Elaidic acid

Elaidic acid is the organic compound with the formula CH3(CH2)7CHCH(CH2)7CO2H. Classified as an unsaturated trans fatty acid, it is a colorless oily solid. This compound has attracted attention because it is a major trans fat found in hydrogenated vegetable oils, and trans fats are implicated in heart disease.[1] The salts and esters of elaidic acid are called elaidates.

Elaidic acid
Names
IUPAC name
(E)-octadec-9-enoic acid
Other names
(E)-9-Octadecenoic acid,
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.642
KEGG
UNII
Properties
C18H34O2
Molar mass 282.46 g/mol
Appearance colorless waxy solid
Density 0.8734 g/cm3
Melting point 45 °C (113 °F)
-204.8·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

It is the trans isomer of oleic acid. The name of the elaidinization reaction comes from elaidic acid.

Occurrence and bioactivity

Elaidic acid occurs naturally in small amounts in caprine and bovine milk (very roughly 0.1% of the fatty acids)[2] and in some meats.[3] It also comprises 2.50% of the fats from the fruit of the durian species Durio graveolens.[4]

Elaidic acid increases plasma cholesterylester transfer protein (CETP) activity which lowers HDL cholesterol.[5]

See also

References
  1. Tardy, Anne-Laure; Morio, Béatrice; Chardigny, Jean-Michel; Malpuech-Brugère, Corinne (2011). "Ruminant and industrial sources of trans-fat and cardiovascular and diabetic diseases". Nutrition Research Reviews. 24 (1): 111–7. doi:10.1017/S0954422411000011. PMID 21320382.
  2. Alonso L, Fontecha J, Lozada L, Fraga MJ, Juárez M (1999). "Fatty acid composition of caprine milk: major, branched-chain, and trans fatty acids". J. Dairy Sci. 82 (5): 878–84. doi:10.3168/jds.S0022-0302(99)75306-3. hdl:10261/113439. PMID 10342226.
  3. William Stillwell (2016). Membranes and Human Health. An Introduction to Biological Membranes (Second ed.).
  4. Nasaruddin, Mohd hanif; Noor, Noor Qhairul Izzreen Mohd; Mamat, Hasmadi (2013). "Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah" [Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)] (PDF). Sains Malaysiana (in Malay). 42 (9): 1283–1288. ISSN 0126-6039. OCLC 857479186. Retrieved 28 November 2017.
  5. Abbey M, Nestel PJ (1994). "Plasma cholesteryl ester transfer protein activity is increased when trans-elaidic acid is substituted for cis-oleic acid in the diet". Atherosclerosis. 106 (1): 99–107. doi:10.1016/0021-9150(94)90086-8. PMID 8018112.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.