"/>

A thromboxane (TX)
<img class="imgSvg" id = "m6sn3pyt8wsti4vp15s" src="data:image/svg+xml;base64,<svg id="smiles-m6sn3pyt8wsti4vp15s" xmlns="http://www.w3.org/2000/svg" viewBox="0 0 248 105.00002448653274" style="width: 247.67880131525487px; height: 105.00002448653274px; overflow: visible;"><defs><linearGradient id="line-m6sn3pyt8wsti4vp15s-1" gradientUnits="userSpaceOnUse" x1="178.3989975617189" y1="36.75003060816749" x2="205.67880131525487" y2="21.00003672980148"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyt8wsti4vp15s-3" gradientUnits="userSpaceOnUse" x1="178.3989904930653" y1="68.2500306081667" x2="178.3989975617189" y2="36.75003060816749"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyt8wsti4vp15s-5" gradientUnits="userSpaceOnUse" x1="156.68216601298886" y1="87.33538977433258" x2="178.5060090158176" y2="74.73539467163977"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyt8wsti4vp15s-7" gradientUnits="userSpaceOnUse" x1="151.11918673952937" y1="84.00002448653274" x2="178.3989904930653" y2="68.2500306081667"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyt8wsti4vp15s-9" gradientUnits="userSpaceOnUse" x1="123.83939005464704" y1="68.25001836489955" x2="151.11918673952937" y2="84.00002448653274"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyt8wsti4vp15s-11" gradientUnits="userSpaceOnUse" x1="96.55958630111111" y1="84.00001224326556" x2="123.83939005464704" y2="68.25001836489955"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyt8wsti4vp15s-13" gradientUnits="userSpaceOnUse" x1="69.17276818282303" y1="74.73537013707451" x2="90.99660553072891" y2="87.33537503438109"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyt8wsti4vp15s-15" gradientUnits="userSpaceOnUse" x1="69.27978961622877" y1="68.2500061216324" x2="96.55958630111111" y2="84.00001224326556"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyt8wsti4vp15s-17" gradientUnits="userSpaceOnUse" x1="69.27978961622877" y1="68.2500061216324" x2="69.27979668488234" y2="36.75000612163318"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient><linearGradient id="line-m6sn3pyt8wsti4vp15s-19" gradientUnits="userSpaceOnUse" x1="42.000000000000014" y1="21" x2="69.27979668488234" y2="36.75000612163318"><stop stop-color="currentColor" offset="20%"></stop><stop stop-color="currentColor" offset="100%"></stop></linearGradient></defs><mask id="text-mask-m6sn3pyt8wsti4vp15s"><rect x="0" y="0" width="100%" height="100%" fill="white"></rect><circle cx="205.67880131525487" cy="21.00003672980148" r="7.875" fill="black"></circle><circle cx="42.000000000000014" cy="21" r="7.875" fill="black"></circle></mask><style>
                .element-m6sn3pyt8wsti4vp15s {
                    font: 14px Helvetica, Arial, sans-serif;
                    alignment-baseline: 'middle';
                }
                .sub-m6sn3pyt8wsti4vp15s {
                    font: 8.4px Helvetica, Arial, sans-serif;
                }
            </style><g mask="url(#text-mask-m6sn3pyt8wsti4vp15s)"><line x1="178.3989975617189" y1="36.75003060816749" x2="205.67880131525487" y2="21.00003672980148" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyt8wsti4vp15s-1')"></line><line x1="178.3989904930653" y1="68.2500306081667" x2="178.3989975617189" y2="36.75003060816749" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyt8wsti4vp15s-3')"></line><line x1="156.68216601298886" y1="87.33538977433258" x2="178.5060090158176" y2="74.73539467163977" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyt8wsti4vp15s-5')"></line><line x1="151.11918673952937" y1="84.00002448653274" x2="178.3989904930653" y2="68.2500306081667" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyt8wsti4vp15s-7')"></line><line x1="123.83939005464704" y1="68.25001836489955" x2="151.11918673952937" y2="84.00002448653274" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyt8wsti4vp15s-9')"></line><line x1="96.55958630111111" y1="84.00001224326556" x2="123.83939005464704" y2="68.25001836489955" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyt8wsti4vp15s-11')"></line><line x1="69.17276818282303" y1="74.73537013707451" x2="90.99660553072891" y2="87.33537503438109" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyt8wsti4vp15s-13')"></line><line x1="69.27978961622877" y1="68.2500061216324" x2="96.55958630111111" y2="84.00001224326556" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyt8wsti4vp15s-15')"></line><line x1="69.27978961622877" y1="68.2500061216324" x2="69.27979668488234" y2="36.75000612163318" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyt8wsti4vp15s-17')"></line><line x1="42.000000000000014" y1="21" x2="69.27979668488234" y2="36.75000612163318" style="stroke-linecap:round;stroke-dasharray:none;stroke-width:1.26" stroke="url('#line-m6sn3pyt8wsti4vp15s-19')"></line></g><g><text x="201.74130131525487" y="26.25003672980148" class="element-m6sn3pyt8wsti4vp15s" fill="currentColor" style="
                text-anchor: start;
                writing-mode: horizontal-tb;
                text-orientation: mixed;
                letter-spacing: normal;
                direction: ltr;
            "><tspan style="
                unicode-bidi: plaintext;
                writing-mode: lr-tb;
                letter-spacing: normal;
                text-anchor: start;
            ">R7</tspan></text><text x="205.67880131525487" y="21.00003672980148" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="178.3989975617189" y="36.75003060816749" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="178.3989904930653" y="68.2500306081667" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="151.11918673952937" y="84.00002448653274" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="123.83939005464704" y="68.25001836489955" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="96.55958630111111" y="84.00001224326556" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="69.27978961622877" y="68.2500061216324" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="69.27979668488234" y="36.75000612163318" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text><text x="47.250000000000014" y="26.25" class="element-m6sn3pyt8wsti4vp15s" fill="currentColor" style="
                text-anchor: start;
                writing-mode: horizontal-tb;
                text-orientation: mixed;
                letter-spacing: normal;
                direction: rtl; unicode-bidi: bidi-override;
            "><tspan style="
                unicode-bidi: plaintext;
                writing-mode: lr-tb;
                letter-spacing: normal;
                text-anchor: start;
            ">R7</tspan></text><text x="42.000000000000014" y="21" class="debug" fill="#ff0000" style="
                font: 5px Droid Sans, sans-serif;
            "></text></g></svg>"/>


A leukotriene (LT)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0985.jpg?height=714&width=1125&top_left_y=510&top_left_x=500)
FIGURE 27.5 The naming system for eicosanoids.


Eicosanoid biosynthesis begins with the conversion of arachidonic acid to $\mathrm{PGH}_{2}$, catalyzed by the multifunctional PGH synthase (PGHS), also called cyclooxygenase (COX). There are two distinct enzymes, PGHS-1 and PGHS-2 (or COX-1 and COX-2), both of which accomplish the same reaction but appear to function independently. COX-1 carries out the normal physiological production of prostaglandins, and COX-2 produces additional prostaglandin in response to arthritis or other inflammatory conditions. Vioxx, Bextra, and several other drugs selectively inhibit the COX-2 enzyme but cause potentially serious heart and gastrointestinal problems in weakened patients. (See the Chapter 15 Chemistry Matters.)


PGHS accomplishes two transformations, an initial reaction of arachidonic acid with $\mathrm{O}_{2}$ to yield $\mathrm{PGG}_{2}$ and a subsequent reduction of the hydroperoxide group $(-\mathrm{OOH})$ to the alcohol $\mathrm{PGH}_{2}$. The sequence of steps involved in these transformations was shown in FIGURE 8.12.


Further processing of $\mathrm{PGH}_{2}$ leads to other eicosanoids. $\mathrm{PGE}_{2}$, for instance, arises by an isomerization of $\mathrm{PGH}_{2}$ catalyzed by PGE synthase (PGES) (FIGURE 27.6).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0986.jpg?height=752&width=1353&top_left_y=185&top_left_x=386)


FIGURE 27.6 Mechanism of the conversion of PGH $_{2}$ into PGE $_{2}$.
PROBLEM Assign $R$ or $S$ configuration to each chirality center in prostaglandin $\mathrm{E}_{2}$ (Figure 27.6), the most 27-5 abundant and biologically potent of mammalian prostaglandins.