Cholesteryl Oleate

HCID 5283632

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Basic information

CAS: 303-43-5
Standard SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@@H]32)C1
InChIKey: RJECHNNFRHZQKU-RMUVNZEASA-N
Molecular formula: C45H78O2
Average molar mass: 651.1 g/mol
Monoisotopic mass: 650.60018174

Overview

Cholesteryl oleate is the (Z)-stereoisomer of cholesteryl octadec-9-enoate. It has a role as a mouse metabolite. It is a CE(18:1) and a cholesteryl octadec-9-enoate. It is functionally related to an oleic acid.

Names & identifiers

Preferred name: Cholesteryl Oleate
IUPAC: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (Z)-octadec-9-enoate
English name: Cholesteryl oleate
Molecular formula: C45H78O2
Molecular weight: 651.12

Names & synonyms

Cholesteryl oleateOleoylcholesterol303-43-5Cholesterol OleateCholesteryl cis-9-octadecenoateOleic acid cholesteryl esterCholest-5-en-3-beta-yl oleateCholesterol, oleate3DPK9KFN2MDTXSID901014621YOFCO LC-CO-D[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (Z)-octadec-9-enoate

Show more names

C18:1 CE18:1 Chol EstercholestreyloleateCholestereyl oleateCholesteroyl-oleateCHOLESTERYL OLEATE 97%CHOLESTERYL OLEATE(RG)

Cholest-5-en-3-ol (3beta)-, 3-[(9Z)-9-octadecenoate]CHEBI:46898NSC-18186Cholest-5-en-3-ol (3beta)-, (9Z)-9-octadecenoateCholest-5-en-3-ol (3beta)-, 3-((9Z)-9-octadecenoate)((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((2R)-6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-3-yl) (Z)-octadec-9-enoateRefChem:125721DTXCID601437167

Database identifiers

CAS: 303-43-5
PubChem CID: 5283632
DTXSID: DTXSID901014621
ChEMBL: CHEMBL1097567
ChEBI: CHEBI:46898
UNII: 3DPK9KFN2M
EC Number: 206-142-1
Nikkaji: J193.711A

Properties

Computed structural properties

XLogP: 16.6
Topological polar surface area: 26.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 22
Heavy atoms: 47
Formal charge: 0
Complexity: 976

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Cholesterol and Derivatives

LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Steryl esters [ST0102]

CosmeticsSkin conditioning

Physical DescriptionWhite waxy solid; Odorless; [Alfa Aesar MSDS]

Collision Cross Section · 2 items

289.9 Å² [M+NH4]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

282.99 Å² [M+NH4]+ [CCS Type: TIMS; Method: single field calibrated]

Physicochemical properties

Melting point: 44 · 44-47 °C (lit.)
Boiling point: 617.95 °C · 617.95°C (rough estimate)
Density: 0.9287 · 0.9287 (rough estimate)
refractive index: -20 ° · -20 ° (C=2, THF)
Flash point: 230 °F · >230 °F
storage temp.: -20 °C · -20°C
solubility: 0.1 g/mL, · chloroform: 0.1 g/mL, clear, colorless
form: Solid
color: White to Off-White
biological source: synthetic (organic)
BRN: 2343071 · 2343071
Cosmetics Ingredients Functions: SKIN CONDITIONING
InChIKey: RJECHNNFRHZQKU-RMUVNZEASA-N
SMILES: [H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)O[C@H]1CC[C@@]2(C)C(C1)=CC[C@]3([H])[C@]2([H])CC[C@]4(C)[C@]([H])(CC[C@@]34[H])[C@H](C)CCCC(C)C
LogP: 18.284 · 18.284 (est)
CAS DataBase Reference: 303 · 303-43-5(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 3 DPK9KFN2M · 3DPK9KFN2M
NIST Chemistry Reference: Cholesteryl oleate(303-43-5)
EPA Substance Registry System: -5 · Cholest-5-en-3-ol (3.beta.)-, (9Z)-9-octadecenoate (303-43-5)
UNSPSC Code: 41141804 · 41141804
NACRES: 77 · NA.77
PPE: 95 · Eyeshields, Gloves, type N95 (US)
WGK Germany: 3 · 3
TSCA: TSCA listed
HazardClass: IRRITANT
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Hazard information

Regulatory Information · 2 items

Chemical: Cholest-5-en-3-ol, 9-octadecenoate, (3.beta.)-,(Z)-

Cholest-5-en-3-ol (3.beta.)-, (9Z)-9-octadecenoate: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryMay cause irritation; [Alfa Aesar MSDS]

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
tsca: TSCA listed
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids

Chemistry & industry

Uses & manufacturing

Use ClassificationCosmetics -> Skin conditioning

General Manufacturing InformationCholest-5-en-3-ol (3.beta.)-, 3-[(9Z)-9-octadecenoate]: ACTIVE

Applications

DescriptionCholesteryl oleate is a cholesterol ester. It has been used in the generation of nanoparticles and liposomes for drug delivery.

UsesCholesteryl oleate was used to study the ability of silicone hydrogel contact lenses to absorb tear lipids, cholesterol and cholesterol esters. It was also used in the development of amperometric cholesterol biosensors.