516-37-0

Basic information

• Product Name: CEREVISTEROL
• Synonyms: CEREVISTEROL;(22E)-5α-Ergosta-7,22-diene-3β,5,6β-triol;(22E)-Ergosta-7,22-diene-3β,5α,6β-triol;(22E,24R)-24-Methyl-5α-cholesta-7,22-diene-3β,5,6β-triol;(22E,24R)-5α-Ergosta-7,22-diene-3β,5,6β-triol;(22E,24R)-Ergosta-7,22-diene-3β,5α,6β-triol
• CAS NO: 516-37-0
• Molecular Formula: C₂₈H₄₆O₃
• Molecular Weight: 430.66
• Mol File: 516-37-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: >240 °C
• Boiling Point: 535 °C at 760 mmHg
• Flash Point: 221.2 °C
• Appearance: /
• Density: 1.08 g/cm³
• Vapor Pressure: 1.12E-13mmHg at 25°C
• Refractive Index: 1.556
• PKA: 13.52±0.70(Predicted)
• CAS DataBase Reference: CEREVISTEROL(CAS DataBase Reference)
• NIST Chemistry Reference: CEREVISTEROL(516-37-0)
• EPA Substance Registry System: CEREVISTEROL(516-37-0)

Safety Data

• Hazardous Substances Data: 516-37-0(Hazardous Substances Data)

Usage

Uses

Cerevisterin is a metabolite from endophytic fungus Mollisia.

Definition

ChEBI: An ergostanoid that is (22E)-ergosta-7,22-diene substituted by hydroxy groups at positions 3, 5 and 6 (the 3beta,5alpha,6beta stereoisomer). It has been isolated from the fungus, Xyl ria species.

InChI:InChI=1/C28H46O3/c1-17(2)18(3)7-8-19(4)22-9-10-23-21-15-25(30)28(31)16-20(29)11-14-27(28,6)24(21)12-13-26(22,23)5/h7-8,15,17-20,22-25,29-31H,9-14,16H2,1-6H3/b8-7+

Upstream product

• 481-23-2 (22E)-5α-hydroxyergosta-7,22-dien-6-on-3β-yl acetate 
• 96646-08-1 5,6β-dihydroxy-5α-ergosta-7,22-dien-3β-yl acetate 
• 7001-69-6 (22E,24R)-methylcholesta-6,22-diene-3β,5α,8α-triol 
• 57-87-4 Ergosterol 
• 23637-31-2 5α,6α-epoxy-24(R)-methylcholesta-7,22-dien-3β-ol 

Downstream Products

• 14858-07-2 3β,5α-dihydroxy-(22E,24R)-ergosta-7,22-dien-6-one 
• 38774-65-1 (22E,24R)-5-hydroxy-5α-ergosta-7,22-diene-3,6-dione 

Relevant articles and documents

Oxidation products of ergosterin. 1. Chromatographic separation of oxidation products, isolation of new radiation products of ergosterin under the influence of oxygen

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Synthesis of the Alleged Structures of Fortisterol and Herbarulide and Structural Revision of Herbarulide

The alleged structures of 5,6-epoxy-5,6-secosteroids fortisterol and herbarulide differ only in the stereoconfiguration of C24. Applying insights into the hypothetical biosynthesis of this class of natural products, we devised a short synthetic access (four and eight steps, respectively) starting from commercial ergosterol and featuring an alkoxy radical rearrangement. The comparison of nuclear magnetic resonance spectroscopic data revealed herbarulide having the proposed structure of fortisterol, whereas synthesis of another two diastereomers could not conclusively prove the true structure of fortisterol. Along the way, a high-yielding and scalable access to the infamous Burawoy's ketone not requiring chromium(VI) reagents was developed.

Synthesis and bioevaluation of Δ7-5-desaturase inhibitors, an enzyme late in the biosynthesis of the fungal sterol ergosterol

Ergosterol, the predominant sterol of fungi, is postulated to have many cellular functions which include a bulk membrane role and a regulatory role. Studies with sterol auxotrophs show that, even in the presence of sterols which can fulfill the bulk membrane requirements, a small concentration of ergosterol is absolutely necessary for growth. The Δ5-double bond appears to be required for the regulatory role of ergosterol; therefore, development of inhibitors of the enzyme that introduce this double bond, Δ7-sterol 5- desaturase (5-desaturase), may lead to effective antifungal agents. Within is the first reported synthesis of inhibitors of fungal 5-desaturase and the development of an in vitro tritium efficacy radioassay. The inhibitors were of the general structure 7,22(E)-ergostadien-3β-ol with α-face heteroatom substituents in the vicinity of C-5. They exhibited IC50 values of 47-149 μM.