Heptanoic acid

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.

Heptanoic acid[1]
Names
IUPAC name
Heptanoic acid
Other names
Enanthic acid; Oenanthic acid; n-Heptylic acid; n-Heptoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.490
KEGG
UNII
Properties
C7H14O2
Molar mass 130.187 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)
0.2419 g/100 mL (15 °C)
-88.60·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
Lethal dose or concentration (LD, LC):
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).
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Infobox references

Production
Ricinoleic acid is the main precursor to heptanoic acid.

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 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]

Uses

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).

The triglyceride ester of heptanoic acid is the triheptanoin, which is used in certain medical conditions as a nutritional supplement.

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See also

References
  1. Merck Index, 11th Edition, 4581
  2. 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
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