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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ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.003.642 |
KEGG | |
PubChem CID
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UNII | |
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 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.
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.
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Cis & Trans Fatty acids
Transcription
Occurrence and bioactivity
Elaidic 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
References
- ^ 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.