Enanthic acid, also called heptanoic acid, is an organic compound composed of a seven-carbon chain terminating in a carboxylic acid functional group. It is a colorless oily liquid with an unpleasant, rancid odor.[1] It contributes to the odor of some rancid oils. It is slightly soluble in water, but very soluble in ethanol and ether. Salts and esters of enanthic acid are called enanthates or heptanoates.
The methyl ester of ricinoleic acid, obtained from castor bean oil, is the main commercial precursor to enanthic acid. It is pyrolyzed to the methyl ester of 10-undecenoic acid and heptanal, which is then air-oxidized to the carboxylic acid. Approximately 20,000 tons were consumed in Europe and US in 1980.[2]
Laboratory preparations of enanthic acid include permanganate oxidation of heptanal[3] and 1-octene.[4]
^David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2
^Donald G. Lee, Shannon E. Lamb, Victor S. Chang (1981). "Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate: Nonadecanoic Acid". Organic Syntheses. 60: 11. doi:10.15227/orgsyn.060.0011.{{cite journal}}: CS1 maint: multiple names: authors list (link)
enanthic, acid, also, called, heptanoic, acid, organic, compound, composed, seven, carbon, chain, terminating, carboxylic, acid, functional, group, colorless, oily, liquid, with, unpleasant, rancid, odor, contributes, odor, some, rancid, oils, slightly, solubl. Enanthic acid also called heptanoic acid is an organic compound composed of a seven carbon chain terminating in a carboxylic acid functional group It is a colorless oily liquid with an unpleasant rancid odor 1 It contributes to the odor of some rancid oils It is slightly soluble in water but very soluble in ethanol and ether Salts and esters of enanthic acid are called enanthates or heptanoates Enanthic acid 1 Names Preferred IUPAC name Heptanoic acid Other names Enthanoic acid Enthanylic acid Heptoic acid Heptylic acid Oenanthic acid Oenanthylic acid 1 Hexanecarboxylic acid C7 0 lipid numbers Identifiers CAS Number 111 14 8 Y 3D model JSmol Interactive image ChEBI CHEBI 45571 Y ChEMBL ChEMBL320358 Y ChemSpider 7803 Y DrugBank DB02938 Y ECHA InfoCard 100 003 490 KEGG C17714 Y PubChem CID 8094 UNII THE3YNP39D Y CompTox Dashboard EPA DTXSID2021600 InChI InChI 1S C7H14O2 c1 2 3 4 5 6 7 8 9 h2 6H2 1H3 H 8 9 YKey MNWFXJYAOYHMED UHFFFAOYSA N YInChI 1 C7H14O2 c1 2 3 4 5 6 7 8 9 h2 6H2 1H3 H 8 9 Key MNWFXJYAOYHMED UHFFFAOYAP SMILES O C O CCCCCC Properties Chemical formula C 7H 14O 2 Molar mass 130 187 g mol 1 Appearance colorless oily liquid Density 0 9181 g cm3 20 C Melting point 7 5 C 18 5 F 265 6 K Boiling point 223 C 433 F 496 K Solubility in water 0 2419 g 100 mL 15 C Magnetic susceptibility x 88 60 10 6 cm3 mol Hazards NFPA 704 fire diamond 320 Lethal dose or concentration LD LC LD50 median dose 6400 mg kg oral rat Related compounds Related compounds Hexanoic acid Octanoic acid Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Its name derives from the Latin oenanthe which is in turn derived from the Ancient Greek oinos wine and anthos blossom Contents 1 Production 2 Uses 3 Safety 4 See also 5 ReferencesProduction edit nbsp Ricinoleic acid a fatty acid obtained from castor bean oil also occurs as its methyl ester methyl ricinoleate which is the main precursor to enanthic acid The methyl ester of ricinoleic acid obtained from castor bean oil is the main commercial precursor to enanthic acid It is pyrolyzed to the methyl ester of 10 undecenoic acid and heptanal which is then air oxidized to the carboxylic acid Approximately 20 000 tons were consumed in Europe and US in 1980 2 Laboratory preparations of enanthic acid include permanganate oxidation of heptanal 3 and 1 octene 4 Uses editEnanthic acid is used in the preparation of esters such as ethyl enanthate which are used in fragrances and as artificial flavors Enanthic acid is used to esterify steroids in the preparation of drugs such as testosterone enanthate trenbolone enanthate drostanolone enanthate and methenolone enanthate Primobolan The triglyceride ester of enanthic acid is the triheptanoin which is used in certain medical conditions as a nutritional supplement Safety editEnanthic acid is toxic if swallowed and corrosive 5 See also editList of saturated fatty acids List of carboxylic acidsReferences edit a b Merck Index 11th Edition 4581 David J Anneken Sabine Both Ralf Christoph Georg Fieg Udo Steinberner Alfred Westfechtel Fatty Acids in Ullmann s Encyclopedia of Industrial Chemistry 2006 Wiley VCH Weinheim doi 10 1002 14356007 a10 245 pub2 John R Ruhoff 1936 N Heptanoic Acid Organic Syntheses 16 39 doi 10 15227 orgsyn 016 0039 Donald G Lee Shannon E Lamb Victor S Chang 1981 Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate Nonadecanoic Acid Organic Syntheses 60 11 doi 10 15227 orgsyn 060 0011 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Heptanoic Acid Pubchem Retrieved from https en wikipedia org w index php title Enanthic acid amp oldid 1189701289, wikipedia, wiki, book, books, library,
