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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
Structure of GLYCERYL 1-OLEATE

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-

HIDE SMILES / InChI
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q5EZ72
Gene ID: 303729.0
Gene Symbol: Enpp7
Target Organism: Rattus norvegicus (Rat)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Phorbol esters stimulate cyclic adenosine 3', 5'-monophosphate accumulation in hamster spermatozoa during in vitro capacitation.
1989 Feb
Serum albumin binds beta- and alpha-monoolein in vitro.
2001 Mar
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
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.
Name Type Language
GLYCERYL 1-OLEATE
Common Name English
9-OCTADECENOIC ACID (9Z)-, 2,3-DIHYDROXYPROPYL ESTER
Common Name English
1-MONO(CIS-9-OCTACENOYL)GLYCEROL
Common Name English
1-GLYCERYL MONOOLEATE
Systematic Name English
1-GLYCERYL OLEATE
Systematic Name English
NSC-406285
Code English
GLYCERYL MONOOLEATE [FHFI]
Common Name English
1-MONOOLEIN
Common Name English
GLYCEROL 1-MONOOLEATE
Common Name English
RAC-1-MONOOLEOYLGLYCEROL
Common Name English
.ALPHA.-MONOOLEIN
Common Name English
1-MONOOLEOYL-RAC-GLYCEROL
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C83486
Created by admin on Fri Dec 15 15:00:31 GMT 2023 , Edited by admin on Fri Dec 15 15:00:31 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C77467
Created by admin on Fri Dec 15 15:00:31 GMT 2023 , Edited by admin on Fri Dec 15 15:00:31 GMT 2023
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CAS
111-03-5
Created by admin on Fri Dec 15 15:00:31 GMT 2023 , Edited by admin on Fri Dec 15 15:00:31 GMT 2023
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DRUG BANK
DB13171
Created by admin on Fri Dec 15 15:00:31 GMT 2023 , Edited by admin on Fri Dec 15 15:00:31 GMT 2023
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NSC
406285
Created by admin on Fri Dec 15 15:00:31 GMT 2023 , Edited by admin on Fri Dec 15 15:00:31 GMT 2023
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DAILYMED
D3AEF6S35P
Created by admin on Fri Dec 15 15:00:31 GMT 2023 , Edited by admin on Fri Dec 15 15:00:31 GMT 2023
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CHEBI
75757
Created by admin on Fri Dec 15 15:00:31 GMT 2023 , Edited by admin on Fri Dec 15 15:00:31 GMT 2023
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ECHA (EC/EINECS)
203-827-7
Created by admin on Fri Dec 15 15:00:31 GMT 2023 , Edited by admin on Fri Dec 15 15:00:31 GMT 2023
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EPA CompTox
DTXSID3042003
Created by admin on Fri Dec 15 15:00:31 GMT 2023 , Edited by admin on Fri Dec 15 15:00:31 GMT 2023
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FDA UNII
D3AEF6S35P
Created by admin on Fri Dec 15 15:00:31 GMT 2023 , Edited by admin on Fri Dec 15 15:00:31 GMT 2023
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PUBCHEM
5283468
Created by admin on Fri Dec 15 15:00:31 GMT 2023 , Edited by admin on Fri Dec 15 15:00:31 GMT 2023
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RXCUI
1426374
Created by admin on Fri Dec 15 15:00:31 GMT 2023 , Edited by admin on Fri Dec 15 15:00:31 GMT 2023
PRIMARY RxNorm
CHEBI
75342
Created by admin on Fri Dec 15 15:00:31 GMT 2023 , Edited by admin on Fri Dec 15 15:00:31 GMT 2023
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MESH
C471272
Created by admin on Fri Dec 15 15:00:31 GMT 2023 , Edited by admin on Fri Dec 15 15:00:31 GMT 2023
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