11-cis-Retinol - Moligand™, ≥85% , CAS No.22737-96-8

CAS: 22737-96-8 Cat. No.: C335449 Molecular Weight: 286.45

GRADE & PURITY Moligand™, ≥85%

Synonyms

11-cis-Retinol | (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol | CHEBI:16302 | 11-cis-Vitamin A alcohol | Q27070756 | 11Z-retinol | 11-cis-13,14-Dihydro Retinol | C00899 | (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimet

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

11-cis-Retinol is a metabolite of Vitamin A. Retinol and derivatives of retinol such as 11-cis-Retinol play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response.11-cis-retinol is produced from vitamin A cycles driven by interphotoreceptor retinoid binding proteins. 11-cis-retinol is also released from retinal pigment epithelium(RPE) membranes. 11-cis-Retinol is also known as cis-11-Retinol, 11-cis-Vitamin A Alcohol, (11cis,13cis)-Retinol, 11Z-retinol, and (2Z,4Z,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol.

Specifications

Synonyms

11-cis-Retinol | (2E, 4Z, 6E, 8E)-3, 7-dimethyl-9-(2, 6, 6-trimethylcyclohexen-1-yl)nona-2, 4, 6, 8-tetraen-1-ol | CHEBI:16302 | 11-cis-Vitamin A alcohol | Q27070756 | 11Z-retinol | 11-cis-13, 14-Dihydro Retinol | C00899 | (2E, 4Z, 6E, 8E)-3, 7-dimethyl-9-(2, 6, 6-trimet

Specifications & Purity

Moligand™, ≥85%

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Grade

Moligand™

Purity

≥85%

Names and Identifiers

• Canonical Smiles: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CCO)C)C
• IUPAC Name: (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol
• InChIKey: FPIPGXGPPPQFEQ-IOUUIBBYSA-N
• INCHI: 1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6-,12-11+,16-8+,17-13+
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C\C(=C\CO)\C)/C
• Molecular Weight: 286.45
• Reaxy-Rn: 1913942
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1913942&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Retinoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Retinoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Retinoids
• Alternative Parents: Diterpenoids Fatty alcohols Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Retinoid skeleton - Diterpenoid - Fatty alcohol - Fatty acyl - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aliphatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
• External Descriptors: Retinoids

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

• Molecular Weight: 286.500 g/mol
• XLogP3: 5.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 286.23 Da
• Monoisotopic Mass: 286.23 Da
• Topological Polar Surface Area: 20.200 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 496.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 4
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 4
• Covalently-Bonded Unit Count: 1

References

1. Jianming Liu, Na Yang, Xingcheng Yi, Guoqiang Wang, Cuizhu Wang, Hongqiang Lin, Liwei Sun, Fang Wang, Dongdong Zhu.  (2023)  Integration of transcriptomics and metabolomics to reveal the effect of ginsenoside Rg3 on allergic rhinitis in mice.  Food & Function,  14  (5): (2416-2431).  [PMID:36786409] [10.1039/D2FO03885D]