53603-94-4

Usage

Uses

Used in Pharmaceutical Industry:
(22E)-6β-Methoxy-3β,5α-cyclostigmast-22-ene is used as an intermediate in the preparation of β-Sitosterol (S497050), a common plant sterol. β-Sitosterol has various health benefits, including cholesterol-lowering properties and anti-inflammatory effects. It is widely used in the formulation of dietary supplements and pharmaceutical products for the treatment of various conditions.
Used in Chemical Synthesis:
Due to its unique structure, (22E)-6β-Methoxy-3β,5α-cyclostigmast-22-ene can be used as a starting material for the synthesis of other complex organic compounds. Its double bond and methoxy group can be further modified or functionalized to produce a variety of chemical derivatives with potential applications in different industries.

Upstream product

• 67-56-1 methanol 
• 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 
• 53139-42-7 stigmasteryl tosylate 
• 83-48-7 Stigmasterol 
• 96572-90-6 Methanesulfonic acid (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-enyl ester 
• 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 
• 83787-28-4 (22S,23Z)-6β-methoxy-26-nor-3α,5-cyclo-5α-cholest-23-en-22-ol 
• 70813-67-1 (22S)-6β-methoxy-3α,5-cyclo-27-nor-5α-cholest-23-yn-22-ol 
• 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 
• 70813-69-3 (22E,24S)-6β-methoxy-3α,5-cyclo-24-ethyl-5α-cholest-22-en-26-oic acid ethyl ester 
• 104494-87-3 (22S,23S)-22,23-epoxy-6β-methoxy-3α,5-cyclo-5α-stigmastane 
• 105644-46-0 (22R,24R)-6β-methoxy-3α,5-cyclo-5α-stigmastan-22-ol 
• 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 
• 172376-20-4 (+)-(22R,23E,R_S)-22-hydroxy-6β-methoxy-23-(p-tolylsulfinyl)-3α,5-cyclo-5α-cholest-23-ene 

Downstream Products

• 915-05-9 stigmast-5-en-3-yl acetate 
• 25819-77-6 (20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde 
• 83-48-7 Stigmasterol 
• 51231-23-3 3α,5-cyclo-22-hydroxy-5α-23,24-bisnorcholan-6β-ol 6-methyl ether 
• 266309-04-0 3α,5-cyclo-22-hydroxy-5α-23,24-bisnorcholan-6α-ol 
• 69081-93-2 (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)-heptan-2-one 
• 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 

Relevant academic research and scientific papers

Absolute configuration assignment of stigmasterol oxiranes

Diastereoisomeric stigmasterol oxiranes 4, 5, 8, and 9 are known phytosterol oxidation products (POPs) that have been evaluated for their cytotoxicity, although the results are of limited significance since, in most cases, they were evaluated as mixtures. Consequently, to establish biological activity hierarchy of these oxides, it is critical to evaluate individual pure POPs. Therefore, we now describe the obtention of individual molecules and their absolute configuration (AC) determination. The two acetylated C-5?C-6 oxiranes 6 and 7; the two acetylated C-22?C-23 oxides 10 and 11, obtained by means of Δ5 double bond protection-deprotection; and the four C-5?C-6, C-22?C-23 diepoxystigmasteryl acetates 19–22 were now individually gained and their AC determined by vibrational circular dichroism. Vibrational modes associated with the C-5?C-6 and the C-22?C-23 bonds were identified in dioxiranes 19–22 and used to assign the AC of monoepoxides 6, 7, 10, and 11. The AC of biological active non-acetylated molecules follows immediately. Due to the scarce spectroscopic information available for these POPs, the 1H and 13C NMR chemical shifts of 3–22 were assigned using 1D- and 2D-NMR experiments.

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.

Synthesis of a Cholesterol Side-Chain Triazole Analogue via 'Click' Chemistry

An efficient preparation of a cholesterol analogue possessing a triazole ring is achieved starting from commercially available stigmasterol. The procedure is based on a [3+2] cycloaddition of a cholesterol possessing a side-chain terminal azide with a ter

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.

Access to functionalized steroid side chains via modified Julia olefination

Various functionalized steroidal side chains were conveniently accessed by a modified Julia olefination strategy using a common sulfone donor and an appropriate α-branched aldehyde acceptor. For the coupling of these hindered classes of reaction partners (and in contrast to typically observed trends), the benzothiazolyl(BT)-sulfone anion gave superior outcomes compared to the phenyltetrazolyl(PT)-sulfone anion.

NEUROTOXIC STEROL GLYCOSIDES

The invention relates to compositions for use in animal models of neurodegenerative disease and methods therefor. More particularly, the invention relates to the use of neurotoxic sterol glycosides or neurotoxic glycolipids, or combinations thereof, in animal models of neurodegenerative disease. Neurotoxicity-modulating chromenols can also be used in these animal models in combination with the neurotoxic sterol glycosides or neurotoxic glycolipids, or combinations thereof.

Synthesis and characterization of stigmasterol oxidation products

The synthesis and structural characterization of a series of oxides of stigmasterol is described providing a valuable series of reference standards for these oxides, analogous to the cholesterol oxidation products (COPs) which have been shown to have detrimental biological effects. Biological evaluation of the oxides of phytosterols is significant in the context of increased dietary use of phytosterols in the drive to reduce cholesterol absorption.

Synthesis of 28-homobrassinosteroids modified in the 26-position

28-Homobrassinosteroids modified in the 26-position were synthesized from 22-hydroxy-23-ensteroids using Claisen rearrangement and subsequent cis-hydroxylation of the resulting Δ22-derivative.

Δ5-7-Ketosterols with modified side chain: The synthesis and the effects on viability and cholesterol biosynthesis in Hep G2 cells

(22E)-3β-Hydroxysitosta-5,22-dien-7-one, (22R,23R)-3β,22,23- trihydroxysitost-5-en-7-one, and (22R,23R)-3β-hydroxy-22,23- isopropylidenedioxysitost-5-en-7-one were synthesized. The cytotoxicity and effects on cholesterol biosynthesis of the resulting 7-ketosterols, 7-ketocholesterol, and (22S,23S)-3β-hydroxy-22,23-oxidositost-5-en-7-one were studied in hepatoblastoma Hep G2 cells. Pleiades Publishing, Inc., 2006.