Elaidic acid

Elaidic acid



IUPAC name (E)-octadec-9-enoic acid
Identifiers
CAS number	112-79-8^Y
PubChem	637517
ChemSpider	553123^Y
DrugBank	DB04224
KEGG	C01712^Y
ChEBI	CHEBI:27997^Y
ChEMBL	CHEMBL460657^Y
Jmol-3D images	Image 1
SMILES O=C(O)CCCCCCC/C=C/CCCCCCCC
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+^Y Key: ZQPPMHVWECSIRJ-MDZDMXLPSA-N^Y 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
Properties
Molecular formula	C₁₈H₃₄O₂
Molar mass	282.46 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Elaidic acid is the major trans fat found in hydrogenated vegetable oils and occurs in small amounts in caprine and bovine milk (very roughly 0.1 % of the fatty acids).^[1] It is the trans isomer of oleic acid. The name of the elaidinization reaction comes from elaidic acid.

Elaidic acid increases CETP activity, which in turn raises VLDL and lowers HDL cholesterol.^[2]

References

^ 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. PMID 10342226.
^ 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.

Lipids: fatty acids

Saturated	VFA: Acetic (C2) · Propionic (C3) · Butyric (C4) · Valeric (C5) · Caproic (C6) · Enanthic (C7) · Caprylic (C8) · Pelargonic (C9) · Capric (C10) · Undecylic (C11) · Lauric (C12) · Tridecylic (C13) · Myristic (C14) · Pentadecanoic (C15) · Palmitic (C16) · Margaric (C17) · Stearic (C18) · Nonadecylic (C19) · Arachidic (C20) · Heneicosylic (C21) · Behenic (C22) · Tricosylic (C23) · Lignoceric (C24) · Pentacosylic (C25) · Cerotic (C26) · Heptacosylic (C27) · Montanic (C28) · Nonacosylic (C29) · Melissic (C30) · Hentriacontylic (C31) · Lacceroic (C32) · Psyllic (C33) · Geddic (C34) · Ceroplastic (C35) · Hexatriacontylic (C36)

n−3 Unsaturated	α-Linolenic • Stearidonic • Eicosapentaenoic • Docosahexaenoic

n−6 Unsaturated	Linoleic • γ-Linolenic • Dihomo-γ-linolenic • Arachidonic

n−9 Unsaturated	Oleic • Elaidic • Eicosenoic • Erucic • Nervonic • Mead

biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i