Record Information
Creation date2015-10-09 22:33:34 UTC
Update date2017-01-19 02:36:42 UTC
FoodComEx IDPC000948
FoodDB RecordFDB027522
Chemical Information
DescriptionCE(18:3(9Z,12Z,15Z)) is a cholesterol fatty acid ester or simply a cholesterol ester (CE). Cholesterol esters are cholesterol molecules with long-chain fatty acids linked to the hydroxyl group. They are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesterol esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of C18 fatty acids. Cholesterol esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesterol esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesterol esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesterol esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesterol esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesterol esters from CoA esters of fatty acids and cholesterol. Cholesterol ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells. [HMDB]
CAS Number2545-22-4
(3b) Cholest 5 en 3 ol (Z,Z,Z) octadecatrienoatehmdb
(3b) Cholest 5 en 3 ol (Z,Z,Z) octadecatrienoic acidhmdb
18:3 Cholesteryl esterChEBI
18:3(9Z,12Z,15Z) cholesterol esterhmdb
Cholest 5 en 3beta yl (Z,Z,Z) octadeca 9,12,15 trien 1 oatehmdb
Cholest 5 en 3beta yl (Z,Z,Z) octadeca 9,12,15 trien 1 oic acidhmdb
cholesterol 1-(9Z,12Z,15Z-octadeatrienoatehmdb
cholesterol 1-(9Z,12Z,15Z-octadeatrienoate)hmdb
cholesterol 1-(9Z,12Z,15Z-octadeatrienoic acidhmdb
cholesterol 1-(9Z,12Z,15Z-octadeatrienoic acid)hmdb
cholesterol 1-a-linolenoatehmdb
cholesterol 1-a-linolenoic acidhmdb
cholesterol 1-alpha-linolenoatehmdb
cholesterol 1-alpha-linolenoic acidhmdb
Cholesterol a linolenatehmdb
Cholesterol alpha linolenatehmdb
Cholesterol Ester(18:3n3/0:0)hmdb
Cholesterol Ester(18:3w3/0:0)hmdb
Cholesterol linolenatehmdb
Cholesterol octadecatrienoatehmdb
Cholesterol octadecatrienoic acidhmdb
Cholesteryl (9Z,12Z,15Z)-octadeca-9,12,15-trienoateChEBI
Cholesteryl (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acidGenerator
cholesteryl 1-(9Z,12Z,15Z-octadeatrienoatehmdb
cholesteryl 1-(9Z,12Z,15Z-octadeatrienoate)hmdb
cholesteryl 1-(9Z,12Z,15Z-octadeatrienoic acidhmdb
cholesteryl 1-(9Z,12Z,15Z-octadeatrienoic acid)hmdb
cholesteryl 1-a-linolenoatehmdb
cholesteryl 1-a-linolenoic acidhmdb
cholesteryl 1-alpha-linolenoatehmdb
cholesteryl 1-alpha-linolenoic acidhmdb
Cholesteryl linolenatehmdb
Cholesteryl linolenic acidhmdb
Cholesteryl octadecatrienoatehmdb
Cholesteryl octadecatrienoic acidhmdb
Linolenic acid cholesteryl esterhmdb
Chemical FormulaC45H74O2
IUPAC name(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl octadeca-9,12,15-trienoate
InChI IdentifierInChI=1S/C45H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h8-9,11-12,14-15,26,35-36,38-42H,7,10,13,16-25,27-34H2,1-6H3/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1
Isomeric SMILES[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@]([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCCC=CCC=CCC=CCC
Average Molecular Weight647.0679
Monoisotopic Molecular Weight646.568881612
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentCholesteryl esters
Alternative Parents
  • Cholesteryl ester
  • Cholesterol
  • Cholestane-skeleton
  • Delta-5-steroid
  • Octadecanoid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 500 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez
Commercial Vendors
AKSci P591
Cayman Chemical 22596
Toronto Research Chemicals C432588