Enanthic acid[1]
Heptanoic acid
Names
Preferred IUPAC name
Heptanoic acid
Other names
Enthanoic acid; Enthanylic acid; Heptoic acid; Heptylic acid; Oenanthic acid; Oenanthylic acid; 1-Hexanecarboxylic acid; C7:0 (lipid numbers)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.490 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9) checkY
    Key: MNWFXJYAOYHMED-UHFFFAOYSA-N checkY
  • InChI=1/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9)
    Key: MNWFXJYAOYHMED-UHFFFAOYAP
  • O=C(O)CCCCCC
Properties
C7H14O2
Molar mass 130.187 g·mol−1
Appearance colorless 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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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 fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
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).
checkY verify (what is checkY☒N ?)

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.[1] 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

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.[2]

Laboratory preparations of enanthic acid include permanganate oxidation of heptanal[3] and 1-octene.[4]

Uses

Enanthic acid is used in the preparation of esters, such as ethyl enanthate, which are used in fragrances and as artificial flavors. Enanthic 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 enanthic acid is the triheptanoin, which is used in certain medical conditions as a nutritional supplement.

Safety

Enanthic acid is toxic if swallowed and corrosive.[5]

See also

References

  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
  3. ^ John R. Ruhoff (1936). "N-Heptanoic Acid". Organic Syntheses. 16: 39. doi:10.15227/orgsyn.016.0039.
  4. ^ Donald G. Lee, Shannon E. Lamb, Victor S. Chang (1981). "Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate: Nonadecanoic Acid". Organic Syntheses. 60: 11. doi:10.15227/orgsyn.060.0011.((cite journal)): CS1 maint: multiple names: authors list (link)
  5. ^ "Heptanoic Acid - Pubchem".