516-79-0

Basic information

• Product Name: 22,23-dihydroergosterol, non-irradiated
• Synonyms: 22,23-dihydroergosterol, non-irradiated;22,23-dihydroergosterol;(24S)-Ergosta-5,7-diene-3β-ol;Ergosta-5,7-dien-3β-ol;Provitamin D4;Δ5,7-Ergostadienol;10,13-dimethyl-17-(1,4,5-trimethylhexyl)-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol;17-(5,6-dimethylheptan-2-yl)-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS NO: 516-79-0
• Molecular Formula: C₂₈H₄₆O
• Molecular Weight: 398.66
• EINECS: 208-226-3
• Product Categories: Steroids
• Mol File: 516-79-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 173-174 °C
• Boiling Point: 502.1°Cat760mmHg
• Flash Point: 217.2°C
• Appearance: /
• Density: 0.99g/cm³
• Vapor Pressure: 3.48E-12mmHg at 25°C
• Refractive Index: 1.532
• PKA: 14.91±0.70(Predicted)
• CAS DataBase Reference: 22,23-dihydroergosterol, non-irradiated(CAS DataBase Reference)
• NIST Chemistry Reference: 22,23-dihydroergosterol, non-irradiated(516-79-0)
• EPA Substance Registry System: 22,23-dihydroergosterol, non-irradiated(516-79-0)

Safety Data

• Hazardous Substances Data: 516-79-0(Hazardous Substances Data)

Usage

Definition

ChEBI: A phytosterol consiting of ergostane having double bonds at the 5,6- and 7,8-positions as well as a 3beta-hydroxy group.

InChI:InChI=1/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9-10,18-20,22,24-26,29H,7-8,11-17H2,1-6H3

Upstream product

• 20304-51-2 (24S)-ergosta-5,7-diene-3β-ol 
• 71-43-2 benzene 
• 248580-58-7 3β-tert-butyldimethylsilyloxyergosta-5,7,22-triene-5α,8α-(1,4-dioxo-1,2,3,4-tetrahydrophthalazine-2,3-diyl)ergosta-6,22-diene 
• 2579-14-8 ergostadien-(5,7)-yl-(3β)-acetate 

Downstream Products

• 516-78-9 (3β,5α)-ergost-7-en-3-ol 
• 516-79-0 lumistadien-(5,7)-ol-(3β) 
• 511-28-4 2,2-dihydroergocalciferol 
• 632-32-6 (3β,5α)-ergost-8(14)-en-3-ol 
• 6034-34-0 O-(3.5-dinitro-benzoyl)-fungisterol 
• 6034-33-9 O-benzoyl-fungisterol 
• 120176-30-9 suprasterol4 
• 37706-52-8 previtamin D₄ 
• 511-28-4 vitamin D₄ 
• 122276-71-5 toxisterol D 
• 122293-10-1 toxisterol F 
• 37706-52-8 previtamin D₄ 
• 511-28-4 vitamin D₄ 
• 122276-72-6 toxisterol A 

Relevant articles and documents

Effect of sterol side chain on ion channel formation by amphotericin b in lipid bilayers

Amphotericin B (AmB) is one of the most efficient antimycotic drugs used in clinical practice. AmB interacts with membrane sterols increasing permeability of fungal membranes; however, it is still unclear how AmB selectively recognizes the fungal sterol, ergosterol (Erg), over other sterols in cell membranes. In this study, we investigated the effect of an Erg side chain on AmB activity by testing a series of Erg analogues that shared the same alicyclic structure as Erg but varied in the side chain structure by using the K+ influx assay. The results clearly showed that the sterol side chain is essential for AmB selectivity toward Erg and for the activity of AmB-sterol ion channels. In agreement with our previous findings showing the direct interaction between the drug and Erg, these data suggested that AmB directly recognizes the sterol side chain structure, consequently promoting the formation of ion channels by AmB. Furthermore, the C24 methyl group and Δ22 double bond in the side chain of Erg are equally important for the interaction with AmB. Conformational analysis revealed that the C24 methyl group contributes to the interaction by increasing the van der Waals (VDW) contact area of the side chain, while the Δ22 double bond restricts the side chain conformation to maximize the VDW contact with the rigid AmB aglycone. This study provides direct experimental evidence of the mechanism of AmB selectivity toward fungal Erg.

Method of inhibiting the hyperproliferation of malignant cells

1α-hydroxy vitamin D4 and analogues, preferably 1,24 dihydroxy vitamin D4, which are useful as active compounds of pharmaceutical compositions for the inhibition of hyperproliferative activity of malignant cells.