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

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

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 
• 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 
• 604-35-3 Cholesteryl acetate 
• 601-57-0 Cholest-4-en-3-one 
• 57-88-5 cholesterol 
• 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 
• 3464-61-7 6,β-bromo-4-cholesten-3-one 
• 3464-58-2 2α,6β-Dibromcholest-4-en-3-on 

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 
• 17605-79-7 3-hydroxy-1-methyl-19-norcholesta-1,3,5(10)-triene 
• 1450594-34-9 C₃₃H₄₆N₄O₄ 
• 57637-86-2 5α,8α-(4-phenyl-1,2-urazolo)-6-cholesten-3β-ol 
• 57102-18-8 5α,8α-(4-phenyl-1,2-urazolo)-1,6-cholestadien-3β-ol 
• 1182005-25-9 (1,2,5,6-2H4)-7-cholesten-3β-ol 

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.

Method for preparing cholest-1,4,6-triene-3-ketone

The invention provides a method for preparing cholest-1,4,6-triene-3-ketone, and belongs to steroid preparation methods. The method comprises the following steps: adding cholesterol serving as a raw material with liquid bromine; and performing pypocholoride/TEMPO/alkali metal bromide system oxidation, dehydrobromination, carbonyl alpha bromization and secondary dehydrobromination totally five steps to obtain the cholest-1,4,6-triene-3-ketone. The method has remarkable advantages of 1, good reaction selectivity, high yield in each step and mild reaction conditions; and 2, low production cost and simple operation, DDQ and other toxic and harmful reagent pollution prevention and 'Three Wastes' cost reduction.

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.

A novel strategy for the synthesis of bromo-substituted cholestenone and its new application to a synthesis of 1α-hydroxycholesterol

A novel and efficient method was developed for the preparation of bromo-substituted cholestenone, including 6β-bromocholestenone and 2α,6β-dibromocholestenone. The key step in this synthesis is a very mild method for the transformation of 5α,6β-dibromocholesterol into the 6β-bromocholestenone by treatment with NaClO/NaBr/TEMPO, followed by dehydro-bromination with Et3N. Bromination at C-2 with NBS/BPO (benzoyl peroxide) gave the 2α,6β-dibromo cholestenone. This was used in a synthesis of 1α-hydroxycholesterol.

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.

Recoverable Pd/C catalyst mediated dehydrogenation of sterols and an improved synthesis of 1α-hydroxydehydroepiandrosterone

A novel recyclable Pd/C catalyst mediated dehydrogenation of sterols is developed. The conversion of sterols to 1,4,6-trien-3-ones is best achieved with Pd/C as a catalyst (10%) in the presence of six equivalents of allyl diethyl phosphate (ADP) and excess amount of sodium carbonate in DMF under vigorous reflux conditions. This transformation gives 17,17-ethylenedioxyandrost-1,4,6- trien-3-one in better yield than that of DDQ oxidation and thus provides an improved synthesis of 1α-hydroxydehydroepiandrosterone from DHEA.

Chemoselective reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by various hydride reagents

The chemoselectivity of rigid cyclic α,β-unsaturated carbonyl group on the reducing agents was influenced by the ring size and steric factor. Cholesterol (cholest-5-en-3β-ol) and dehydroepiandrosterone (DHEA) were oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione. They were reduced with NaBH4, lithium tri-sec-butylborohydride (l-Selectride), LiAlH4, 9-borabicyclo[3.3.1]nonane (9-BBN), lithium triethylborohydride (Super-hydride), and BH3·(CH3)2S in various conditions, respectively. Reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by NaBH4 (4 equiv.) produced 4,6-cholestadien-3β-ol and 4,6-androstadiene-3β,17β-diol, respectively. Reduction by l-Selectride (12 equiv.) afforded 4,6-cholestadien-3α-ol and 4,6-androstadiene-3α,17β-diol, chemoselectively. Reaction with Super-hydride (12 equiv.) produced 4,6-cholestadien-3-one and 3-oxo-4,6-androstadien-17β-ol. Reduction of 1,4,6-cholestatrien-3-one by 9-BBN (14 equiv.) produced 1,4,6-cholestatrien-3α-ol, but 1,4,6-androstatriene-3,17-dione was not reacted with 9-BBN in the reaction conditions. Reaction of LiAlH4 (6 equiv.) formed 4,6-cholestadien-3β-ol and 3-oxo-1,4,6-androstatrien-17β-ol. Reduction of 1,4,6-cholestatrien-3-one by BH3·(CH3)2S (11 equiv.) gave cholestane as major compound and unlike reactivity of cholesterol, 1,4,6-androstatriene-3,17-dione by 8 equiv. of BH3·(CH3)2S formed 3-oxo-1,4,6-androstatrien-17β-ol. LiAlH4 and BH3·(CH3)2S showed relatively low chemoselectivity.

Synthesis and evaluation of new 6-hydroximinosteroid analogs as cytotoxic agents

Taking into account the structural requirements for cytotoxicity, several new hydroximinosteroid derivatives have been prepared and evaluated for their cytotoxic activity against A-549, H116, PSN1, and T98G cultured tumor cell lines in order to obtain further information on the potential pharmacophoric core of this type of compound. The influence of the oxygenated position in the A ring, the presence of an additional oxygenated position at C-7 and C-16, and a fluorinated position at C-5 were considered in order to study the structure-activity relationships. The results reveal the importance of oxygenated positions in the A ring (e.g., 4,5-epoxide showed an IC50 value against HCT-116 under micromolar level) for an increase in cytotoxic activity in this type of compound. Furthermore, they showed an important selectivity toward colon tumor line (HCT-116).

Epoxidation and reduction of cholesterol, 1,4,6-cholestatrien-3-one and 4,6-cholestadien-3β-ol

Many naturally occurring polyhydroxylated sterols and oxysterols exhibit potent biologic activities. This paper describes reagent and position selectivity of epoxidation and reduction of cholesterol derivatives. Cholesterol was reacted with m-chloroperoxybenzoic acid (m-CPBA) to form 5α,6α-epoxycholestan-3β-ol, but in reaction with 30% H 2O2, it did not reacted. 1,4,6-Cholestatrien-3-one was obtained from cholesterol and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in dioxane. 1,4,6-Cholestatrien-3-one was reacted with 30% H2O 2 and 5% NaOH in methanol to give 1α,2α-epoxy-4,6- cholestadien-3-one, which was stereoselectively reduced with NaBH4 to form 1α,2α-epoxy-4,6-cholestadien-3β-ol and reduced with Li metal in absolute ethanol to give 2-ethoxy-1,4,6-cholestatrien-3-one. And 1,4,6-cholestatrien-3-one was epoxidized with m-CPBA in dichloromethane to afford 6α,7α-epoxy-1,4-cholestadien-3-one, which was reacted with NaBH4 to synthesize 6α-hydroxy-4-cholesten-3-one and reduced Li metal in absolute ethanol to form 2-ethoxy-1,4,6-cholestatrien-3-one, respectively. 1,4,6-Cholestatrien-3-one was reduced with NaBH4 in absolute ethanol to form 4,6-cholestadien-3β-ol, which was reacted with 30% H2O2 to leave original compound, but was reacted with m-CPBA to give 4β,5β-epoxy-6-cholesten-3β-ol as the major product and 4β,5β-epoxy-6α,7α-epoxycholestan-3β-ol as the minor product.