Elaidic acid

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Elaidic acid
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 Edit this at Wikidata
KEGG
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
18H
34O
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).
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Elaidic acid is a chemical compound with the formula C
18H
34O
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 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.[1]

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

Etymology

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The name elaidic comes from the Ancient Greek word ἔλαιον (élaion), meaning oil.

Occurrence and bioactivity

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Elaidic acid occurs mostly in industrial hydrogenation of polyunsaturated fatty acids.[2] It's also present in small amounts in goat and cow milk (very roughly 0.1% of the fatty acids)[3] and in some meats.[4]

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

See also

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References

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  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. ^ Wendeu-Foyet, Gaëlle; Bellicha, Alice; Chajès, Véronique; Huybrechts, Inge; Bard, Jean-Marie; Debras, Charlotte; Srour, Bernard; Sellem, Laury; Fezeu, Léopold K.; Julia, Chantal; Kesse-Guyot, Emmanuelle; Agaësse, Cédric; Druesne-Pecollo, Nathalie; Galan, Pilar; Hercberg, Serge (2023). "Different Types of Industry-Produced and Ruminant Trans Fatty Acid Intake and Risk of Type 2 Diabetes: Findings From the NutriNet-Santé Prospective Cohort". Diabetes Care. 46 (2): 321–330. doi:10.2337/dc22-0900. PMID 36542554. S2CID 255041911.
  3. ^ 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.
  4. ^ Stillwell, William (2016). "Chapter 23. Membranes and Human Health". An Introduction to Biological Membranes – Composition, Structure and Function (2 ed.). Elsevier. doi:10.1016/B978-0-444-63772-7.00023-3.
  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.