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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 415519901 |
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| verifiedrevid = 443854052 |
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| Name = Heptanoic acid |
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| Name = Enanthic acid |
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| Reference=<ref name=Merck>'']'', 11th Edition, '''4581'''</ref> |
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| Reference=<ref name=Merck>'']'', 11th Edition, '''4581'''</ref> |
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| ImageFile = Heptanoic_acid.png |
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| ImageFile = Heptanoic_acid.png |
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| ImageSize = 200px |
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| ImageSize = 200px |
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| ImageName = Heptanoic acid |
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| ImageName = Heptanoic acid |
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| IUPACName = Heptanoic acid |
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| PIN = Heptanoic acid |
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| OtherNames=Enanthic acid; Oenanthic acid; ''n''-Heptylic acid; ''n''-Heptoic acid |
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| OtherNames= Enthanoic acid; Enthanylic acid; Heptoic acid; Heptylic acid; Oenanthic acid; Oenanthylic acid; 1-Hexanecarboxylic acid; C7:0 (]) |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 111-14-8 |
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| CASNo = 111-14-8 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB02938 |
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| DrugBank = DB02938 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 45571 |
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| ChEBI = 45571 |
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| SMILES = O=C(O)CCCCCC |
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| SMILES = O=C(O)CCCCCC |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Appearance = Oily liquid |
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| Appearance = colorless oily liquid |
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| C=7|H=14|O=2 |
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| C=7|H=14|O=2 |
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| Density = 0.9181 g/cm<sup>3</sup> (20 °C) |
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| Density = 0.9181 g/cm<sup>3</sup> (20 °C) |
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| Solubility = 0.2419 g/100 mL (15 °C) |
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| Solubility = 0.2419 g/100 mL (15 °C) |
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| MeltingPtC = -7.5 |
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| MeltingPtC = -7.5 |
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| BoilingPtC = 223 |
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| BoilingPtC = 223 |
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| MagSus = −88.60·10<sup>−6</sup> cm<sup>3</sup>/mol |
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|Section7={{Chembox Hazards |
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| ExternalSDS = |
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| GHSSignalWord = |
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| HPhrases = |
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| PPhrases = |
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| FlashPtC = |
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| FlashPt_ref = |
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| AutoignitionPtC = |
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| AutoignitionPt_ref = |
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| ExploLimits = |
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| NFPA-H = 3 |
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| NFPA-F = 2 |
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| NFPA-R = 0 |
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| LD50 = 6400 mg/kg (oral, rat) |
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|Section8={{Chembox Related |
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| OtherCompounds = ], ] |
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'''Heptanoic acid''', also called '''enanthic acid''', is an ] composed of a seven-carbon chain terminating in a ]. It is an 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. |
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'''Enanthic acid''', also called '''heptanoic acid''', is an ] composed of a seven-carbon chain terminating in a ] functional group. It is a colorless oily liquid with an unpleasant, ] odor.<ref name=Merck/> It contributes to the odor of some rancid oils. It is slightly soluble in water, but very soluble in ] and ether. ] and ]s of enanthic acid are called '''enanthates''' or '''heptanoates'''. |
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Its name derives from the ] '']'' which is in turn derived from the ] ''oinos'' "wine" and ''anthos'' "blossom." |
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Heptanoic acid is used in the preparation of ]s, such as ], which are used in fragrances and as artificial flavors. |
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==Production== |
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It is also one of many ] |
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], a fatty acid obtained from ], also occurs as its methyl ester, ], which is the main precursor to enanthic acid.]] |
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The methyl ester of ], obtained from ], is the main commercial precursor to enanthic acid. It is pyrolyzed to the methyl ester of ] and ], 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> |
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Laboratory preparations of enanthic acid include permanganate oxidation of ]<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 ].<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> |
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==References== |
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{{reflist}} |
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==Uses== |
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Enanthic acid is used in the preparation of esters, such as ], which are used in fragrances and as artificial flavors. Enanthic acid is used to ] steroids in the preparation of drugs such as ], ], ], and ] (Primobolan). |
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The ] ester of enanthic acid is the ], which is used in certain medical conditions as a nutritional supplement. |
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== Safety == |
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Enanthic acid is toxic if swallowed and corrosive.<ref>{{Cite web |title=Heptanoic Acid - Pubchem |url=https://pubchem.ncbi.nlm.nih.gov/compound/Heptanoic-acid}}</ref> |
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==See also== |
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* ] |
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* ] |
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==References== |
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{{Reflist}} |
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{{Fatty acids}} |
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{{Fatty acids}} |
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