1224-95-9

Basic information

• Product Name: Androstan-3-one
• Synonyms: 3-KETO-5-ALPHA-ANDROSTANE;5-ALPHA-ANDROSTAN-3-ONE;5α-Androstan-3-one;Androstanone;(5S,8S,9S,10S,13S,14S)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS NO: 1224-95-9
• Molecular Formula: C₁₉H₃₀O
• Molecular Weight: 274.44
• Mol File: 1224-95-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 103-104 °C
• Boiling Point: 368.5°Cat760mmHg
• Flash Point: 168.7°C
• Appearance: /
• Density: 1.014
• Vapor Pressure: 1.27E-05mmHg at 25°C
• Refractive Index: 1.517
• CAS DataBase Reference: Androstan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: Androstan-3-one(1224-95-9)
• EPA Substance Registry System: Androstan-3-one(1224-95-9)

Safety Data

• Hazardous Substances Data: 1224-95-9(Hazardous Substances Data)

Usage

General Description

Androstan-3-one, also known as Androsterone, is an endogenous steroid hormone, neurosteroid, and pheromone. It is naturally synthesized from the metabolism of testosterone in human beings, and animals as well. Androsterone was the first neurosteroid to be discovered and was subsequently found to be converted into epiandrosterone. It is less active than testosterone but more active than epi-androsterone, and it may exert inhibitory effects on the central nervous system. It is a crucial compound in the biosynthesis of many other bioactive androgens. Furthermore, Androstan-3-one is also used in the perfume industry due to its inherent scent.

InChI:InChI=1/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h13,15-17H,3-12H2,1-2H3/t13-,15-,16-,17-,18-,19-/m0/s1

Upstream product

• 18339-16-7 5α-androst-16-en-3-one 
• 1224-93-7 5α-androstan-3β-ol 
• 64-19-7 acetic acid 
• 4732-78-9 (3β,5α,13β)-3-hydroxy-18-norandrostan-17-one 
• 1476-64-8 androst-5-en-3β-ol 
• 53-43-0 dehydroepiandrosterone 
• 481-29-8 Epiandrosterone 
• 2872-90-4 4-androsten-3-one 
• 3248-10-0 (5S,8S,9S,10S,13S,14S)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one 
• 65628-29-7 17-semicarbazone of 3β-hydroxyandrost-5-en-17-one 
• 141-52-6 sodium ethanolate 

Downstream Products

• 1434-14-6 3,3-Aethylendioxy-5α-androstan 
• 4642-50-6 5α-Androstan-3-spiro-2'-thiazolidin 
• 69809-13-8 2α-Phenylseleno-5α-androstan-3-on 
• 81916-97-4 androstane-3α-ylmethyl toluene-p-sulphonate 
• 81916-98-5 androstane-3β-ylmethyl toluene-p-sulphonate 
• 25788-17-4 5α-Androstan-12,15-dion 
• 4642-58-4 3--5α-androst-2-en 
• 4642-51-7 3--5α-androst-2-en 
• 4678-96-0 3'-acetyl-(3ξN,5α)-spiro[androstane-3,2'-thiazolidine] 
• 26156-06-9 2-p-Methoxybenzyliden-5α-androstan-3β-ol 
• 25825-89-2 2-p-Methoxybenzyliden-5α-androst-3en 
• 78514-54-2 Benzoic acid (5S,8S,9S,10S,13S,14S)-10,13-dimethyl-3-phenylsulfanylmethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 3090-99-1 3-ketoandrosta-1,4-diene 
• 17287-99-9 2-(4-Methoxybenzyliden)-5α-androstan-3-on 

Relevant articles and documents

METHODS OF ACTIVATING MICROGLIAL CELLS

The present disclosure provides methods of using compositions that inhibit SH2-containing inositol 5'-phosphatases (SHIPs) for activating microglial cells, as well as methods for using such compositions for treatment or ameliorating of neurodegenerative disorders in a subject.

Androstanes with modified carbon skeletons

Four sterane hydrocarbons were prepared for comparisonwith fossil organic biomarkers in geological samples from Oman. 17ss-Methylestrane was prepared in six steps (36% overall yield) from estrone methyl ether. Key steps of this sequence were a Wittig olefination and Birch reduction of the A-ring. 17ss-Methylandrostane was obtained in four steps (85% overall yield) from trans-androsterone by four functional group interconverting reactions, including aWittig olefination. 17ss-Methyl-and 2α-methyl-A-nor-5α- androstanes (14 and 15% overall yields, respectively) were also prepared from trans-androsterone. Key steps were the thallium trinitrate mediated ring contractions of A-ring ketones to A-nor-2-carboxylic acids. Defunctionalization in the four syntheses was achieved by catalytic hydrogenation, Huang-Minlon reduction, Barton decarboxylation, and Bu3SnH-mediated reduction of a chloromethyl group, respectively.

Photochemical Behavior of Δ4-3-Oxo, Δ5-7-Oxo, and Δ1-3-Oxo Steroids in Concentrated Acid Solution

Irradiation with UV light of 5α-androst-1-en-3-one (9) in concentrated sulfuric acid leads to 15 and 16; similarly 4a-methyl-4a,5,6,7,8,8a-hexahydronaphthalen-2(1H)-one (10) gives 17 and 18.The formation of the four products is rationalized in terms of a photochemically induced 1,2-alkyl shift to the positively charged positions of the starting carbenium ions.On the other hand, irradiation under the same conditions of 4, 8, 7, and 11 yields, quantitatively, unchanged starting material, while the analogous bicyclic compound Δ1,9-10-methyl-2-octalone (1) has been reported to yield photorearrangement products.The lack of reactivity of 7 and 11 can be explained according to the proposed mechanism for the photorearrangement of 1.In the case of 4 and 8, the presence of the steroid rings C and D prevents the photorearrangement, but the mechanistic explanation of this effect cannot be determined from the present experimental data.