53603-94-4

Basic information

• Product Name: (22E)-6β-Methoxy-3β,5α-cyclostigmast-22-ene
• Synonyms: (22E)-6β-Methoxy-3β,5α-cyclostigmast-22-ene;(3β,5α,6β,22E)-3,5-CyclostigMast-22-ene 6-Methyl Ether
• CAS NO: 53603-94-4
• Molecular Formula: C₃₀H₅₀O
• Molecular Weight: 426.72
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 53603-94-4.mol
• Article Data: 21

Chemical Properties

• Melting Point: 55-56 °C
• Boiling Point: 484.5±14.0 °C(Predicted)
• Appearance: /
• Density: 0.98±0.1 g/cm3(Predicted)
• Solubility: Ethyl Acetate, Methyl Chloride
• CAS DataBase Reference: (22E)-6β-Methoxy-3β,5α-cyclostigmast-22-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (22E)-6β-Methoxy-3β,5α-cyclostigmast-22-ene(53603-94-4)
• EPA Substance Registry System: (22E)-6β-Methoxy-3β,5α-cyclostigmast-22-ene(53603-94-4)

Safety Data

• Hazardous Substances Data: 53603-94-4(Hazardous Substances Data)

Usage

Uses

(3β,5α,6β,22E)-3,5-Cyclostigmast-22-ene 6-Methyl Ether is an intermediate in the preparation of β-Sitosterol (S497050), a common plant sterol.

Upstream product

• 70813-82-0 (E)-(3S,6R)-3-Isopropyl-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-hept-4-en-1-ol 
• 83-48-7 Stigmasterol 
• 172376-34-0 (-)-(R_S)-(p-tolylsulfinyl)stigmasteryl isomethyl ether 
• 25819-77-6 (20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde 
• 105644-46-0 (22R,24R)-6β-methoxy-3α,5-cyclo-5α-stigmastan-22-ol 
• 104494-87-3 (22S,23S)-22,23-epoxy-6β-methoxy-3α,5-cyclo-5α-stigmastane 
• 53139-42-7 stigmasteryl tosylate 
• 67-56-1 methanol 
• 70813-71-7 (E)-(3S,6R)-3-Isopropyl-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-hept-4-enoic acid methyl ester 
• 70813-69-3 (22E,24S)-6β-methoxy-3α,5-cyclo-24-ethyl-5α-cholest-22-en-26-oic acid ethyl ester 
• 96572-89-3 (E)-(3R,6R)-3-Ethyl-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-methyl-hept-4-en-1-ol 
• 70813-67-1 (22S)-6β-methoxy-3α,5-cyclo-27-nor-5α-cholest-23-yn-22-ol 
• 83787-28-4 (22S,23Z)-6β-methoxy-26-nor-3α,5-cyclo-5α-cholest-23-en-22-ol 
• 172376-29-3 Methanesulfonic acid (E)-(R)-1-[(S)-1-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-4-methyl-2-((S)-toluene-4-sulfinyl)-pent-2-enyl ester 

Downstream Products

• 83-48-7 Stigmasterol 
• 56116-35-9 (S)-2-ethyl-3-dimethylbutan-1-ol 
• 51231-23-3 3α,5-cyclo-22-hydroxy-5α-23,24-bisnorcholan-6β-ol 6-methyl ether 
• 915-05-9 stigmast-5-en-3-yl acetate 
• 1065-41-4 O-(3.5-dinitro-benzoyl)-(β)-sitosterol 
• 1263469-78-8 5-(((S)-2-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethylhexadecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)propyl)thio)-1-phenyl-1H-tetrazole 
• 1263469-80-2 5-(((S)-2-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethylhexadecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)propyl)sulfonyl)-1-phenyl-1H-tetrazole 
• 1263469-87-9 (3α,5R,6β,22E,24S)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene 
• 1263469-89-1 (3α,5R,6β,22Z,24R)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene 
• 1263469-88-0 (3α,5R,6β,22E,24R)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene 
• 83-46-5 β-sitosterol 
• 75886-12-3 mutasterol 
• 266309-07-3 3α,5-cyclo-22(S)-phenylsulfonyl-23(R)-hydroxymethyl-5α-26,27-bisnorergost-6β,24-diol 6-methyl ester 
• 266309-09-5 3α,5-cyclo-22(R)-phenylsulfonyl-23(R)-hydroxymethyl-5α-26,27-bisnorergost-6β,24-diol 6-methyl ester 

Relevant articles and documents

On the mechanism of the dyotropic expansion of hydrindanes into decalins

A combined computational/experimental approach has revealed key mechanistic aspects in a recently reported dyotropic expansion of hydrindanes into decalins. While computer simulations had already anticipated the need for acid catalysis for making this reaction feasible under the mild conditions used in the laboratory, this work places the dyotropic step not into the reaction flask but at a later step, during the work up instead. With this information in hand the reaction has been optimized by exploring the performance of different activating agents and shown to be versatile, particularly in steroid related chemistry due to the two scaffolds that this reaction connects. Finally, the scope of the reaction has been significantly broadened by showing that this protocol can also operate in the absence of the fused six-member ring.

Formal Semisynthesis of Demethylgorgosterol Utilizing a Stereoselective Intermolecular Cyclopropanation Reaction

In this study, we report a convenient and high yielding formal semisynthesis of demethylgorgosterol, a marine steroid with an intriguing sidechain containing a cyclopropane unit. This was achieved through the synthesis of an advanced ketone intermediate.

Identification and characterization of β-sitosterol target proteins

β-Sitosterol is the most abundant plant sterol in the human diet. It is also the major component of several traditional medicines, including saw palmetto and devil's claw. Although β-sitosterol is effective against enlarged prostate in human clinical trials and has anti-cancer and anti-inflammatory activities, the mechanisms of action are poorly understood. Here, we report the identification of two new binding proteins for β-sitosterol that may underlie its beneficial effects.