Heptanoic acid

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Heptanoic acid[1]
Heptanoic acid
Identifiers
CAS number 111-14-8 YesY
PubChem 8094
ChemSpider 7803 YesY
UNII THE3YNP39D YesY
DrugBank DB02938
KEGG C17714 YesY
ChEBI CHEBI:45571 YesY
ChEMBL CHEMBL320358 YesY
Jmol-3D images Image 1
Properties
Molecular formula C7H14O2
Molar mass 130.18 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 noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

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[edit]

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

  1. ^ a b 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