CAS 111-03-5 Glyceryl Monooleate (HCID 5283468)

Overview

1-oleoylglycerol is a 1-monoglyceride where the acyl group is oleoyl. It has a role as a plant metabolite. It is a 1-acylglycerol 18:1 and a monooleoylglycerol. It is functionally related to an oleic acid.

Names & identifiers

Preferred name: Glyceryl Monooleate
IUPAC: 2,3-dihydroxypropyl (Z)-octadec-9-enoate
English name: Glyceryl Monooleate
Molecular formula: C21H40O4
Molecular weight: 356.54

Names & synonyms

MonooleinGlyceryl monooleatealpha-MonooleinGLYCEROL MONOOLEATEGlycerol oleate25496-72-4Nikkol MGOMonoglyceryl oleateOleic monoglycerideGlycerine monooleateOleoylglycerolOlicine

Show more names

Glyceryl oleateGMO9-Octadecenoic acid (Z)-, 2,3-dihydroxypropyl ester1-Monooleoylglycerol1-OLEOYL-RAC-GLYCEROL1-OleoylglycerolAblunol GMO

Supeol1-Mono(cis-9-octacenoyl)glycerol2,3-dihydroxypropyl (Z)-octadec-9-enoateSinnoester ogcOleylmonoglycerideExcel O 95FDimodan LSQKEmalsy MO

Database identifiers

CAS: 111-03-5、25496-72-4
PubChem CID: 5283468
DTXSID: DTXSID3042003
ChEMBL: CHEMBL2075039、CHEMBL428593
ChEBI: CHEBI:75342
UNII: D3AEF6S35P
EC Number: 203-827-7、247-038-6
Nikkaji: J5.104G

Properties

Computed structural properties

XLogP: 6.5
Topological polar surface area: 66.8 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 19
Heavy atoms: 25
Formal charge: 0
Complexity: 315

Experimental & physicochemical properties

Chemical ClassesOther Uses -> Emulsifiers/Surfactants

LipidsLipids -> Glycerolipids [GL] -> Monoradylglycerols [GL01] -> Monoacylglycerols [GL0101]

Fragrances · 2 items

Fragrance Ingredient (9-Octadecenoic acid (Z)-, monoester with 1,2,3-propanetriol) -> IFRA transparency List

Fragrance Ingredient (Glyceryl monooleate) -> IFRA transparency List

SurfactantsSurfactant

OdorSWEET

TasteFATTY TASTE

Physicochemical properties

Melting point: 35 · 35-37 °C
Boiling point: 409.35 °C · 409.35°C (rough estimate)
Density: 0.9407 g/cm3 · 0.9407 g/cm3 (35 ºC)
refractive index: 1.46384 · 1.46384 (589.3 nm 35℃)
FEMA: 2526 · 2526 | GLYCERYL MONOOLEATE
Flash point: 180 °C · 180 °C
storage temp.: 2 · 2-8°C
solubility: 50 mg/mL, · chloroform: 50 mg/mL, clear, colorless
pka: 13.16 · 13.16±0.20(Predicted)
form: Solid
color: White to Off-White
Odor: bland fatty waxy
Odor Type: bland
biological source: synthetic (organic)
JECFA Number: 919 · 919
BRN: 1728976 · 1728976
Stability: Hygroscopic
Cosmetics Ingredients Functions: PERFUMINGSURFACTANT - EMULSIFYINGSKIN CONDITIONING - EMOLLIENT
Cosmetic Ingredient Review (CIR): Glyceryl Monooleate (111-03-5)
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-
InChIKey: RZRNAYUHWVFMIP-KTKRTIGZSA-N
SMILES: O=C(CCCCCCC/C=C\CCCCCCCC)OCC(O)CO
LogP: 6.71 · 6.71
CAS DataBase Reference: 111 · 111-03-5(CAS DataBase Reference)
FDA 21 CFR: 175.3 · 175.300; 175.320; 181.27;184.1323
EWG's Food Scores: 1 · 1
FDA UNII: 3 AEF6S35P · D3AEF6S35P
EPA Substance Registry System: Glycerol monooleate (111-03-5)
UNSPSC Code: 12352211 · 12352211
NACRES: 25 · NA.25
Symbol(GHS): 2 · GHS02,GHS07
Signal word: Danger
Hazard statements: 225 · H225-H302-H312-H332
Precautionary statements: 210 · P210-P280
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: F,Xn
Risk Statements: 11 · 11-20/21/22
Safety Statements: 36 · 36/37
RIDADR: 1282 · UN 1282 3/PG 2
WGK Germany: 1 · 1
F: 3 · 3
TSCA: TSCA listed
HS Code: 29161500 · 29161500
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 96.9% (492 of 508) of all reports.

Not Classified

Aggregated GHS information provided per 508 reports by companies from 5 notifications to the ECHA C&L Inventory.

This chemical does not meet GHS hazard criteria for 100% (260 of 260) of all reports.

Not Classified

Aggregated GHS information provided per 260 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 4 items

Chemical: 9-Octadecenoic acid, monoester with 1,2,3-propanetriol, (Z)-

9-Octadecenoic acid (9Z)-, monoester with 1,2,3-propanetriol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9-Octadecenoic acid (9Z)-, monoester with 1,2,3-propanetriol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

1-Glyceryl monooleate: Does not have an individual approval but may be used under an appropriate group standard

Glyceryl monooleate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 9-Octadecenoic acid, monoester with 1,2,3-propanetriol, (Z)-: Human health tier I assessment

Hazards SummaryMay cause mild irritation; [MSDSonline]

FDA Requirements · 2 items

SYNTHETIC FLAVOR INGREDIENTS- GLYCERYL MONOOLEATE: REGULATION 172.515.

REGULATION FDA 121.1164; LIMITATIONS: SYNTHETIC FLAVOR.

EPA Safer Chemical · 2 items

Chemical: Glyceryl monooleate

Chemical: Glyceryl monooleate [NF]

Hazard Classes and Categories · 2 items

Not Classified

Toxicology

Human Toxicity Excerpts · 2 items

TREATMENT OF HUMAN ERYTHROCYTE GHOST MEMBRANES WITH THE FUSOGENIC LIPID GLYCEROL MONOOLEATE INCREASED THE FLUIDITY OF THE MEMBRANE LIPIDS, BUT THE NONFUSOGENIC LIPID GLYCEROL MONOSTEARATE HAD NO EFFECT.

IF ANY OF THESE ESTERS IS SIGNIFICANTLY TOXIC, THE ACID PORTION MUST BE HELD RESPONSIBLE, NOT THE GLYCEROL. /GLYCEROL ESTERS/

Regulatory information

FDA Requirements · 2 items

SYNTHETIC FLAVOR INGREDIENTS- GLYCERYL MONOOLEATE: REGULATION 172.515.

REGULATION FDA 121.1164; LIMITATIONS: SYNTHETIC FLAVOR.

Safety data

F: 3
PPE: Eyeshields, Gloves, type N95 (US)
wgk: 1
tsca: TSCA listed
ridadr: UN 1282 3/PG 2
hs_code: 29161500
risk_code: 11-20/21/22
Signal word: Danger
Symbol(GHS): GHS02,GHS07
hazard_code: F,Xn
safety_code: 36/37
Storage Class: 11 - Combustible Solids
Hazard statements: H225-H302-H312-H332
Precautionary statements: P210-P280

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Used in foods, pharmaceuticals, cosmetics, rust-preventive oils, vinyl light stabilizers, odorless base paints, textile finishing, and flavoring; Used as emulsifier for liquid and paste waxes, polishes, and cleaners; [Hawley]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

SURFACE-ACTIVE AGENT IN FOODS, PHARMACEUTICALS AND COSMETICS, ODORLESS BASE PAINTS, IN RUST-PREVENTIVE OILS, TEXTILE FINISHING, AND VINYL LIGHT STABILIZERS; FLAVORING INGREDIENT

U.S. Exports · 2 items

(1972) No Data

(1975) No Data

U.S. Imports · 2 items

(1972) No Data

(1975) No Data

U.S. Production · 3 items

2023: 5,000,000 - <10,000,000 lb

(1972) 1.25X10+9 GRAMS

(1975) 1.71X10+9 GRAMS

Consumer UsesSurface modifier

Industry UsesLubricating agent

Applications · 4 items

UsesMonoglycerides fatty acid esters 93% 1-Oleoyl, 7% 2-oleoyl.

Usesglyceryl oleate is an emollient and stabilizer derived from olive oil. It is a water-in-oil emulsifier that allows for softer emulsions than glyceryl stearate.

UsesGlyceryl Monooleate is a flavoring agent that is prepared by esterification of commercial oleic acid that is derived either from edible sources or from tall oil fatty acids. It contains and glyceryl esters of fatty acids present in commercial oleic acid. The ingredient is also used as an adjuvant and as a solvent and vehicle.

General Description1-Oleoyl-rac-glycerol is commonly known as monoolein (MO). It is an amphiphilic molecule that is made up of a glycerol backbone and a hydrocarbon chain.