cholesteryl linoleate - ≥95%, used for Cholesteryl 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 r

CAS: 604-33-1 Cat. No.: C136957 Molecular Weight: 649.1

GRADE & PURITY ≥95%

Synonyms

3(beta)-Hydroxy-5-cholestene 3-linoleate | (3beta)-cholest-5-en-3-yl (9Z,12Z)-octadeca-9,12-dienoate | cholesteryl (9Z,12Z)-octadecadienoate | W-105253 | DB02092 | 18:2 Cholesteryl ester | (3beta)-cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoate | (Z,Z)-(3b

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

3(beta)-Hydroxy-5-cholestene 3-linoleate | (3beta)-cholest-5-en-3-yl (9Z,12Z)-octadeca-9,12-dienoate | cholesteryl (9Z,12Z)-octadecadienoate | W-105253 | DB02092 | 18:2 Cholesteryl ester | (3beta)-cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoate | (Z,Z)-(3b

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

Cholesteryl linoleate is a major cholesterol ester found associated with the neutral core of low density lipoprotein. Receptor-LDL complexes are taken up by lysosomes and hydrolyzed to release cholesterol from the esters. The enzyme acid cholesteryl ester

Application

Cholesteryl 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.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 504763511
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763511
• Canonical Smiles: CCCCCC=CCC=CCCCCCCCC(=O)OC1CCC2(C3CCC4(C(C3CC=C2C1)CCC4C(C)CCCC(C)C)C)C
• IUPAC Name: [(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
• InChIKey: NAACPBBQTFFYQB-LJAITQKLSA-N
• INCHI: 1S/C45H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h11-12,14-15,26,35-36,38-42H,7-10,13,16-25,27-34H2,1-6H3/b12-11-,15-14-/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1
• Isomeric SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CC=C2C1)CC[C@@H]4[C@H](C)CCCC(C)C)C)C
• WGK Germany: 3
• Alternate CAS: 70190-89-5
• Molecular Weight: 649.1
• Reaxy-Rn: 2343142
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2343142&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Steroid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Steroid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Cholesteryl esters
• Alternative Parents: Cholesterols and derivatives Delta-5-steroids Lineolic acids and derivatives Carboxylic acid esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Cholesteryl ester - Cholesterol - Cholestane-skeleton - Delta-5-steroid - Octadecanoid - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cholesteryl esters. These are compounds containing an esterified cholestane moiety.
• External Descriptors: Steryl esters

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Flash Point(°F): >235.4 °F
• Flash Point(°C): >113 °C
• Molecular Weight: 649.100 g/mol
• XLogP3: 15.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 21
• Exact Mass: 648.585 Da
• Monoisotopic Mass: 648.585 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 47
• Formal Charge: 0
• Complexity: 1020.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1

References

1. Qiong Wu, Jing Yu, Mingjin Zhang, Yinran Xiong, Lijia Zhu, Bo Wei, Ting Wu, Yiping Du.  (2023)  Serum lipidomic profiling for liver cancer screening using surface-assisted laser desorption ionization MS and machine learning.  TALANTA,      [PMID:37931569] [10.1016/j.talanta.2023.125371]