{{chembox | Watchedfields = changed | verifiedrevid = 443854052 | Name = Enanthic acid | Reference = <ref name=Merck>''Merck Index'', 11th Edition, '''4581'''</ref> | ImageFile = Heptanoic_acid.png | ImageClass = skin-invert-image | ImageSize = 200px | ImageName = Heptanoic acid | PIN = Heptanoic acid | OtherNames = {{unbulleted list|Enthanoic acid|Enthanylic acid|Heptoic acid|Heptylic acid|Oenanthic acid|Oenanthylic acid|1-Hexanecarboxylic acid|C7:0 (lipid numbers)}} | Section1 = {{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 7803 | PubChem = 8094 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = THE3YNP39D | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C17714 | InChI = 1/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9) | InChIKey = MNWFXJYAOYHMED-UHFFFAOYAP | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 320358 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = MNWFXJYAOYHMED-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 111-14-8 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB02938 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 45571 | SMILES = O=C(O)CCCCCC }} | Section2 = {{Chembox Properties | Appearance = colorless oily liquid | C=7|H=14|O=2 | Density = 0.9181 g/cm<sup>3</sup> (20 °C) | Solubility = 0.2419 g/100 mL (15 °C) | MeltingPtC = -7.5 | BoilingPtC = 223 | MagSus = −88.60·10<sup>−6</sup> cm<sup>3</sup>/mol }} | Section7 = {{Chembox Hazards | ExternalSDS = | FlashPtC = | FlashPt_ref = | AutoignitionPtC = | AutoignitionPt_ref = | ExploLimits = | NFPA-H = 3 | NFPA-F = 2 | NFPA-R = 0 | LD50 = 6400 mg/kg (oral, rat) | GHSPictograms = {{GHS05}}<ref name=PubChem>{{Cite web |title=Heptanoic Acid - Pubchem |url=https://pubchem.ncbi.nlm.nih.gov/compound/Heptanoic-acid}}</ref> | GHSSignalWord = Danger<ref name=PubChem/> | HPhrases = {{H-phrases|314}}<ref name=PubChem/> | PPhrases = {{P-phrases|261|271|280|303+361+353|304+340+310|305+351+338}}<ref>{{Cite web |title=Heptanoic acid |url=https://www.sigmaaldrich.com/product/aldrich/75190 |access-date=2025-03-29 |website=Sigma-Aldrich}}</ref> }} | Section8 = {{Chembox Related | OtherCompounds = Hexanoic acid, Octanoic acid }} }}
'''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.<ref name=Merck/> 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'''.
Its name derives from the Latin ''oenanthe'' which is in turn derived from the Ancient Greek ''oinos'' "wine" and ''anthos'' "blossom."
==Production== [[File:Ricinoleic acid.svg|class=skin-invert-image|thumb| left|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.<ref name=Ullmann>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}}</ref>
Laboratory preparations of enanthic acid include permanganate oxidation of heptanal<ref>{{cite journal |doi=10.15227/orgsyn.016.0039|author=John R. Ruhoff|title=N-Heptanoic Acid |journal=Organic Syntheses |year=1936 |volume=16 |page=39 }}</ref> and 1-octene.<ref>{{cite journal |doi=10.15227/orgsyn.060.0011|title=Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate: Nonadecanoic Acid |journal=Organic Syntheses |year=1981 |volume=60 |page=11|author=Donald G. Lee, Shannon E. Lamb, Victor S. Chang}}</ref>
==Uses== Enanthic acid is used in the preparation of esters, such as ethyl enanthate, which are used as artificial flavors. Enanthic acid is used to esterify anabolic steroids in the preparation of drugs such as testosterone enanthate, trenbolone enanthate, drostanolone enanthate, and methenolone enanthate.
The triglyceride of enanthic acid is known as triheptanoin, which is a medical food.
== Safety == Enanthic acid is corrosive.<ref name=PubChem/>
==See also== * List of saturated fatty acids * List of carboxylic acids
==References== {{Reflist}}
{{Fatty acids}}
Category:Alkanoic acids Category:Fatty acids Category:Foul-smelling chemicals