Details
Stereochemistry | RACEMIC |
Molecular Formula | C21H40O4 |
Molecular Weight | 356.5399 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO
InChI
InChIKey=RZRNAYUHWVFMIP-KTKRTIGZSA-N
InChI=1S/C21H40O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h9-10,20,22-23H,2-8,11-19H2,1H3/b10-9-
Glyceryl 1-oleate (1-O-Oleyl-rac-glycerol, Glyceryl oleate, Monoolein), is a surfactant that releases free glycerol and oleic acid upon hydrolysis. Monoolein has been used in liquid crystal studies and research shows that in the presence of monoolein, the penetration of the drug cisplatin (sc-200896) is doubled. Monoolein (1-Oleoyl-rac-glycerol) is used in the development of monoolein-based nanoparticulate liquid dispersions as possible vehicles for drug delivery. Glyceryl oleate is the monoester of glycerin and oleic acid. It's part of the hair lipids and skin lipids and has re-fating properties. Used as emulsifier and nonionic co-surfactant in various skin and hair care products. Creates water-in-oil emulsions (HLB value 3.5) but can also be used as a co-emulsifier and thickener for oil-in-water formulations. Add to oil/emulsifier phase of formulas. Typical use level: 0.5-3%. If used in surfactant systems, typical use level is 0.5-1% which should still keep shampoos clear and transparent.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Q5EZ72 Gene ID: 303729.0 Gene Symbol: Enpp7 Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12056588 |
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Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18487046 |
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Target ID: CHEMBL3474 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18487046 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Phorbol esters stimulate cyclic adenosine 3', 5'-monophosphate accumulation in hamster spermatozoa during in vitro capacitation. | 1989 Feb |
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Serum albumin binds beta- and alpha-monoolein in vitro. | 2001 Mar |
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Metabolomic profile in pancreatic cancer patients: a consensus-based approach to identify highly discriminating metabolites. | 2016 Feb 2 |
Patents
Sample Use Guides
Typical use level: 0.5-3%. If used in surfactant systems, typical use level is 0.5-1% which should still keep shampoos clear and transparent.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12056588
Glyceryl 1-oleate (1-Monooleoyl-rac-glycerol), 1-monostearoyl-rac-glycerol, stearic acid, oleic acid, linoleic acid, linolenic acid, and arachidonic acid stimulated the activity of alkaline SMase at 0.4-0.8 mM concentrations but inhibited the enzyme at higher concentrations.
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C83486
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SUBSTANCE RECORD