Elaidic acid

Elaidic acid
Names
	IUPAC name (E)-octadec-9-enoic acid
	Other names (E)-9-octadecenoic acid; (9E)-octadecenoic acid; 18:1 trans-9; C18:1 trans-9
Identifiers
CAS Number	112-79-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27997 ;
ChEMBL	ChEMBL460657 ;
ChemSpider	553123 ;
DrugBank	DB04224 ;
ECHA InfoCard	100.003.642
KEGG	C01712 ;
PubChem CID	637517;
UNII	4837010H8C ;
CompTox Dashboard (EPA)	DTXSID8058619 ;
	InChI 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+ Key: ZQPPMHVWECSIRJ-MDZDMXLPSA-N ; 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;
	SMILES O=C(O)CCCCCCC/C=C/CCCCCCCC;
Properties
Chemical formula	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)
Magnetic susceptibility (χ)	-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).

Elaidic acid is a chemical compound with the formula C
₁₈H
₃₄O
₂, specifically the fatty acid with structural formula HO(O=)C–(CH₂–)₇CH=CH–(CH₂–)₈H, 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.

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]

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.
^ 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.
^ William Stillwell (2016). Membranes and Human Health. An Introduction to Biological Membranes (Second ed.).
^ 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.
^ 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.

[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.

[Alonso-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.).

[Nasaruddin-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.

[pmid8018112-5] 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.

[1]

[2]

[3]

[4]

[5]

Names



IUPAC name (E)-octadec-9-enoic acid
Other names (E)-9-octadecenoic acid (9E)-octadecenoic acid 18:1 trans-9 C18:1 trans-9
Identifiers
CAS Number	112-79-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27997
ChEMBL	ChEMBL460657
ChemSpider	553123
DrugBank	DB04224
ECHA InfoCard	100.003.642
KEGG	C01712
PubChem CID	637517
UNII	4837010H8C
CompTox Dashboard (EPA)	DTXSID8058619
InChI 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+ Key: ZQPPMHVWECSIRJ-MDZDMXLPSA-N 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
SMILES O=C(O)CCCCCCC/C=C/CCCCCCCC
Properties
Chemical formula	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)
Magnetic susceptibility (χ)	-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).

Elaidic acid

Occurrence and bioactivity

See also

References