Pimelic acid

Pimelic acid

Chembox new
Name = Pimelic acid
ImageFile = Pimelic acid.png ImageName = Pimelic acid
IUPACName = heptanedioic acid
Section1 = Chembox Identifiers
CASNo = 111-16-0
SMILES = OC(=O)CCCCCC(=O)O
Section2 = Chembox Properties
Formula = C7H12O4
MolarMass = 160.17 g/mol
Density = 1.28 g/cm3
MeltingPt = 103-105 °C
BoilingPt = Decomposes

Pimelic acid is the organic compound with the formula HO2C(CH2)5CO2H. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid called lysine. Pimelic acid is one methylene longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides. It is the final member of the mnemonic used to aid recollection of the order of the first six dicarboxylic acids using their common (not IUPAC) nomenclature: [http://en.wikipedia.org/wiki/Dicarboxylic_acid]

Pimelic acid has been synthesized from cyclohexanone and from salicylic acid. [Snyder, H. R.; Brooks, A. L.; Shapiro, S. H. "Pimelic Acid from Cyclohexanone" and Müller, A. "Pimelic Acid from Salicylic Acid"Organic Syntheses, Collected Volume 2, p.531 (1943).http://www.orgsyn.org/orgsyn/pdfs/CV2P0531.pdf] In the former route, the additional carbon is suppled by dimethyloxalate, which reacts with the enolate.

References


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Look at other dictionaries:

  • pimelic acid — pimelo rūgštis statusas T sritis chemija formulė HOOC(CH₂)₅COOH atitikmenys: angl. pimelic acid rus. пимелиновая кислота ryšiai: sinonimas – heptano dirūgštis …   Chemijos terminų aiškinamasis žodynas

  • pimelic acid — pə̇ˈmelik, pīˈ , mēl , lēk noun Etymology: pimelic International Scientific Vocabulary pimel (from Greek pimelē lard) + ic : a crystalline dicarboxylic acid HOOC(CH2)5COOH obtained usually by oxidation of unsaturated fats, castor oil, or… …   Useful english dictionary

  • pimelic acid — Heptanedioic acid; an intermediate in the oxidation of oleic acid in some microorganisms; a precursor of biotin. * * * pi·mel·ic acid pi .mel ik n a crystalline dicarboxylic acid C7H12O4 obtained usu. by oxidation of unsaturated fats or castor… …   Medical dictionary

  • pimelic acid — noun An acid, HOC(CH)COH, whose derivatives are involved in the biosynthesis of lysine. Syn: heptanedioic acid …   Wiktionary

  • pimelic acid — /peuh mel ik, mee lik/, Chem. a crystalline compound, C7H12O4, soluble in alcohol and ether: used in polymers and as a plasticizer. Also called heptanedioic acid. [1830 40; < Gk pimel(é) soft fat + IC] * * * …   Universalium

  • pimelic — adjective Of or pertaining to pimelic acid or its derivatives …   Wiktionary

  • Pimelic — Pi*mel ic (p[i^]*m[e^]l [i^]k), a. [Gr. pimelh fat.] (Chem.) (a) Pertaining to, or designating, a substance obtained from certain fatty substances, and subsequently shown to be a mixture of suberic and adipic acids. (b) Designating the acid… …   The Collaborative International Dictionary of English

  • Dicarboxylic acid — Dicarboxylic acids are organic compounds that contain two carboxylic acid functional groups. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC R COOH, where R may be an alkyl, alkenyl, alkynyl, or aryl group.… …   Wikipedia

  • Adipic acid — Chembox new Name = Adipic acid ImageFile = Adipic acid structure.png ImageName = Adipic acid ImageFile1 = Adipic acid 3d.png IUPACName = hexanedioic acid OtherNames = butane 1,4 dicarboxylic acid Section1 = Chembox Identifiers SMILES =… …   Wikipedia

  • Diaminopimelic acid — Diaminopimelic acid …   Wikipedia

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