Cholesteryl oleyl carbonate - ≥98% , CAS No.17110-51-9

CAS: 17110-51-9 Cat. No.: C132281 Molecular Weight: 681.14 EC Number: 241-179-7

GRADE & PURITY ≥98%

Synonyms

CHOLESTERYL OLEYL CARBONATE [INCI] | DTXSID70889389 | CARBONIC ACID, CHOLESTERYL 9-OCTADECENYL ESTER, (Z)- | Cholest-5-en-3-ol (3.beta.)-, (9Z)-9-octadecenyl carbonate | Cholesterol Oleyl Carbonate | Cholest-5-en-3beta-yl (Z)-octadec-9-en-1-yl carbonate |

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Cholesteryl oleyl carbonate(COC) is a carbonate ester of cholesterol and oleyl alcohol with carbonic acid that is used as a liquid crystal(LC) molecule. It has is a crystalline material with a helical structure

A esterified cholesterol derivative with liquid crystal applications.

COC can be incorporated in the polyethylene glycol(PEG)-polyurethane(PU) matrix that exhibits lower thrombogenicity and an improved haemocompatibility which can used as a biomaterial in biomedical applications. It may also be self-assembled with cadmium selenide(CdSe) quantum dots(QDs) for the fabrication of novel multifunctional switchable devices

Specifications

Synonyms

CHOLESTERYL OLEYL CARBONATE [INCI] | DTXSID70889389 | CARBONIC ACID, CHOLESTERYL 9-OCTADECENYL ESTER, (Z)- | Cholest-5-en-3-ol (3.beta.)-, (9Z)-9-octadecenyl carbonate | Cholesterol Oleyl Carbonate | Cholest-5-en-3beta-yl (Z)-octadec-9-en-1-yl carbonate |

Specifications & Purity

≥98%

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488195720
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488195720
• Canonical Smiles: CCCCCCCC\C=C/CCCCCCCCOC(=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
• 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] [(Z)-octadec-9-enyl] carbonate
• InChIKey: XMPIMLRYNVGZIA-TZOMHRFMSA-N
• INCHI: 1S/C46H80O3/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-34-48-44(47)49-39-30-32-45(5)38(35-39)26-27-40-42-29-28-41(37(4)25-23-24-36(2)3)46(42,6)33-31-43(40)45/h14-15,26,36-37,39-43H,7-13,16-25,27-35H2,1-6H3/b15-14-/t37-,39+,40+,41-,42+,43+,45+,46-/m1/s1
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCCOC(=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
• Molecular Weight: 681.14
• Reaxy-Rn: 2068799
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2068799&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Cholestane steroids
• Intermediate Tree Nodes: Not available
• Direct Parent: Cholesterols and derivatives
• Alternative Parents: Delta-5-steroids Carbonic acid diesters Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Cholesterol - Delta-5-steroid - Carbonic acid diester - Carbonic 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 cholesterols and derivatives. These are compounds containing a 3-hydroxylated cholestane core.
• External Descriptors: Not available

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

• Specific Rotation[α]: [α]D：-23° (C=2,CHCl3)
• Molecular Weight: 681.100 g/mol
• XLogP3: 17.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 24
• Exact Mass: 680.611 Da
• Monoisotopic Mass: 680.611 Da
• Topological Polar Surface Area: 35.500 Ų
• Heavy Atom Count: 49
• Formal Charge: 0
• Complexity: 1010.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Fang Li, Nuotong Shen, Limin Zhang, Chen Yang, Zijun Ma, Junhao Gao, Bing Li, Fengshan Shen, Weijun Kong.  (2025)  Skin-Conformal Multifunctional Microfluidic Colorimetric Detection Device for Multiplexed Sweat Analysis.  ACS Sensors,      [PMID:40746283] [10.1021/acssensors.5c01354]