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SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description1,2-Dioleoylglycerol is a diacylglycerol (DG).It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis. Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol. Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase.Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position.
  • 1,2-Diolein
  • 9-octadecenoic acid (Z)-, 1-(hydroxymethyl)-1,2-ethanediyl ester
  • 1,2-Di-(9Z-octadecenoyl)-glycerol
  • 9-Octadecenoate (Z)-, 1-(hydroxymethyl)-1,2-ethanediyl ester
CAS number2442-61-7
WeightAverage: 620.986
Monoisotopic: 620.537975414
IUPAC Name1-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate
Traditional IUPAC Name1,2-diolein
Chemical FormulaC39H72O5
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
Sub ClassDiradylglycerols
Direct Parent1,2-diacylglycerols
Alternative Parents
  • 1,2-acyl-sn-glycerol
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Melting pointNot Available
Experimental Properties
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
Water Solubility1.2e-05 g/LALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity188.34 m³·mol⁻¹ChemAxon
Polarizability80.99 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • endoplasmic reticulum
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
Citicoline + 1,2-dioleoylglycerolPC(18:1(9Z)/18:1(9Z)) + Cytidine monophosphate
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00y0-1059006000-3019689598fb8240d444JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-3098021000-1a5a34a6735d5abcc767JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0109-3094330000-6bade453f84b10c69ae6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02ar-0094003000-9146bd1b0359fb8c9ea4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-1092000000-3355e19130f89cffb94dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2090000000-3b7e3e27a7543c24cac0JSpectraViewer
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Hjelmstad, R. H., Bell, R. M. (1987). "Mutants of Saccharomyces cerevisiae defective in sn-1,2-diacylglycerol cholinephosphotransferase. Isolation, characterization, and cloning of the CPT1 gene." J Biol Chem 262:3909-3917.3029130
Synthesis Reference:Not Available
External Links:
HMDB IDNot Available
Pubchem Compound ID5497164
Kegg IDNot Available
ChemSpider ID4593734
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available


General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. The multiple transmembrane domains and lumenal hydrophilic domains of the cholinephosphotransferase might participate in the transport process
Gene Name:
Uniprot ID:
Molecular weight:
CDP-choline + 1,2-diacylglycerol → CMP + a phosphatidylcholine.