5β-Cholanic acid-3α,6β,7α-triol - ≥95% , CAS No.2393-58-0

CAS: 2393-58-0 Cat. No.: C336507 Molecular Weight: 408.57

GRADE & PURITY ≥95%

Synonyms

alpha-MCA | 3alpha,6beta,7alpha-Trihydroxy-5beta-cholan-24-oic Acid | CHEBI:81243 | 3a,6b,7a-trihydroxy-5b-Cholanic acid | (3a,5b,6b,7a)-3,6,7-trihydroxy-Cholan-24-oic acid | 5b-Cholanic acid-3a,6b,7a-triol | Q27155185 | DTXSID101316249 | J-015284 | C1764

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

5β-Cholanic acid-3α,6β,7α-triol is a cholesterol used for proteomics research.

Specifications

Synonyms

alpha-MCA | 3alpha, 6beta, 7alpha-Trihydroxy-5beta-cholan-24-oic Acid | CHEBI:81243 | 3a, 6b, 7a-trihydroxy-5b-Cholanic acid | (3a, 5b, 6b, 7a)-3, 6, 7-trihydroxy-Cholan-24-oic acid | 5b-Cholanic acid-3a, 6b, 7a-triol | Q27155185 | DTXSID101316249 | J-015284 | C1764

Specifications & Purity

≥95%

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

• Canonical Smiles: CC(CCC(=O)O)C1CCC2C1(CCC3C2C(C(C4C3(CCC(C4)O)C)O)O)C
• IUPAC Name: (4R)-4-[(3R,5R,6S,7S,8S,9S,10R,13R,14S,17R)-3,6,7-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• InChIKey: DKPMWHFRUGMUKF-GDYCBZMLSA-N
• INCHI: 1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21+,22+,23-,24-/m1/s1
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H]([C@H]([C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
• Molecular Weight: 408.57
• Reaxy-Rn: 3457148
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3457148&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Bile acids, alcohols and derivatives
        • Level5 Hydroxy bile acids, alcohols and derivatives
          • Level6 Trihydroxy bile acids, alcohols and derivatives

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Bile acids, alcohols and derivatives
• Intermediate Tree Nodes: Hydroxy bile acids, alcohols and derivatives
• Direct Parent: Trihydroxy bile acids, alcohols and derivatives
• Alternative Parents: 7-hydroxysteroids 6-hydroxysteroids 3-alpha-hydroxysteroids Secondary alcohols Cyclic alcohols and derivatives Polyols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Trihydroxy bile acid, alcohol, or derivatives - 3-hydroxysteroid - 6-hydroxysteroid - 7-hydroxysteroid - 3-alpha-hydroxysteroid - Hydroxysteroid - Cyclic alcohol - Secondary alcohol - Carboxylic acid derivative - Carboxylic acid - Polyol - Monocarboxylic acid or derivatives - Organic oxide - Alcohol - Organic oxygen compound - Hydrocarbon derivative - Carbonyl group - Organooxygen compound - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
• External Descriptors: C24 bile acids, alcohols, 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

Chemical and Physical Properties

• Solubility: 20mg/mL in ethanol, or in DMSO, 30mg/mL in DMF
• Melt Point(°C): 199-200° C
• Molecular Weight: 408.600 g/mol
• XLogP3: 3.900
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 408.288 Da
• Monoisotopic Mass: 408.288 Da
• Topological Polar Surface Area: 98.000 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 637.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 11
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Wei Xu, Yingying Kong, Tuo Zhang, Zhihua Gong, Wenjun Xiao.  (2022)  L-Theanine regulates lipid metabolism by modulating gut microbiota and bile acid metabolism.  JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE,  103  (3): (1283-1293).  [PMID:36087337] [10.1002/jsfa.12222]