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 oily solid. Its salts and esters are called elaidates.
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| Names | |
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| IUPAC name
(E)-octadec-9-enoic acid
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| 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)
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| DrugBank | |
| ECHA InfoCard | 100.003.642 |
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PubChem CID
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CompTox Dashboard (EPA)
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| 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 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.
Its name comes from the Ancient Greek word ἔλαιον (elaion), meaning oil.
Occurrence and bioactivity
editElaidic acid occurs mostly in industrial hydrogenation of polyunsaturated fatty acids.[2] It's also present in small amounts in caprine and bovine 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
editReferences
edit- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.