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

Description

4,4-Dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol, also known as 14-Norlanosterol, is a metabolite of Lanosterol (L174580). It is a meiosis activating sterol (MAS) that plays a crucial role in regulating meiosis and reproduction.

Uses

Used in Cancer Treatment:
4,4-Dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol is used as a cancer treatment agent for reducing cancer cell viability and increasing cancer cell sensitivity to erlotinib. It targets the meiosis and reproduction processes in cancer cells, making them more susceptible to the effects of erlotinib and other chemotherapeutic drugs.
Used in Drug Delivery Systems:
In order to enhance the efficacy and bioavailability of 4,4-dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol, various drug delivery systems have been developed. These systems utilize organic and metallic nanoparticles as carriers for the sterol, improving its delivery to cancer cells and overall therapeutic outcomes.

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

• 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 
• 5241-24-7 4,4-dimethyl-5α-cholesta-8-en-3β-ol 

Relevant articles and documents

Biosynthetic preparation of labeled 4,4-dimethylzymosterol

-

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.