phenylacetic acid phenylacetic acid phenylacetic acid (paa; conjugate base phenylacetate), also known by various synonyms, is an organic compound containing a phenyl functional group and a carboxylic acid functional group. it is a white solid with a strong honey-like odor. endogenously, it is a catabolite of phenylalanine. as a commercial chemical, because it can be used in the illicit production of phenylacetone (used in the manufacture of substituted amphetamines), it is subject to controls in countries including the united states and china. phenylacetic acid names preferred iupac name phenylacetic acid systematic iupac name phenylethanoic acid other names α-toluic acidbenzeneacetic acid2-phenylacetic acidβ-phenylacetic acid identifiers cas number 103-82-2 y 3d model (jsmol) interactive image 3dmet b02157 beilstein reference 1099647 chebi chebi:30745 y chembl chembl1044 y chemspider 10181341 y drugbank db09269 echa infocard 100.002.862 ec number 203-148-6 gmelin reference 68976 kegg c07086 pubchem cid 999 rtecs number aj2430000 unii er5i1w795a y comptox dashboard (epa) dtxsid2021656 inchi inchi=1s/c8h8o2/c9-8(10)6-7-4-2-1-3-5-7/h1-5h,6h2,(h,9,10) ykey: wljvxdmoqogphl-uhfffaoysa-n yinchi=1/c8h8o2/c9-8(10)6-7-4-2-1-3-5-7/h1-5h,6h2,(h,9,10)key: wljvxdmoqogphl-uhfffaoyar smiles o=c(o)cc1ccccc1 properties chemical formula c8h8o2 molar mass 136.15 g/mol appearance white solid odor honey-like density 1.0809 g/cm3 melting point 76 to 77 °c (169 to 171 °f; 349 to 350 k) boiling point 265.5 °c (509.9 °f; 538.6 k) solubility in water 15 g/l acidity (pka) 4.31 (h2o) magnetic susceptibility (χ) -82.72·10−6 cm3/mol hazards ghs labelling: pictograms signal word danger hazard statements h318, h319 precautionary statements p264, p280, p305+p351+p338, p310, p337+p313 nfpa 704 (fire diamond) 2 1 0 safety data sheet (sds) external msds related compounds related compounds benzoic acid, phenylpropanoic acid, cinnamic acid except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). y verify (what is yn ?) infobox references occurrence phenylacetic acid has been found to be an active auxin (a type of plant hormone), found predominantly in fruits. however, its effect is much weaker than the effect of the basic auxin molecule indole-3-acetic acid. in addition the molecule is naturally produced by the metapleural gland of most ant species and used as an antimicrobial. it is also the oxidation product of phenethylamine in humans following metabolism by monoamine oxidase and subsequent metabolism of the intermediate product, phenylacetaldehyde, by the aldehyde dehydrogenase enzyme; these enzymes are also found in many other organisms. preparation this compound may be prepared by the hydrolysis of benzyl cyanide: phenylacetic acid applications phenylacetic acid is used in some perfumes, as it possesses a honey-like odor even in low concentrations. it is also used in penicillin g production and diclofenac production. it is also employed to treat type ii hyperammonemia to help reduce the amounts of ammonia in a patient's bloodstream by forming phenylacetyl-coa, which then reacts with nitrogen-rich glutamine to form phenylacetylglutamine. this compound is then excreted from the patient's body. it's also used in the illicit production of phenylacetone, which is used in the manufacture of methamphetamine. the sodium salt of phenylacetic acid, sodium phenylacetate, is used as a pharmaceutical drug for the treatment of urea cycle disorders, including as the combination drug sodium phenylacetate/sodium benzoate (ammonul). phenylacetic acid is used in the preparation of several pharmaceutical drugs, including camylofin, bendazol, triafungin, phenacemide, lorcainide, phenindione, and cyclopentolate. in popular culture in the crime drama breaking bad, phenylacetic acid is featured twice as a precursor to methamphetamine, first in the episode titled "a no-rough-stuff-type deal", then in "salud". in the police drama s.w.a.t s6e14, phenylacetic acid is featured as a chemical needed to process a new drug called iso.