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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/04/17 05:21:44」(JST)

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Heptanoic acid, also called enanthic acid, is an organic compound composed of a seven-carbon chain terminating in a carboxylic acid. It is an 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.

Production and uses

The methyl ester of ricinoleic acid, obtained from castor bean oil is the main commercial precursor to heptanoic acid. It is pyrolyzed to the methyl ester of 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]

Ricinoleic acid is the main precursor to heptanoic acid.

Heptanoic acid is used in the preparation of esters, such as ethyl heptanoate, which are used in fragrances and as artificial flavors.

Heptanoic acid is used to esterify steroids in the preparation of drugs such as testosterone enanthate, trenbolone enanthate, drostanolone enanthate and methenolone enanthate (Primobolan). It is also one of many additives in cigarettes.

References

^ ^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

English Journal

A Clinical Quantitative Evaluation of Hepatobiliary Transport of [¹¹C]Dehydropravastatin in Humans Using Positron Emission Tomography.

Kaneko K1, Tanaka M1, Ishii A2, Katayama Y3, Nakaoka T1, Irie S1, Kawahata H2, Yamanaga T2, Wada Y3, Miyake T4, Toshimoto K5, Maeda K4, Cui Y3, Enomoto M2, Kawamura E2, Kawada N2, Kawabe J2, Shiomi S2, Kusuhara H4, Sugiyama Y5, Watanabe Y3.
Drug metabolism and disposition: the biological fate of chemicals.Drug Metab Dispos.2018 May;46(5):719-728. doi: 10.1124/dmd.118.080408. Epub 2018 Mar 19.
PMID 29555827

Controlling Ethanol Use in Chain Elongation by CO₂ Loading Rate.

Roghair M1, Hoogstad T1, Strik DPBTB1, Plugge CM2,3, Timmers PHA2,3, Weusthuis RA4, Bruins ME5, Buisman CJN1.
Environmental science & technology.Environ Sci Technol.2018 Feb 6;52(3):1496-1505. doi: 10.1021/acs.est.7b04904. Epub 2018 Jan 24.
PMID 29304274

Triheptanoin protects against status epilepticus-induced hippocampal mitochondrial dysfunctions, oxidative stress and neuronal degeneration.

Tan KN1, Simmons D1, Carrasco-Pozo C2,3, Borges K1.
Journal of neurochemistry.J Neurochem.2018 Feb;144(4):431-442. doi: 10.1111/jnc.14275. Epub 2018 Jan 3.
PMID 29222946

Japanese Journal

味噌汁中の香気成分の加熱に伴う変化(自然科学編)

石原和夫,佐藤彩乃,曽根英行
県立新潟女子短期大学研究紀要 45, 9-18, 2008
… 各味噌汁中で検出された主なエステル類はethyl acetate、ethyl heptanoate、ethyl lactateおよび2-methylbutyl acetate と3-methylbuty lacetateなどであり、量的にはethyl acetateは八丁味噌、ethyl heptanoate は越後味噌、ethyl lactateは信州味噌に多いことが認められた。 …
NAID 110006966741

Polar Organic Solvent Added to an Aqueous Solution Changes Hydrolytic Property of Lipase(Biochemistry & Molecular Biology)

TSUZUKI Wakako,UE Akemi,NAGAO Akihiko
Bioscience, biotechnology, and biochemistry 67(8), 1660-1666, 2003-08-23
… While hydrolysis by this lipase toward the substrates with a relatively weak hydrophobicity (4-metylumbelliferyl heptanoate and 4-methylumbelliferyl nanoate) was suppressed by these solvents. …
NAID 110002694284

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リンク元	「ヘプタン酸」「ヘプタン酸エステル」「heptanoic acid」

「ヘプタン酸」

Heptanoic acid^[1]
Names
	IUPAC name Heptanoic acid
	Other names Enanthic acid; Oenanthic acid; n-Heptylic acid; n-Heptoic acid
Identifiers
CAS Number	111-14-8
ChEBI	CHEBI:45571
ChEMBL	ChEMBL320358
ChemSpider	7803
DrugBank	DB02938
Jmol 3D image	Interactive graph
KEGG	C17714
PubChem	8094
UNII	THE3YNP39D
	InChI InChI=1S/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9) Key: MNWFXJYAOYHMED-UHFFFAOYSA-N ; InChI=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	C7H14O2
Molar mass	130.19 g·mol−1
Appearance	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)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references