20817-72-5

Basic information

• Product Name: STIGMASTADIENONE
• Synonyms: (22E)-Stigmasta-4,22-dien-3-one;4,22-Stigmastadiene-3-one;crytalline;Stigmasta-4,22-dien-3-one;4,22-Cholestadien-24-ethyl-3-one;24-Ethyl-4,22E-cholestadien-3-one;(8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS NO: 20817-72-5
• Molecular Formula: C₂₉H₄₆O
• Molecular Weight: 410.67494
• Mol File: 20817-72-5.mol
• Article Data: 18

Chemical Properties

• Melting Point: 123-127 °C
• Boiling Point: 503.2°Cat760mmHg
• Flash Point: 262.3°C
• Appearance: /
• Density: 0.98g/cm³
• Vapor Pressure: 2.97E-10mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: STIGMASTADIENONE(CAS DataBase Reference)
• NIST Chemistry Reference: STIGMASTADIENONE(20817-72-5)
• EPA Substance Registry System: STIGMASTADIENONE(20817-72-5)

Safety Data

• Hazardous Substances Data: 20817-72-5(Hazardous Substances Data)

Usage

Uses

Stigmastadienone is used in biological studies for the isolation and characterization of antiinflammatory diterpenoids from Croton tonkinensis.

InChI:InChI=1/C29H46O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-9,18-21,24-27H,7,10-17H2,1-6H3/b9-8+/t20?,21-,24?,25?,26?,27?,28+,29-/m1/s1

Upstream product

• 83-48-7 stigmasterol 
• 64-19-7 acetic acid 
• 83-48-7 stigmasterol 
• 7647-01-0 hydrogenchloride 
• 65527-29-9 stigmastadiene-(5,22t)-diol-(3β,4β) 
• 83-48-7 Stigmasterol 
• 51529-12-5 stigmasta-5,22-dien-3β-ol 
• 86166-35-0 stigmasterol tetrabromide 

Downstream Products

• 76740-15-3 (S)-2-ethyl-3-methylbutanal 
• 57-83-0 Progesterone 
• 54412-02-1 Stigmast-22-en 
• 20817-73-6 stigmastadien-(4.22t)-one-(3)-semicarbazone 
• 26254-92-2 α-ethylisovaleraldehyde 
• 3986-89-8 (20S)-3-oxopregn-4-ene-20-carboxaldehyde 
• 76692-30-3 3-Oxobisnor-4-cholenaldehyde diethyl acetal 
• 4736-56-5 (24S)-5α-stigmast-22(E)-en-3β-ol 
• 53106-51-7 benzoic acid-(5β-stigmasten-(22t)-yl-(3α)-ester) 
• 108814-74-0 benzoic acid-(5α-stigmasten-(22t)-yl-(3β)-ester) 
• 5405-37-8 5β-stigmasten-(22t)-yl-(3α)-acetate 
• 5405-37-8 24-ethyl-5α-cholest-22-en-3β-yl acetate 
• 83-45-4 Stigmastanol 
• 110556-84-8 (2S,3S,4R,5S)-3-Ethyl-2-methyl-5-phenylselanyl-6-((1R,3aS,3bR,5aS,6aS,9aR,10aS,10bS,12aS)-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-1-yl)-heptan-4-ol 

Relevant articles and documents

Ruthenium-catalyzed Oppenauer-type oxidation of 3β-hydroxy steroids. A highly efficient entry into the steroidal hormones with 4-en-3-one functionality

Oxidation of 5-unsaturated 3β-hydroxy steroids 1 to the corresponding 4-en-3-one derivatives 2 can be performed efficiently by acetone at reflux in the presence of a catalytic system consisting of either (PPh3)3RuCl2 (3) and K2CO3 or [(C4Ph4COHOCC4Ph4)(μ-H)][(CO)4Ru2] (4). The reaction proceeds via a ruthenium-catalyzed dehydrogenation of 1 and subsequent hydrogen transfer to acetone with concomitant double bond migration.

Structure and synthesis of a progesterone homologue from the skin of the dorid nudibranch Aldisa smaragdina

The short-side-chain steroid 24-norchol-4-ene-3,22-done (6) has been found to be the main metabolite of both skin and mucus of the mollusc Aldisa smaragdina. This compound, previously reported as a microbial degradation product of cholesterol, has never previously been isolated from natural sources. The absolute stereochemistry was determined by synthesis from commercial stigmasterol, and a full NMR characterisation is also reported. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

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Synthesis and search for 3β,3′β-disteryl ethers after high-temperature treatment of sterol-rich samples

It has been proven that at increased temperature, sterols can undergo various chemical reactions e.g., oxidation, dehydrogenation, dehydration and polymerisation. The objectives of this study are to prove the existence of dimers and to quantitatively analyse the dimers (3β,3′β-disteryl ethers). Sterol-rich samples were heated at 180 °C, 200 °C and 220 °C for 1 to 5 h. Quantitative analyses of the 3β,3′β-disteryl ethers were conducted using liquid extraction, solid-phase extraction and gas chromatography coupled with mass spectrometry. Additionally, for the analyses, suitable standards were synthetized from native sterols. To identify the mechanism of 3β,3′β-disteryl ether formation at high temperatures, an attempt was made to use the proposed synthesis method. Additionally, due to the association of sterols and sterol derivatives with atherosclerosis, preliminary studies with synthetized 3β,3′β-disteryl ethers on endothelial cells were conducted.

Pincer and diamine Ru and Os diphosphane complexes as efficient catalysts for the dehydrogenation of alcohols to ketones

The ruthenium and osmium complexes [MCl2(diphosphane)(L)] (M=Ru, Os; L=bidentate amino ligand) and [MCl(CNN)(dppb)] (CNN=pincer ligand; dppb=1,4-bis- (diphenylphosphino)butane), containing the N-H moiety, have been found to catalyze the acceptorless dehydrogenation of alcohols in tBuOH and in the presence of KOtBu. The compounds trans-[MCl2(dppf)(en)] (M=Ru 7, Os 13; dppf=1,1′-bis(diphenylphosphino)ferrocene; en=ethylenediamine) display very high activity and different substrates, including cyclic and linear alcohols, are efficiently oxidized to ketones by using 0.8-0.04mol% of catalyst. The effect of the base and the comparison of the catalytic activity of the Ru versus Os complexes are reported. The ruthenium complex 7 generally leads to a faster conversion into ketones with respect to the osmium complex 13, which displays better activity in the dehydrogenation of 5-en-3β-hydroxy steroids. The synthesis of new Ru and Os complexes [MCl2(PP)(L)] (PP=dppb, dppf; L=(±)-trans-1,2-diaminocyclohexane, 2-(aminomethyl) pyridine, and 2-aminoethanol) of trans and cis configuration is also reported. Alcohol breakdown: Ruthenium and osmium phosphane complexes containing nitrogen ligands with the N-H functionality efficiently catalyze the acceptorless dehydrogenation of alcohols. With [MCl2(dppf)(en)] (M=Ru, Os; dppf=1,1′-bis(diphenylphosphino)ferrocene; en=ethylenediamine) in the presence of KOtBu several alcohols have been converted into ketones (see scheme), including sterols for which Os displays a better activity than Ru. Copyright