3464-60-6

Basic information

• Product Name: cholesta-1,4,6-trien-3-one
• Synonyms: cholesta-1,4,6-trien-3-one;Einecs 222-416-3
• CAS NO: 3464-60-6
• Molecular Formula: C₂₇H₄₀O
• Molecular Weight: 380.6059
• EINECS: 222-416-3
• Mol File: 3464-60-6.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 495.1°Cat760mmHg
• Flash Point: 209.8°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 6.1E-10mmHg at 25°C
• Refractive Index: 1.54
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: cholesta-1,4,6-trien-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: cholesta-1,4,6-trien-3-one(3464-60-6)
• EPA Substance Registry System: cholesta-1,4,6-trien-3-one(3464-60-6)

Safety Data

• Hazardous Substances Data: 3464-60-6(Hazardous Substances Data)

Usage

Description

Cholesta-1,4,6-trien-3-one is an organic compound that serves as an intermediate in the synthesis of various cholesterol and cholestane derivatives. It is characterized by its unique chemical structure, featuring three double bonds at positions 1, 4, and 6, and a ketone group at position 3. Cholesta-1,4,6-trien-3-one has potential applications in the pharmaceutical and chemical industries due to its ability to act as an anti-inflammatory and antifungal agent.

Uses

1. Used in Pharmaceutical Industry:
Cholesta-1,4,6-trien-3-one is used as an intermediate in the synthesis of (3β)-Cholesta-4,6-dien-3-ol (C292700), a cholesterol (C432501) and cholestane (C431700) derivative. This derivative has the potential to act as an anti-inflammatory and antifungal compound, making it a valuable component in the development of new drugs for treating inflammation and fungal infections.
2. Used in Chemical Industry:
Cholesta-1,4,6-trien-3-one is also utilized as a key intermediate in the chemical industry for the production of various cholesterol and cholestane derivatives. These derivatives find applications in a wide range of fields, including pharmaceuticals, cosmetics, and the synthesis of other bioactive compounds.

InChI:InChI=1/C27H40O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,13,15,17-19,22-25H,6-8,11-12,14,16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

Upstream product

• 108-75-8 2,4,6-trimethyl-pyridine 
• 71-41-0 pentan-1-ol 
• 96177-75-2 2α-bromo-cholesta-4,6-dien-3-one 
• 57-88-5 cholesterol 
• 14214-69-8 cholest-4,6-diene-3-ol 
• 566-93-8 cholesta-4,6-dien-3-one 
• 64313-97-9 2,6-dibromo-4-cholesten-3-one 
• 75981-10-1 cholesta-1,4,6-trien-3-one p-nitrophenylhydrazone 
• 604-35-3 Cholesteryl acetate 
• 61949-57-3 7-α,β-bromocholesteryl 3β-acetate 
• 601-57-0 Cholest-4-en-3-one 
• 84-58-2 2,3-dicyano-5,6-dichloro-p-benzoquinone 
• 28893-44-9 1α,2α-epoxycholesta-1,4,6-trien-3-one 
• 1857-80-3 5α,6β-dibromocholestan-3β-ol 

Downstream Products

• 566-93-8 cholesta-4,6-dien-3-one 
• 28893-44-9 1α,2α-epoxycholesta-1,4,6-trien-3-one 
• 80-97-7 Cholestanol 
• 14214-69-8 cholest-4,6-diene-3-ol 
• 481-20-9 cholestane 
• 434-16-2 7-dehydrocholesterol 
• 6036-58-4 cholest-7-en-3β-ol 
• 1182005-25-9 (1,2,5,6-2H4)-7-cholesten-3β-ol 
• 57102-18-8 5α,8α-(4-phenyl-1,2-urazolo)-1,6-cholestadien-3β-ol 
• 57637-86-2 5α,8α-(4-phenyl-1,2-urazolo)-6-cholesten-3β-ol 
• 17605-79-7 3-hydroxy-1-methyl-19-norcholesta-1,3,5(10)-triene 
• 1450594-34-9 C₃₃H₄₆N₄O₄ 

Relevant articles and documents

Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds

An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.

A new synthetic method of 1β- and 2β-hydroxyprovitamin D3, the precursor of the 1β- and 2β-hydroxyvitamin D3

A new method was described for the synthesis of 1β- and 2β-hydroxyprovitamins D3, the photoprecusors of 1β- and 2β-hydroxyvitamin D3. The key step of stereoselective introduction of C-1 and C-2 hydroxy groups was performed with a very mild method for the hydroxybromination of the D-A cyclo adduct with tribromoisocyanuric acid(TBCA)/water. The newly developed method requires no toxic or expensive reagents and 1β(2β)-hydroxyprovitamin D3 was obtained with excellent yield and stereoselectivity.

Semisynthesis and quantitative structure-activity relationship (QSAR) study of some cholesterol-based hydrazone derivatives as insecticidal agents

In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, four series of novel cholesterol-based hydrazone derivatives were synthesized, and their insecticidal activity was tested against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at 1 mg/mL. All the derivatives showed the better insecticidal activity than their precursor cholesterol. Quantitative structure-activity relationship (QSAR) model demonstrated that six descriptors such as RDF085v, Mor06u, Mor11u, Dv, HATS0v and H-046, are likely to influence the insecticidal activity of these compounds. Among them, two important ones are the Mor06u and RDF085v.