83-45-4

Basic information

• Product Name: STIGMASTANOL
• Synonyms: 24ALPHA-ETHYL-5ALPHA-CHOLESTAN-3BETA-OL;24-ALPHA-ETHYLCHOLESTANOL;24-ETHYL-5A-CHOLESTAN-3BETA-OL;24-ETHYLCHOLESTANOL;5-ALPHA-CHOLESTAN-24-BETA-ETHYL-3-BETA-OL;5,6-DIHYDRO-BETA-SITOSTEROL;BETA-SITOSTEROL, DIHYDRO-;BETA-SISTOSTANOL
• CAS NO: 83-45-4
• Molecular Formula: C29H52O
• Molecular Weight: 416.72
• EINECS: 201-479-0
• Mol File: 83-45-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: 144°C
• Boiling Point: 474.98°C (rough estimate)
• Appearance: /
• Density: 0.9444 (rough estimate)
• Refractive Index: 1.5000 (estimate)
• PKA: 15.14±0.70(Predicted)
• CAS DataBase Reference: STIGMASTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: STIGMASTANOL(83-45-4)
• EPA Substance Registry System: STIGMASTANOL(83-45-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24-26-36
• Hazardous Substances Data: 83-45-4(Hazardous Substances Data)

Usage

Description

Stigmastanol, also known as β-sitosterol, is a plant sterol that occurs naturally in various plant sources, including soybeans, corn, and wheat germ oil. It has a chemical structure similar to cholesterol and exhibits various health benefits due to its ability to lower cholesterol levels and exert anti-inflammatory effects.

Uses

Used in Food Industry:
Stigmastanol is used as a cholesterol-lowering agent in food product formulations for the prevention and treatment of hypercholesterolemia, hypertension, and inflammation disorders in humans. Its presence in the diet helps to reduce the absorption of dietary and biliary cholesterol, thereby lowering blood cholesterol levels and reducing the risk of cardiovascular diseases.
In addition to its cholesterol-lowering properties, stigmastanol also exhibits anti-inflammatory effects, making it a valuable ingredient in food products for managing inflammation-related disorders. Its incorporation into the diet can contribute to overall health and well-being by promoting cardiovascular health and reducing inflammation.

Upstream product

• 83-46-5 β-sitosterol 
• 915-05-9 stigmast-5-en-3-yl acetate 
• 481-14-1 Fucosterol 
• 64-19-7 acetic acid 
• 141-78-6 ethyl acetate 
• 51414-75-6 3α-chloro-5α-stigmastane 
• 127-08-2 potassium acetate 
• 109-52-4 valeric acid 
• 83-48-7 stigmasterol 
• 57815-95-9 stigmastadien-(4.22t)-yl-(3β)-acetate 
• 63631-47-0 3β-acetoxy-5α-stigmastene-(14) 
• 481-17-4 Spinasterol 
• 83-48-7 Stigmasterol 
• 2456-00-0 24-ethyl-cholesta-5,25-dien-3β-ol acetate 

Downstream Products

• 138706-00-0 (10S)-3c-(4-nitro-benzoyloxy)-10-r.13c-dimethyl-17c-((1R:4R)-1.5-dimethyl-4-ethyl-hexyl)-(5tH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthrene 
• 4736-94-1 stigmastan-3-one 
• 107493-31-2 (24R)-5α-stigmastan-3β-ol benzoate 
• 106774-76-9 3-O-(trans-4-feruloyl)-β-sitostanol 
• 677324-56-0 C₃₇H₅₆O₄ 
• 677324-57-1 C₃₈H₅₈O₄ 
• 1164-95-0 androsterone acetate 
• 53-41-8 cis-androsterone 
• 106774-74-7 3-O-(trans-4-O-acetylferuloyl)-β-sitostanol 
• 152602-30-7 5α-Sigmastan-3α-yl m-Iodobenzoate 
• 6160-48-1 3.5-dinitro-benzoic acid-(5α-stigmastanyl-(3β)-ester) 
• 18089-48-0 3β-(toluene-sulfonyl-(4)-oxy)-5α-stigmastane 

Relevant articles and documents

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7-DEHYDROSITOSTEROL FROM RAUWOLFIA SERPENTINA

7-Dehydrositosterol has been isolated from the roots of Rauwolfia serpentina. Key Word Index - Rauwolfia serpentina; Apocynaceae; 7-dehydrositosterol.

Novel approach to determining the absolute configurations at the C3-positions of various types of sterols based on an induced circular dichroism

Circular dichroism (CD) spectra of the 2,2′-binaphthyl ester derived from Δ5-sterols showed not bisignate CD but diagnostic CD bands at around 210 and 240 nm. These bands might be attributable to an interaction between an olefinic chromophore and a binaphthyl one. Various types of unsaturated sterols were thus derivatized followed by complete hydrogenation, to give saturated sterols. As a result, CD spectra of the binaphthyl derivatives of the saturated sterols showed bisignate curves centered at 240 nm (3S(β): positive chirality; 3R(α): negative one). This suggested a straightforward and practical method for discriminating the absolute stereogenic center at the C-3 positions of sterols based on an induced CD. This finding should contribute significantly to the analysis of metabolites of various types of sterols.

Synthesis of highly pure oxyphytosterols and (oxy)phytosterol esters. Part I. Regioselective hydrogenation of stigmasterol: An easy access to oxyphytosterols

The synthesis of several oxyphytosterols is described starting from stigmasterol, the key step being the regioselective hydrogenation of the 22-23 double bond of the latter.