1169-20-6

Basic information

• Product Name: 3-Acetyloxypregn-16-en-20-one
• Synonyms: 3-hydroxy-16-pregnene-20-one-3-acetate;(17-acetyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl) acetate;(3b,5b)-3-(Acetyloxy)pregn-16-en-20-one;3-Acetyloxypregn-16-en-20-one;3β-Hydroxypregn-16-en-20-one-3-acetate
• CAS NO: 1169-20-6
• Molecular Formula: C₂₃H₃₄O₃
• Molecular Weight: 358.51
• Mol File: 1169-20-6.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 454.7°Cat760mmHg
• Flash Point: 195.1°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 1.86E-08mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: 3-Acetyloxypregn-16-en-20-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Acetyloxypregn-16-en-20-one(1169-20-6)
• EPA Substance Registry System: 3-Acetyloxypregn-16-en-20-one(1169-20-6)

Safety Data

• Hazardous Substances Data: 1169-20-6(Hazardous Substances Data)

Usage

Uses

(3β,5α)-3-(Acetyloxy)-pregn-16-en-20-one is a Tigogenin derivative used in the synthesis of polyhydroxy steroids; Also, it is an intermediate used in the synthesis of Allopregnenolone (A547105), which acts as a GABAA receptor positive allosteric modulator. It is a metabolite of Progesterone (P755900). s It is also a neuroactive steroid present in the blood and also the brain.

InChI:InChI=1/C23H34O3/c1-14(24)19-7-8-20-18-6-5-16-13-17(26-15(2)25)9-11-22(16,3)21(18)10-12-23(19,20)4/h7,16-18,20-21H,5-6,8-13H2,1-4H3/t16?,17?,18-,20-,21-,22-,23+/m0/s1

Upstream product

• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 2857-74-1 (2aS,4S,6aS,6bS,8aS,8bS,11aS,12aS,12bR)-10-((S)-4-acetamido-3-methylbutyl)-6a,8a,9-trimethyl-2,2a,3,4,5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-hexadecahydro-1H-naphtho[2’,1’:4,5]indeno[2,1-b]furan-4-yl acetate 
• 2066-51-5 16α,17α-epoxypregnan-20-one-3β-ol 3-acetate 
• 108322-64-1 (25R)-3β,26-diacetoxy-5α-furost-22ξ-ene 
• 209979-66-8 17α,21-dichloro-3β-acetoxy-5α-pregnan-20-one 
• 77-60-1 tigogenin 
• 1778-02-5 Pregnenolone acetate 
• 906-83-2 pregnenolone acetate 
• 209979-67-9 3β-acetoxy-5α,6β,17α,21-tetrachloro-20-oxopregnane 
• 28507-81-5 C₂₅H₃₈O₄ 

Downstream Products

• 1044-90-2 (3β,5α,16α)-16,17-epoxy-3-hydroxypregnan-20-one 
• 3090-70-8 (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 
• 571-20-0 5-androgen-3,17-diol 
• 1239-31-2 3β-acetoxy-5α-androstan-17-one 
• 38393-04-3 3α-Hydroxy-5α-pregna-9(11),16-dien-20-one 
• 115040-07-8 3α-Hydroxy-5α-pregn-16-en-20-one 3-m-iodobenzoate 
• 481-29-8 Epiandrosterone 
• 570-59-2 4,5α-dihydro-17α-hydroxyprogesterone 
• 5456-44-0 3β-acetoxy-17-hydroxy-5α-pregnan-20-one 
• 2220-64-6 5α-Pregnan-3β,16α,20α-triol 
• 565-99-1 UC₁₀₁₇ 
• 516-55-2 isopregnanolone 

Relevant articles and documents

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Sisal saponin by a single synthesis method for the production of alcohol ketone acetic ester

The invention relates to a production method for synthesizing pregnenolone acetate with ticogenin, which comprises the following steps: by using ticogenin as a raw material, acetic acid as a solvent and acetic anhydride as an acylating agent, carrying out pressurized ring-opening reaction, and carrying out oxydrolysis with chromic anhydride to obtain a compound reaction solution; extracting, washing with alkali, washing with water, filtering, concentrating under reduced pressure, crystallizing, and centrifuging to obtain a pregnenolone acetate crude product; and finally, recrystallizing to obtain the pregnenolone acetate. The method provided by the invention has the advantages of proper reaction conditions, high total yield, high product purity and low production cost, and is suitable for industrial production.

A practical solution for aqueous reactions of water-insoluble high-melting-point organic substrates

A practical solution to the problem of performing aqueous reactions for very sparingly soluble high-melting-point (VSSHMP) organic substrates has been developed, which entails mechanically stirring a mixture of the substrate, the corresponding reagent(s), water, catalytic Aliquat 336 and sand. When the melting points of the substrates which include steroids, ketones, aldehydes, aromatics and alkaloids are around 200 °C, the reactions can be performed at 20 °C. The substrate solubility can be as low as 1 × 10-10 mol L-1. The Royal Society of Chemistry 2012.

Further study on synthesis and evaluation of 3,16,20-polyoxygenated steroids of marine origin and their analogs as potent cytotoxic agents

A series of new polyoxygenated steroid derivatives with various steroid skeleton moieties were synthesized. Antitumor activity of the compounds against three tumor cell lines (Breast cancer MCF7, lung cancer NCI and oral cancer KB) were evaluated. Compoun