514-33-0

Basic information

• Product Name: (20S)-3β,16β-Dihydroxy-5α-pregnane-20-carboxylic acid γ-lactone
• Synonyms: (20S)-3β,16β-Dihydroxy-5α-pregnane-20-carboxylic acid γ-lactone;Tigogenin lactone
• CAS NO: 514-33-0
• Molecular Formula: C₂₂H₃₄O₃
• Molecular Weight: 346.5
• Mol File: 514-33-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 490.2°Cat760mmHg
• Flash Point: 195.4°C
• Appearance: /
• Density: 1.107g/cm³
• Vapor Pressure: 1.15E-11mmHg at 25°C
• Refractive Index: 1.532
• CAS DataBase Reference: (20S)-3β,16β-Dihydroxy-5α-pregnane-20-carboxylic acid γ-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: (20S)-3β,16β-Dihydroxy-5α-pregnane-20-carboxylic acid γ-lactone(514-33-0)
• EPA Substance Registry System: (20S)-3β,16β-Dihydroxy-5α-pregnane-20-carboxylic acid γ-lactone(514-33-0)

Safety Data

• Hazardous Substances Data: 514-33-0(Hazardous Substances Data)

Usage

General Description

"(20S)-3β,16β-Dihydroxy-5α-pregnane-20-carboxylic acid γ-lactone" is a chemical compound that belongs to the class of pregnane steroids. It is a derivative of progesterone and is formed by the addition of a carboxylic acid and a lactone group to the steroid backbone. (20S)-3β,16β-Dihydroxy-5α-pregnane-20-carboxylic acid γ-lactone has potential biological activity and may have pharmacological effects, especially in relation to hormone regulation and reproductive function. Further research is needed to fully understand the properties and potential uses of this compound in medicine and other fields.

InChI:InChI=1/C22H34O3/c1-12-19-18(25-20(12)24)11-17-15-5-4-13-10-14(23)6-8-21(13,2)16(15)7-9-22(17,19)3/h12-19,23H,4-11H2,1-3H3/t12-,13-,14-,15+,16-,17-,18-,19-,21-,22-/m0/s1

Upstream product

• 216572-46-2 (3β,5α,17Z)-3-{[(tert-butyl)dimethylsilyl]oxy}-21-pregn-17(20)-ene 
• 216572-47-3 (3β,5α,16α,17E)-3-{[(tert-butyl)dimethylsilyl]oxy}-pregn-17(20)-en-16-ol 
• 216572-48-4 (3β,5α,17E)-3-{[(tert-butyl)dimethylsilyl]oxy}-pregn-17(20)-en-16-one 
• 216572-49-5 (S)-2-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-16-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-propionitrile 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 6870-74-2 Dihydrosarsasapogenin 
• 126-18-1 smilagenin 
• 359416-36-7 3β-acetoxy-16β-hydroxy-5β-bisnorcholanoic acid 22->16 lactone 
• 77-60-1 tigogenin 
• 481-29-8 Epiandrosterone 
• 57711-44-1 (3S,10S,13S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta-[a]phenanthren-17-one 
• 216572-50-8 (S)-2-[(3S,5S,8R,9S,10S,13S,14S,16S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-16-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-propionitrile 
• 1061367-10-9 (S)-2-((3S,5S,8R,9S,10S,13S,14S,16S,17R)-3,16-Dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-propionitrile 

Downstream Products

• 1584133-07-2 C₃₈H₅₂O₃Si 
• 1584133-11-8 C₃₈H₅₄O₃Si 

Relevant articles and documents

Synthesis of "glycospirostanes" via ring-closing metathesis

Syntheses of "glycospirostanes" from 3β-hydroxy-23,24-dinor-5α-cholano-22,16-lactone and 3α-hydroxy-23,24-dinor-5β-cholano-22,16-lactone were performed. The key step of these syntheses was ring-closing metathesis of the corresponding C,O-diallyl derivativ

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Mechanistic studies of the rearrangements of steroidal 16,17-ketols and syntheses of 20→16-cis-γ-carbolactones

Utilization of 17-keto-androstanes as starting materials for the synthesis of α- or β-oriented steroidal 20→16-γ-carbolactones has been explored following two different strategies. A highly efficient, stereospecific protocol has been developed for the β-oriented cis-γ-lactone. A different approach, involving prior attachment of a 3-carbon side chain on C-17 of a 17-oxo-16β-acetoxy-androstane led to the epimeric, α-oriented lactone. The mechanism of the rearrangement of epimeric 16β- or 16α-hydroxy-17-keto-androstanes to 17β-hydroxy-16-keto-androstanes was studied by 13C NMR spectroscopy. The former occurs through a 1,2-sigmatropic H-shift, while the latter is likely to take place by simple enolization-reprotonation. Copyright (C) 1999 Elsevier Science Ltd.

Highly efficient and scalable synthesis of clionamine D

Herein we describe an efficient and scalable synthesis of clionamine D (4), a special member with autophagy bioactivity and an unprecedented spirobislactone side chain in the novel aminosteroid clionamines. This synthesis features a quick access to α-methylene-γ-lactone 8 and a Mn(OAc)3-mediated radical [3 + 2] reaction to assemble the unique spirobislactone unit. Clionamine D (4) can also serve as a key synthetic precursor to other clionamine members.