Cholesteryl Linoleate

HCID 5287939

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Basic information

CAS: 604-33-1
Standard SMILES: CCCCC/C=C\C/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: NAACPBBQTFFYQB-LJAITQKLSA-N
Molecular formula: C45H76O2
Average molar mass: 649.1 g/mol
Monoisotopic mass: 648.58453166

Overview

Cholesteryl linoleate is the (9Z,12Z)-stereoisomer of cholesteryl octadeca-9,12-dienoate. It has a role as a mouse metabolite and a human metabolite. It is a CE(18:2) and a cholesteryl octadeca-9,12-dienoate. It is functionally related to a linoleic acid.

Names & identifiers

Preferred name: Cholesteryl Linoleate
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] (9Z,12Z)-octadeca-9,12-dienoate
English name: Cholesteryl linoleate
Molecular formula: C45H76O2
Molecular weight: 649.09

Names & synonyms

Cholesteryl linoleateCholesterol Linoleate604-33-1Cholesterol, linoleate18:2 Cholesteryl esterCE(18:2)CE(18:2(9Z,12Z))Cholest-5-en-3beta-yl (Z,Z)-octadeca-9,12-dienoate75427237HI(Z,Z)-(3beta)-Cholest-5-en-3-ol 9,12-octadecadienoateCHEBI:41509cholest-5-en-3beta-yl (9Z,12Z-octadecadienoate)

Show more names

SKL147Cholesteryl linoleic acidCholesterol Linoleate >linoleicacid,cholesterylesterCholesteryl octadecadienoate5-Cholesten-3β-ol 3-linoleateLINOLEIC ACID CHOLESTEROL ESTER

(3beta)-cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoate(3beta)-cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoateNSC-18183[(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] (9Z,12Z)-octadeca-9,12-dienoate((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) (9Z,12Z)-octadeca-9,12-dienoateRefChem:125710cholesteryl trans-9-trans-12-octadecadienoate(17-(1,5-dimethylhexyl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-3-yl) (9Z,12E)-octadeca-9,12-dienoate

Database identifiers

CAS: 604-33-1
PubChem CID: 5287939
ChEBI: CHEBI:41509
UNII: 75427237HI
EC Number: 210-065-9
Nikkaji: J150.304I

Properties

Computed structural properties

XLogP: 15.9
Topological polar surface area: 26.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 21
Heavy atoms: 47
Formal charge: 0
Complexity: 1,020

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Lipids · 2 items

Lipids -> Unambiguous Lipids

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

Collision Cross Section · 3 items

290.8 Å² [M+NH4]+ [CCS Type: DT; Buffer gas: N2; Sample Type: Human plasma; Dataset: Unambiguous Lipids]

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

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

Physicochemical properties

Melting point: 41 · 41-42.5 °C
Boiling point: 677.3 · 677.3±44.0 °C(Predicted)
Density: 0.96 · 0.96±0.1 g/cm3(Predicted)
refractive index: 20 · 〔α〕D20 -24° 14)
Flash point: 113 °C · 113 °C
storage temp.: -20 °C · -20°C
solubility: 10 mg/ml · Chloroform: 10 mg/ml
form: A waxy crystal
color: White to off-white
biological source: synthetic (organic)
InChIKey: NAACPBBQTFFYQB-LJAITQKLSA-N
SMILES: CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@@H]3CC=C2C1)[C@H](C)CCCC(C)C
LogP: 18.17 · 18.170 (est)
CAS DataBase Reference: 604 · 604-33-1(CAS DataBase Reference)
FDA UNII: 75427237 HI · 75427237HI
EPA Substance Registry System: -5 · Cholest-5-en-3-ol (3.beta.)-, (9Z,12Z)-9,12-octadecadienoate (604-33-1)
UNSPSC Code: 12352211 · 12352211
NACRES: 77 · NA.77
PPE: 95 · Eyeshields, Gloves, type N95 (US)
WGK Germany: 3 · 3
TSCA: TSCA listed
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Regulatory InformationCholest-5-en-3-ol (3.beta.)-, (9Z,12Z)-9,12-octadecadienoate: Does not have an individual approval but may be used under an appropriate group standard

Safety data

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

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationCholest-5-en-3-ol (3.beta.)-, 3-[(9Z,12Z)-9,12-octadecadienoate]: INACTIVE

Applications

UsesCholesteryl linoleate was cosonicated with cholesterol to prepare dispersions were prepared to study the cholesterol to phospholipid ratio in red blood cell membrane. It was used as HPLC standard in the analysis of rat liver lipoproteins.

Suppliers57 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]

上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]

Additional notes

DefinitionChEBI: The (9Z,12Z)-stereoisomer of cholesteryl octadeca-9,12-dienoate.

Related reactions

2 records

New reaction record

HRID 441704As reactantuspto-grants-1977_08

HRID 1752828As productuspto-grants-2015_10

Compound notes

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