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

Description

CEREVISTEROL, also known as an ergostanoid, is a metabolite derived from the endophytic fungus Mollisia. It is characterized by its (22E)-ergosta-7,22-diene structure, which is substituted by hydroxy groups at positions 3, 5, and 6 (the 3beta,5alpha,6beta stereoisomer). This unique chemical composition has led to its isolation from the fungus, Xylaria species, and has garnered interest in its potential applications.

Uses

Used in Pharmaceutical Industry:
CEREVISTEROL is used as a pharmaceutical compound for its potential therapeutic properties. Its unique structure and origin from endophytic fungi suggest that it may possess bioactive properties that can be harnessed for the development of new drugs or treatments.
Used in Research and Development:
CEREVISTEROL is used as a research compound for studying its chemical properties, biological activities, and potential applications in various fields. Its isolation from the fungus, Xylaria species, makes it an interesting subject for exploring the relationship between endophytic fungi and their host plants, as well as their potential role in producing bioactive compounds.
Used in Drug Discovery:
CEREVISTEROL is used as a starting material or a lead compound in drug discovery processes. Its unique ergostanoid structure and hydroxy group substitutions may provide a foundation for the development of new drugs with novel mechanisms of action, particularly in the areas of cancer treatment, inflammation, and other diseases where ergostanoids have shown potential.

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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Discoveries and Challenges en Route to Swinhoeisterol A

In this work, a full account of the authors’ synthetic studies is reported that culminated in the first synthesis of 13(14→8),14(8→7)diabeo-steroid swinhoeisterol A as well as the related dankasterones A and B, 13(14→8)abeo-steroids, and periconiastone A, a 13(14→8)abeo-4,14-cyclo-steroid. Experiments are described in detail that provided further insight into the mechanism of the switchable radical framework reconstruction approach. By discussing failed strategies and tactics towards swinhoeisterol A, the successful route that also allowed an access to structurally closely related analogues, such as Δ22-24-epi-swinhoeisterol A, is eventually presented.

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.