83-47-6

Basic information

• Product Name: (3beta,24S)-stigmast-5-en-3-ol
• Synonyms: (3beta,24S)-stigmast-5-en-3-ol;(3b,24S)-stigmast-5-en-3-ol;Clionasterol;gamma-sitosterol;(24S)-Stigmast-5-en-3β-ol;22,23-Dihydroporiferasterol;beta-Dihydrofucosterol;Einecs 201-481-1
• CAS NO: 83-47-6
• Molecular Formula: C29H50O
• Molecular Weight: 414.7067
• EINECS: 201-481-1
• Mol File: 83-47-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 147 °C
• Boiling Point: 473.52°C (rough estimate)
• Flash Point: 220.4°C
• Appearance: /
• Density: 0.9540 (rough estimate)
• Vapor Pressure: 3.53E-12mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• PKA: 15.03±0.70(Predicted)
• CAS DataBase Reference: (3beta,24S)-stigmast-5-en-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3beta,24S)-stigmast-5-en-3-ol(83-47-6)
• EPA Substance Registry System: (3beta,24S)-stigmast-5-en-3-ol(83-47-6)

Safety Data

• Hazardous Substances Data: 83-47-6(Hazardous Substances Data)

Usage

General Description

(3beta,24S)-stigmast-5-en-3-ol, also known as β-sitosterol, is a plant sterol that is structurally similar to cholesterol. It is found in a variety of plant sources including nuts, seeds, and vegetables. β-sitosterol has been shown to have potential health benefits, including lowering cholesterol levels and reducing inflammation. It is also being studied for its potential anti-cancer and antidiabetic properties. Additionally, it has been used as a supplement to improve symptoms of benign prostatic hyperplasia (BPH) and to support the immune system. The chemical structure of (3beta,24S)-stigmast-5-en-3-ol plays a key role in its biological activities and potential health benefits.

InChI:InChI=1/C29H50O/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/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21+,23+,24+,25-,26+,27+,28+,29-/m1/s1

Upstream product

• 4651-54-1 3β-acetoxysitosterol 
• 96615-20-2 (1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-6-((1R,4S)-4-Ethyl-1,5-dimethyl-hexyl)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene 
• 106351-00-2 (3S,8S,9S,10R,13R,14S,17R)-17-((1R,4S)-4-Ethyl-1,5-dimethyl-hexyl)-3-methoxymethoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene 
• 83787-27-3 (22R,23Z)-6β-methoxy-26-nor-3α,5-cyclo-5α-cholest-23-en-22-ol 
• 83787-24-0 (22R)-6β-methoxy-3α,5-cyclo-27-nor-5α-cholest-23-yn-22-ol 
• 96615-18-8 ethyl (24S)-6β-methoxy-3α,5-cyclo-5α-stigmastan-26-oate 
• 70832-43-8 ethyl (22E,24S)-6β-methoxy-3α,5-cyclo-5α-stigmast-22-en-26-oate 
• 54604-87-4 6β-methoxy-3α,5-cyclo-24-nor-5α-chol-22-ene 
• 54604-91-0 2-[(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]-oxirane 
• 106350-89-4 (22S)-22-hydroxy-6β-methoxy-27-nor-3α,5-cyclo-5α-cholestan-24-one 
• 106350-86-1 (2S,3S)-1-(2-Ethyl-[1,3]dithian-2-yl)-3-((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)-butan-2-ol 
• 106350-93-0 (22S)-6β-methoxy-27-nor-3α,5-cyclo-5α-stigmast-24-en-26,22-lactone 
• 106350-94-1 (4S,6S)-4-Ethyl-6-[(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]-tetrahydro-pyran-2-one 
• 106401-63-2 (4S,6S)-4-Ethyl-6-[(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]-3-methyl-tetrahydro-pyran-2-one 

Downstream Products

• 18777-86-1 clionasterol benzoate 
• 67978-97-6 3β-phenylcarbamoyloxy-24α_FH-stigmastene-(5) 
• 1065-41-4 O-(3.5-dinitro-benzoyl)-clionasterol 
• 87100-47-8 4-(4-Undecyl-benzoyl)-benzoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((1R,4S)-4-ethyl-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 80860-62-4 C₅₇H₇₈O₇ 
• 897-06-3 Androsta-1,4-diene-3,17-dione 
• 71154-85-3 23,24-Bisnorchola-1,4-dien-3-on-22-oic acid 
• 23671-20-7 stigmast-4-en-3,6-dione 
• 2034-72-2 poriferasta-3,5-dien-7-one 
• 80860-62-4 C₅₇H₇₈O₇ 
• 105819-23-6 24α_FH-stigmast-4-en-3-one-(2,4-dinitro-phenylhydrazone) 

Relevant articles and documents

Process for recovery of plant sterols from by-product of vegetable oil refining

The process for recovery of plant sterols and tocopherols from deodorization distillates formed during chemical or physical refining of vegetable oils consists of the following steps: free fatty acids are removed from the deodorization distillate by vacuum distillation or by continuation solvent saponification, after the removal of free fatty acids, the received material is reacted with an aromatic carboxylic acid anhydride at a temperature of 50-150° C., under reduced pressure, after the treatment with anhydride, tocopherols are removed from the mixture, and crystalline free sterols are recovered from the distillation residue containing sterol esters, di- and triglycerides by transesterification.

Side Chain Structural Requirement for Utilization of Sterols by the Silkworm for Growth and Development. Non-stereoselective Utilization of the 24-Stereoisomeric Pairs of 24-Alkylsterols

Four C-24 epimeric pairs of 24-alkylsterols 1-8 were stereoselectively synthesized via orthoester Claisen rearrangement of the (22)R or (22S)-Δ23Z steroid derivatives (11 and 12).These compounds were tested on the silkworm larvae, Bombyx mori, in order to examine the relationship of the C-24 stereochemical arrangement and utilizability as a nutrient sterol.All of the tested sterols effectively supported the growth and development of the insect and were converted into cholesterol regardless of the C-24 configuration.Keywords - 24-alkylcholesterol; 24-alkyl-22-dehydrocholesterol; orthoester Claisen rearrangement; stereoselective synthesis; insect sterol; silkworm

Steroids from sponges

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