capric acid capric acid capric acid, also known as decanoic acid or decylic acid, is a saturated fatty acid, medium-chain fatty acid (mcfa), and carboxylic acid. its formula is ch3(ch2)8cooh. salts and esters of decanoic acid are called caprates or decanoates. the term capric acid is derived from the latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats. not to be confused with caproic acid or caprylic acid. decanoic acid names preferred iupac name decanoic acid other names caprinic acid; caprynic acid; decoic acid; decylic acid; 1-nonanecarboxylic acid; c10:0 (lipid numbers) identifiers cas number 334-48-5 y1002-62-6 (sodium salt) y 3d model (jsmol) interactive image chebi chebi:30813 y chembl chembl107498 y chemspider 2863 y drugbank db03600 n echa infocard 100.005.798 ec number 206-376-4 iuphar/bps 5532 kegg c01571 y pubchem cid 2969 rtecs number hd9100000 unii 4g9edb6v73 y4i820xkv2a (sodium salt) y comptox dashboard (epa) dtxsid9021554 inchi inchi=1s/c10h20o2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9h2,1h3,(h,11,12) ykey: ghvnfzfcnzkvnt-uhfffaoysa-n yinchi=1/c10h20o2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9h2,1h3,(h,11,12)key: ghvnfzfcnzkvnt-uhfffaoyac smiles o=c(o)ccccccccc properties chemical formula c10h20o2 molar mass 172.268 g·mol−1 appearance white crystals odor strong rancid and unpleasant density 0.893 g/cm3 (25 °c) 0.8884 g/cm3 (35.05 °c) 0.8773 g/cm3 (50.17 °c) melting point 31.6 °c (88.9 °f; 304.8 k) boiling point 268.7 °c (515.7 °f; 541.8 k) solubility in water 0.015 g/100 ml (20 °c) solubility soluble in alcohol, ether, chcl3, c6h6, cs2, acetone log p 4.09 vapor pressure 4.88·10−5 kpa (25 °c) 0.1 kpa (108 °c) 2.03 kpa (160 °c) acidity (pka) 4.9 thermal conductivity 0.372 w/m·k (solid) 0.141 w/m·k (liquid) refractive index (nd) 1.4288 (40 °c) viscosity 4.327 cp (50 °c) 2.88 cp (70 °c) structure crystal structure monoclinic (−3.15 °c) space group p21/c lattice constant a = 23.1 å, b = 4.973 å, c = 9.716 åα = 90°, β = 91.28°, γ = 90° thermochemistry heat capacity (c) 475.59 j/mol·k std enthalpy offormation (δfh⦵298) −713.7 kj/mol std enthalpy ofcombustion (δch⦵298) 6079.3 kj/mol hazards occupational safety and health (ohs/osh): main hazards medium toxicity ingestion hazards may be toxic inhalation hazards may cause irritation skin hazards may be toxic on contact ghs labelling: pictograms signal word warning hazard statements h315, h319, h335 precautionary statements p261, p305+p351+p338 nfpa 704 (fire diamond) 2 1 0 flash point 110 °c (230 °f; 383 k) lethal dose or concentration (ld, lc): ld50 (median dose) 10 g/kg (rats, oral) safety data sheet (sds) external msds related compounds related fatty acids nonanoic acid, undecanoic acid related compounds decanoldecanal except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). n verify (what is yn ?) infobox references occurrence capric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4%), otherwise it is uncommon in typical seed oils. it is found in the milk of various mammals and to a lesser extent in other animal fats. two other acids are named after goats: caproic acid (a c6:0 fatty acid) and caprylic acid (a c8:0 fatty acid). along with capric acid, these total 15% in goat milk fat. production capric acid can be prepared from oxidation of the primary alcohol decanol by using chromium trioxide (cro3) oxidant under acidic conditions. neutralization of capric acid or saponification of its triglyceride esters with sodium hydroxide yields sodium caprate, ch3(ch2)8co−2na+. this salt is a component of some types of soap. uses capric acid is used in the manufacture of esters for artificial fruit flavors and perfumes. it is also used as an intermediate in chemical syntheses. it is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals. pharmaceuticals caprate ester prodrugs of various pharmaceuticals are available. since capric acid is a fatty acid, forming a salt or ester with a drug will increase its lipophilicity and its affinity for adipose tissue. since distribution of a drug from fatty tissue is usually slow, one may develop a long-acting injectable form of a drug (called a depot injection) by using its caprate form. some examples of drugs available as a caprate ester include nandrolone, fluphenazine, bromperidol, and haloperidol. effects capric acid acts as a non-competitive ampa receptor antagonist at therapeutically relevant concentrations, in a voltage- and subunit-dependent manner, and this is sufficient to explain its antiseizure effects. this direct inhibition of excitatory neurotransmission by capric acid in the brain contributes to the anticonvulsant effect of the mct ketogenic diet. decanoic acid and the ampa receptor antagonist drug perampanel act at separate sites on the ampa receptor, and so it is possible that they have a cooperative effect at the ampa receptor, suggesting that perampanel and the ketogenic diet could be synergistic. capric acid may be responsible for the mitochondrial proliferation associated with the ketogenic diet, and that this may occur via pparγ receptor agonism and its target genes involved in mitochondrial biogenesis. complex i activity of the electron transport chain is substantially elevated by decanoic acid treatment. it should however be noted that orally ingested medium chain fatty acids would be very rapidly degraded by first-pass metabolism by being taken up in the liver via the portal vein, and are quickly metabolized via coenzyme a intermediates through β-oxidation and the citric acid cycle to produce carbon dioxide, acetate and ketone bodies. whether the ketones β-hydroxybutryate and acetone have direct antiseizure activity is unclear.