7448-02-4

Basic information

• Product Name: 4,4-dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol
• Synonyms: 4,4-dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol;30-Nor-8,24-lanostadiene-3β-ol;30-Norlanosta-8,24-dien-3β-ol;30-Norlanosterol;4,4-Dimethyl-5α-cholesta-8,24-dien-3β-ol;4,4-Dimethylzymosterol;Norlanosterol;Cholesta-8,24-dien-3-ol,4,4-diMethyl-, (3b,5a)-
• CAS NO: 7448-02-4
• Molecular Formula: C29H48O
• Molecular Weight: 412.69
• Mol File: 7448-02-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 495.1°C at 760 mmHg
• Flash Point: 217.6°C
• Appearance: /
• Density: 0.99g/cm³
• Vapor Pressure: 7.07E-12mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: -70°C
• CAS DataBase Reference: 4,4-dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol(7448-02-4)
• EPA Substance Registry System: 4,4-dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol(7448-02-4)

Safety Data

• Hazardous Substances Data: 7448-02-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 7448-02-4 differently. You can refer to the following data:
1. 14-Norlanosterol, is a metabolite of Lanosterol (L174580). It is also a meiosis activating sterol (MAS), which is shown to have an important role in regulating meiosis and reproduction.
2. 14-demethyl-lanosterol has been used to reduce cancer cell viability and increase cancer cell sensitivity to erlotinib.

Definition

ChEBI: A 3beta-sterol formed formally by loss of a methyl group from the 14-position of lanosterol.

General Description

14-demethyl-lanosterol acts as an intermediate in cholesterol biosynthesis. It is used to stimulate oocytes for meiosis. 14-demethyl-lanosterol modulates cumulus expansion.

InChI:InChI=1/C29H48O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,20,22-23,25-26,30H,8,10-18H2,1-7H3/t20-,22-,23+,25+,26+,28-,29-/m1/s1

Upstream product

• 79-63-0 tirucallol 
• 674-26-0 mevalonolactone 
• 7408-47-1 4,4-Dimethylzymosterol benzoate 
• 563-80-4 3-methyl-butan-2-one 
• 117438-93-4 (3β,5α,20S)-3-(Benzoyloxy)-4,4-dimethyl-15-oxopregn-8,14-ene-20-carboxaldehyde 
• 209850-50-0 3β-(Benzoyloxy)-24-hydroxy-4,4-dimethyl-5α-cholest-8(14)-ene-15-one 
• 103751-19-5 (3β,5α,22E)-3-(benzoyloxy)-4,4-dimethylergosta-8(14),22-dien-15-one 
• 117439-18-6 Benzoic acid (3S,5R,10S,13R,14R,17R)-17-((R)-4-hydroxy-1,5-dimethyl-hexyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 117438-97-8 3β-(Benzoyloxy)-4,4-dimethyl-5α-cholest-8(14)-ene-15,24-dione 
• 117438-96-7 Benzoic acid (3S,5R,9R,10R,13R,17R)-17-((E)-(R)-1,5-dimethyl-4-oxo-hex-2-enyl)-4,4,10,13-tetramethyl-15-oxo-2,3,4,5,6,7,9,10,11,12,13,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 209850-48-6 Benzoic acid (3S,5R,9R,10R,13R,17R)-17-((S)-2-hydroxy-1,5-dimethyl-4-oxo-hexyl)-4,4,10,13-tetramethyl-15-oxo-2,3,4,5,6,7,9,10,11,12,13,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 117439-14-2 Benzoic acid (3S,5R,10S,13R,14R,15S,17R)-17-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-hexyl]-15-hydroxy-4,4,10,13-tetramethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 117439-16-4 Benzoic acid (3S,5R,10S,13R,14R,17R)-17-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-hexyl]-4,4,10,13-tetramethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 117439-09-5 Benzoic acid (3S,5R,10S,13R,17R)-17-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-hexyl]-4,4,10,13-tetramethyl-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 

Downstream Products

• 5241-24-7 4,4-dimethyl-5α-cholesta-8-en-3β-ol 
• 55429-93-1 [(3S,5R,10S,13R,14R,17R)-17-((R)-1,5-Dimethyl-hex-4-enyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-trimethyl-silane 

Relevant articles and documents

Biosynthetic preparation of labeled 4,4-dimethylzymosterol

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Synthesis of zymosterol, fecosterol, and related biosynthetic sterol intermediates

The first syntheses of sterol biosynthetic intermediates zymosterol(4), 4,4-dimethylzymosterol(5), cholesta-8,14,24-trien-3β-ol(6), the 4,4-dimethyl analogue 7, and fecosterol (8) are described in detail. Multigram quantities of key intermediates 16 and 17 were efficiently prepared from known enones 20 and 21 (eight steps, 35% overall yield). Novel entry into Δ8-sterols was achieved through regiospecific hydroboration/deoxygenation of the 8,14-diene systems. Sterols containing Δ24- or Δ(24(28))-olefins were obtained from C24-hydroxy intermediates either via dehydration using bis[α,α-bis(trifluoromethyl)benzenemethanolato]diphenylsulfur in CH2Cl2 or via Swern oxidation/Wittig olefination, respectively. In this way, 16 and 17 were converted to the desired Δ8,24-, Δ8,14,24-, and Δ(8,24(28))-sterols with high regiocontrol.