20(S)-Hydroxycholesterol (Standard) , CAS No.516-72-3

CAS: 516-72-3 Cat. No.: S1431689 Formula: C₂₇H₄₆O₂ Molecular Weight: 402.65 PubChem CID: 121935

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

20(S)-Hydroxycholesterol (Standard) is the analytical standard of 20(S)-Hydroxycholesterol. This product is intended for research and analytical applications. 20(S)-hydroxyCholesterol (20α-Hydroxycholesterol) is an allosteric activator of the oncoprotein smoothened ( Smo ) that activates the hedgehog (Hh) signaling pathway with an EC 50 of 3 μM in a gene transcription reporter assay using NIH3T3 cells.

Specifications

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.

Action Type

ACTIVATOR

Names and Identifiers

Canonical Smiles

CC(C)CCCC(C)(C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O

IUPAC Name

(3S,8S,9S,10R,13S,14S,17S)-17-[(2S)-2-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

InChIKey

MCKLJFJEQRYRQT-APGJSSKUSA-N

INCHI

1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27-/m0/s1

Isomeric SMILES

CC(C)CCC[C@@](C)([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)O

PubChem CID

121935

Molecular Weight

402.65

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: 3-beta-hydroxysteroids 3-beta-hydroxy delta-5-steroids Delta-5-steroids Tertiary alcohols Secondary alcohols Cyclic alcohols and derivatives Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Cholesterol - Cholesterol-skeleton - 20-hydroxysteroid - 3-beta-hydroxy-delta-5-steroid - Hydroxysteroid - 3-hydroxy-delta-5-steroid - 3-hydroxysteroid - 3-beta-hydroxysteroid - Delta-5-steroid - Tertiary alcohol - Cyclic alcohol - Secondary alcohol - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Alcohol - 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: Cholesterol and derivatives

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

Frequently Asked Questions

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 516-72-3, the molecular formula is C27H46O2, and the molecular weight is 402.65 g/mol. InChIKey MCKLJFJEQRYRQT-APGJSSKUSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.