U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Molecular Formula C21H40O4
Molecular Weight 356.5399
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 1
Optical Activity ( + / - )

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
Serum albumin binds beta- and alpha-monoolein in vitro.
2001 Mar
Thermal behaviour of cubic phases rich in 1-monooleoyl-rac-glycerol in the ternary system. 1-monooleoyl-rac-glycerol/n-octyl-beta-D-glucoside/water.
2003 Jan
Fucoxanthin Derivatives: Synthesis and their Chemical Properties.
2015
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:00:31 UTC 2023
Edited
by admin
on Fri Dec 15 15:00:31 UTC 2023
Record UNII
D3AEF6S35P
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 15:00:31 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C77467
Created by admin on Fri Dec 15 15:00:31 UTC 2023 , Edited by admin on Fri Dec 15 15:00:31 UTC 2023
PRIMARY
CAS
111-03-5
Created by admin on Fri Dec 15 15:00:31 UTC 2023 , Edited by admin on Fri Dec 15 15:00:31 UTC 2023
PRIMARY
DRUG BANK
DB13171
Created by admin on Fri Dec 15 15:00:31 UTC 2023 , Edited by admin on Fri Dec 15 15:00:31 UTC 2023
PRIMARY
NSC
406285
Created by admin on Fri Dec 15 15:00:31 UTC 2023 , Edited by admin on Fri Dec 15 15:00:31 UTC 2023
PRIMARY
DAILYMED
D3AEF6S35P
Created by admin on Fri Dec 15 15:00:31 UTC 2023 , Edited by admin on Fri Dec 15 15:00:31 UTC 2023
PRIMARY
CHEBI
75757
Created by admin on Fri Dec 15 15:00:31 UTC 2023 , Edited by admin on Fri Dec 15 15:00:31 UTC 2023
PRIMARY
ECHA (EC/EINECS)
203-827-7
Created by admin on Fri Dec 15 15:00:31 UTC 2023 , Edited by admin on Fri Dec 15 15:00:31 UTC 2023
PRIMARY
EPA CompTox
DTXSID3042003
Created by admin on Fri Dec 15 15:00:31 UTC 2023 , Edited by admin on Fri Dec 15 15:00:31 UTC 2023
PRIMARY
FDA UNII
D3AEF6S35P
Created by admin on Fri Dec 15 15:00:31 UTC 2023 , Edited by admin on Fri Dec 15 15:00:31 UTC 2023
PRIMARY
PUBCHEM
5283468
Created by admin on Fri Dec 15 15:00:31 UTC 2023 , Edited by admin on Fri Dec 15 15:00:31 UTC 2023
PRIMARY
RXCUI
1426374
Created by admin on Fri Dec 15 15:00:31 UTC 2023 , Edited by admin on Fri Dec 15 15:00:31 UTC 2023
PRIMARY RxNorm
CHEBI
75342
Created by admin on Fri Dec 15 15:00:31 UTC 2023 , Edited by admin on Fri Dec 15 15:00:31 UTC 2023
PRIMARY
MESH
C471272
Created by admin on Fri Dec 15 15:00:31 UTC 2023 , Edited by admin on Fri Dec 15 15:00:31 UTC 2023
PRIMARY