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Elaidic acid

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Elaidic acid
Elaidic-acid-2D-skeletal-reverse.png
Elaidic-acid-from-xtal-3D-balls.png
Elaidic-acid-from-xtal-3D-vdW.png
Names
IUPAC name
(E)-octadec-9-enoic acid
Other names
(E)-9-octadecenoic acid
(9E)-octadecenoic acid
trans-9-octadecenoic acid
18:1 trans-9
C18:1 trans-9
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.642
KEGG
PubChem CID
UNII
  • InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+ checkY
    Key: ZQPPMHVWECSIRJ-MDZDMXLPSA-N checkY
  • InChI=1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+
    Key: ZQPPMHVWECSIRJ-MDZDMXLPBT
  • O=C(O)CCCCCCC/C=C/CCCCCCCC
Properties
C
18
H
34
O
2
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).
checkY verify (what is checkY☒N ?)

Elaidic acid is a chemical compound with the formula C
18
H
34
O
2
, specifically the fatty acid with structural formula HOOC−(CH2)7−CH=CH−(CH2)7−CH3, with the double bond (between carbon atoms 9 and 10) in trans configuration. It is a colorless oily solid. Its salts and esters are called elaidates.

Elaidic acid is an unsaturated trans fatty acid, with code C18:1 trans-9. This compound has attracted attention because it is a major trans fat found in hydrogenated vegetable oils, and trans fats have been implicated in heart disease.

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

Its name comes from the Ancient Greek word ἔλαιον (elaion), meaning oil.

Occurrence and bioactivity

Elaidic acid occurs naturally in small amounts in caprine and bovine milk (very roughly 0.1% of the fatty acids) and in some meats.

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

See also


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