Cholesteryl oleate - ≥85% , CAS No.303-43-5

CAS: 303-43-5 Cat. No.: C113859 Molecular Weight: 651.1 Beilstein Registry Number: 2343071 EC Number: 206-142-1

GRADE & PURITY ≥85%

Synonyms

CHOLESTEROL 3.BETA.-OLEATE | Cholesteryl oleate-9,10-3H | Oleoylcholesterol | CE(18:1(9Z)) | Cholest-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-dode

Storage

Room temperature

Shipped In

Normal

Overview

Cholesteryl oleate is an esterified form cholesterol found in plasma. The liver is a primary source of cholesteryl oleate that enriches the LDL particles when released into plasma. The secretion of lipoproteins enriched with cholesteryl oleate has close correlation with the pathogenesis of coronary artery atherosclerosis.
An esterified form cholesterol found in plasma

Specifications

Synonyms

CHOLESTEROL 3.BETA.-OLEATE | Cholesteryl oleate-9, 10-3H | Oleoylcholesterol | CE(18:1(9Z)) | Cholest-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-dode

Specifications & Purity

≥85%

Storage

Room temperature

Shipped In

Normal

Purity

≥85%

Names and Identifiers

• Pubchem Sid: 504763476
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763476
• Canonical Smiles: CCCCCCCCC=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] (Z)-octadec-9-enoate
• InChIKey: RJECHNNFRHZQKU-RMUVNZEASA-N
• INCHI: 1S/C45H78O2/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/h14-15,26,35-36,38-42H,7-13,16-25,27-34H2,1-6H3/b15-14-/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1
• Isomeric SMILES: CCCCCCCC/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
• Molecular Weight: 651.1
• Beilstein: 2343071
• Reaxy-Rn: 2068609
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2068609&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 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 - 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

Associated Targets(non-human)

Pseudomonas aeruginosa (123386 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Streptococcus mutans (2687 Activities)

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Streptococcus pyogenes (16140 Activities)

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Pichia kudriavzevii (7448 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Candida parapsilosis (8521 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Specific Rotation[α]: -20 ° (C=2, THF)
• Flash Point(°F): 113 °C
• Flash Point(°C): 113°C
• Melt Point(°C): 44-47°C
• Molecular Weight: 651.100 g/mol
• XLogP3: 16.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 22
• Exact Mass: 650.6 Da
• Monoisotopic Mass: 650.6 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 47
• Formal Charge: 0
• Complexity: 976.000
• 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. Zimin Cai, Qin Wang, Jinzhuan Xu, Jia Zhou, Zhaohui Jiang, Di Pan, Yanyan Zhang, Ling Tao, Jianqing Peng, Yi Chen, Xiangchun Shen.  (2022)  Enhanced protective activity of 1,8-cineole on emphysema using hyaluronic acid-coated liposomes via quantitative pulmonary administration in mice.  JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.jddst.2022.103402]

2. Jianqing Peng, Qin Wang, Jia Zhou, Shuli Zhao, Pan Di, Yan Chen, Ling Tao, Qianming Du, Xiangchun Shen, Yi Chen.  (2021)  Targeted Lipid Nanoparticles Encapsulating Dihydroartemisinin and Chloroquine Phosphate for Suppressing the Proliferation and Liver Metastasis of Colorectal Cancer..  Frontiers in Pharmacology,      [PMID:34690764] [10.3389/fphar.2021.720777]

3. Tianze Yu, Xiaoqiang Xu, Yang Liu, Xiaokai Wang, Shi Wu, Zhuoqiong Qiu, Xiaochun Liu, Xiaoyu Pan, Chaoying Gu, Shangshang Wang, Lixin Dong, Wei Li, Xu Yao.  (2024)  Multi-omics signatures reveal genomic and functional heterogeneity of Cutibacterium acnes in normal and diseased skin.  Cell Host & Microbe,      [PMID:38936370] [10.1016/j.chom.2024.06.002]

4. Xiaoshuang Bi, Yaxin Deng, Chenxiao Chu, Mingli Wei, Jiansong Zhao, Jiaqi Zhao, Yuying Wang, Tian Yin, JingXin Gou, Haibing He, Xing Tang, Guofei Li, Yu Zhang.  (2025)  Precision-targeted explosion of biomimetic nanoparticles for the effective treatment of uveal melanoma.  INTERNATIONAL JOURNAL OF PHARMACEUTICS,      [PMID:40164415] [10.1016/j.ijpharm.2025.125543]

5. Li Yang, Xue Xiaoxia, Yu Liuchunyang, Qian Jinxiu, Li Xiaoyu, Tian Meng, Yang Jue, Deng Rongjun, Lu Cheng, Xiao Cheng, Liu Yuanyan.  (2025)  Recombinant high-density lipoprotein targeted delivery of celastrol to promote foam cells lipophagy against early atherosclerosis.  JOURNAL OF NANOBIOTECHNOLOGY,  23  (1): (1-29).  [PMID:40119460] [10.1186/s12951-025-03327-9]