115538-84-6

Basic information

• Product Name: 3,7-dihydroxy-5-cholestenoic acid
• Synonyms: 3,7-dihydroxy-5-cholestenoic acid;3beta,7alpha-Dihydroxy-5-cholestenoate
• CAS NO: 115538-84-6
• Molecular Formula: C27H44O4
• Molecular Weight: 432.64
• Mol File: 115538-84-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 588.1°C at 760 mmHg
• Flash Point: 323.5°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 2.8E-16mmHg at 25°C
• Refractive Index: 1.555
• PKA: 4.81±0.21(Predicted)
• CAS DataBase Reference: 3,7-dihydroxy-5-cholestenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,7-dihydroxy-5-cholestenoic acid(115538-84-6)
• EPA Substance Registry System: 3,7-dihydroxy-5-cholestenoic acid(115538-84-6)

Safety Data

• Hazardous Substances Data: 115538-84-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C27H44O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h15-17,19-24,28-29H,5-14H2,1-4H3,(H,30,31)/t16-,17?,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1

Upstream product

• 566-26-7 (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol 
• 57-88-5 cholesterol 

Relevant articles and documents

Additional pathways of sterol metabolism: Evidence from analysis of Cyp27a1?/? mouse brain and plasma

Cytochrome P450 (CYP) 27A1 is a key enzyme in both the acidic and neutral pathways of bile acid biosynthesis accepting cholesterol and ring-hydroxylated sterols as substrates introducing a (25R)26-hydroxy and ultimately a (25R)26-acid group to the sterol side-chain. In human, mutations in the CYP27A1 gene are the cause of the autosomal recessive disease cerebrotendinous xanthomatosis (CTX). Surprisingly, Cyp27a1 knockout mice (Cyp27a1?/?) do not present a CTX phenotype despite generating a similar global pattern of sterols. Using liquid chromatography – mass spectrometry and exploiting a charge-tagging approach for oxysterol analysis we identified over 50 cholesterol metabolites and precursors in the brain and circulation of Cyp27a1?/? mice. Notably, we identified (25R)26,7α- and (25S)26,7α-dihydroxy epimers of oxysterols and cholestenoic acids, indicating the presence of an additional sterol 26-hydroxylase in mouse. Importantly, our analysis also revealed elevated levels of 7α-hydroxycholest-4-en-3-one, which we found increased the number of oculomotor neurons in primary mouse brain cultures. 7α-Hydroxycholest-4-en-3-one is a ligand for the pregnane X receptor (PXR), activation of which is known to up-regulate the expression of CYP3A11, which we confirm has sterol 26-hydroxylase activity. This can explain the formation of (25R)26,7α- and (25S)26,7α-dihydroxy epimers of oxysterols and cholestenoic acids; the acid with the former stereochemistry is a liver X receptor (LXR) ligand that increases the number of oculomotor neurons in primary brain cultures. We hereby suggest that a lack of a motor neuron phenotype in some CTX patients and Cyp27a1?/? mice may involve increased levels of 7α-hydroxycholest-4-en-3-one and activation PXR, as well as increased levels of sterol 26-hydroxylase and the production of neuroprotective sterols capable of activating LXR.