83-48-7

Basic information

• Product Name: Stigmasterol
• Synonyms: (24S)-24-Ethylcholesta-5,22-dien-3β-ol;(22E,24S)-24-Ethylcholesta-5,22-dien-3β-ol;(22E,24S)-Stigmasta-5,22-diene-3β-ol;Anti-stiffness factor;Stigmasterol,95%;Stigmasterol,3β-Hydroxy-24-ethyl-5,22-cholestadiene, 5,22-Stigmastadien-3β-ol, Stigmasterin;(3β,22E)-StigMasta-5,22-dien-3-ol;22-Dehydro-24-ethylcholesterol
• CAS NO: 83-48-7
• Molecular Formula: C29H48O
• Molecular Weight: 412.69
• EINECS: 201-482-7
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Steroids;Biochemistry;Hydroxysteroids
• Mol File: 83-48-7.mol
• Article Data: 19

Chemical Properties

• Melting Point: 165-167 °C(lit.)
• Boiling Point: 472.07°C (rough estimate)
• Flash Point: 219.4 °C
• Appearance: White/Powder
• Density: 0.9639 (rough estimate)
• Vapor Pressure: 9.21E-10mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: 0-6°C
• Solubility: chloroform: soluble50 mg/ml
• PKA: 15.03±0.70(Predicted)
• Water Solubility: insoluble
• Merck: 14,8815
• BRN: 2568182
• CAS DataBase Reference: Stigmasterol(CAS DataBase Reference)
• NIST Chemistry Reference: Stigmasterol(83-48-7)
• EPA Substance Registry System: Stigmasterol(83-48-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-38-40-48/20/22-36/37/38-67-36/38-20-63
• Safety Statements: 22-24/25-36/37-36-26
• RIDADR: UN 1888 6.1/PG 3
• WGK Germany: 3
• RTECS: WJ2447500
• Hazardous Substances Data: 83-48-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Stigmasterol is used as a precursor in the synthesis of progesterone, a valuable human hormone. It also plays a role in the biosynthesis of androgen, estrogen, and corticoids. Furthermore, it is utilized in the manufacture of vitamin D3 and cortisone.
Used in Food Industry:
Stigmasterol is found in foods such as margarines and yogurts, contributing to their nutritional profile.
Used in Research and Analysis:
Stigmasterol serves as an internal standard for the quantification of yeast cell wall sterols using gas chromatography-mass spectrometry (GC-MS) analysis. It is also used in the preparation of lipid monolayers for research purposes.
Used in Dietary Supplements:
As a dietary supplement, Stigmasterol can help reduce cholesterol levels in the human body, thus improving overall health.
Used in Cancer Research:
Stigmasterol has been used as a phytosterol compound to test its anti-proliferative property in breast cancer cell culture and its effect on liver X receptor-α (LXRA) activation.
Used in Health and Nutrition:
Dietary consumption of phytosterols, including stigmasterol, may have beneficial health effects in adults, particularly against cancer and ulceration. However, it is important to note that phytosterols may contribute to inflammation and intestinal failure-associated liver disease in young individuals.

References

https://en.wikipedia.org/wiki/Stigmasterol https://pubchem.ncbi.nlm.nih.gov/compound/Stigmasterin#section=Top

Biochem/physiol Actions

Stigmasterol possesses anti-inflammatory anti-hypercholestrolemic, antitumor and antioxidant functionality. It plays a crucial role in the activation of plasma membrane H+-ATPase and cell proliferation. Variations in stigmasterol and its precursor are noticeable at both the seed and whole plant developmental stages. Stigmasterol may be involved in gravitropism and tolerance to abiotic stress.

Purification Methods

Stigmasterol is best purified via the tetrabromide-acetate. The impure sterol (3g) is acetylated with Ac2O (60mL) by refluxing for 1.5hour. The mixture is cooled at 20o for 1hour, and the crude acetate is collected. The acetate (3g) in Et2O (30mL) is then treated with Br2/AcOH (38mL, from 5g Br2 in 100mL AcOH), and after cooling at 6o overnight, the tetrabromoacetate is filtered off and washed with Et2O. After six recrystallisations from CHCl3/MeOH the tetrabromoacetate has m 194-196o. This product (1g) in AcOH (12mL) and Zn dust (1g) is refluxed for 1.5hours, filtered hot, diluted with H2O (30mL) and extracted with Et2O. The extract is washed with dilute aqueous sodium sulfite, then H2O, the extract is dried (Na2SO4) and the stigmasterol acetate (~550mg) is recrystallised (4x) from EtOH and twice from MeOH/CHCl3 (2:1) to give the acetate with m 139-148o. This acetate (400mg) is hydrolysed in boiling 10% alcoholic KOH (1mL) for 1hour. Then H2O (30mL) is added and the mixture is extracted with Et2O. The extract is washed with aqueous Na2CO3, then H2O, the solvent is distilled off and the residue is recrystallised (3x) from 95% EtOH to give ~110mg of pure stigmasterol. It is dried in a vacuum over P2O5 for 3hours at 90o. The purity is checked by NMR. The acetate crystallises from MeOH with m 145o, [] D 25 -56o (c 2, CHCl3). [Byerrum & Ball Biochemical Preparations 7 86 1959, Thornton et al. J Am Chem Soc 62 2006 1940, Colin et al. Anal Chem 51 1661 1979, Beilstein 6 IV 4170.]

InChI:InChI=1/C29H48O/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/h8-9,19-22,24-27H,7,10-18H2,1-6H3/b9-8+/t20-,21-,22-,24+,25-,26+,27+,28+,29-/m1/s1

Upstream product

• 28831-63-2 prosaponin 
• 139894-63-6 22,23-dihydrostigmasteryl methyl ether 
• 19716-26-8 daucosterol 
• 1371577-45-5 stigmasterol-3-O-β-D-arabinopyranosyl [1->4]-O-β-D-glucopyranoside 
• 1262616-36-3 stigmasta-5,22-dien-3β-ol-3β-D-glucuropyranosyl-(6'β->1'')-glucopyranoside 
• 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 
• 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 
• 4651-48-3 stigmasterol acetate 
• 53139-42-7 stigmasteryl tosylate 
• 68-12-2 N,N-dimethyl-formamide 
• 178680-20-1 (2-{1-[(3S,8S,9S,10R,13R,14S,17R)-17-((E)-(1R,4S)-4-Ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-ethoxy}-ethyl)-trimethyl-silane 

Downstream Products

• 25819-77-6 (20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde 
• 83-46-5 β-sitosterol 
• 83-45-4 Stigmastanol 
• 915-05-9 stigmast-5-en-3-yl acetate 
• 2364-21-8 3β-acetoxy-5α-stigmastane 
• 20242-97-1 C₄₁H₇₀O₂ 
• 1174182-11-6 stigmasta-6,22-dien-3-yl 4-{(E)-[4-(dimethylamino)phenyl]diazenyl}benzoate 
• 1174182-10-5 stigmasta-6,22-dien-3-yl 4-[(E)-phenyldiazenyl]benzoate 
• 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 
• 51231-23-3 3α,5-cyclo-22-hydroxy-5α-23,24-bisnorcholan-6β-ol 6-methyl ether 

Relevant articles and documents

NOVEL METHOD FOR SYNTHESIZING 25-OH CHOLESTEROL/CALCIFEDIOL FROM PHYTOSTEROL

The present invention discloses novel method for synthesizing vegan 25-OH cholesterol/Calcifediol from inexpensive crude phytosterol. According to the method, Phytosterols are reacted to form corresponding i-steroid through tosylation and methanolysis. i-steroid on reductive ozonolysis to C-22 alcohol and conversion via C-22 tosylate to C-22 iodide in good yield. Coupling of C-22 tosylate with Grignard reagent of 4-bromo-2-methyl-2-[(trimethylsilyl)oxy] butane followed by deprotection yielded 25-OH cholesterol. In a process variant, nickel mediated conjugate addition of C-22 iodide to an electron deficient alkene ethyl acrylate and treating corresponding ester with methyl magnesium bromide as means of installing the side chain of 25-OH cholesterol in high yield. Further bromination reaction of 25-OH cholesterol diacetate followed by dehydrobromination using TBAF yielded 25-OH 7-dehydrocholesterol. Further photo reaction of 25-OH 7-dehydrocholesterol in to previtamin D3 using high or medium pressure mercury lamp and subsequent thermal reaction of previtamin D3 to 25-OH vitamin D3(Calcifediol) in good yield.

Stigmasteryl arachidate constituent from the straw of oryza sativa

One compound stigmasteryl-3β-arachidate (1) was isolated and identified from the rice straw of Oryza sativa. The structure of the compound was elucidated by 1D and 2D NMR (COSY, HSQC and HMBC) spectroscopic techniques aided by ESI-MS and IR spectra. To be

Stigmasterol-3-O-β-D-arabinopyranosyl(1→4)-O-β-D- glucopyranoside from the roots of Limonia crenulata (Roxb.)

The methanol soluble part of the concentrated ethanolic extract of defatted roots of Limonia crenulata (Roxb) when worked up phytochemically yielded a saponin which on various chemical reactions and spectral analysis was identified as; Stigmasterol-3-O-β- D-arabinopyranosyl (1→4)-O-β-D- glucopyranoside.

New steroidal glycosides from the stem bark of Mimusops elengi

Two new steroidal glycosides (1 and 2) have been isolated from the ethanolic extract of the stem bark of Mimusops elengi L. and characterized as stigmasta-5,22-dien-3β-ol-3β-D-glucuropyranosyl-(6'β→1'') -Dglucopyranoside (1) and β-sitosterol-3β-(3''',6'''

PROCESS FOR RECOVERING STEROLS FROM A CRUDE SOURCE CONTAINING STEROL ESTERS

A process of obtaining sterols suitable for human consumption from a crude wood pulping source containing sterol esters is disclosed. The sterols are obtained at high yield and purity. In particular, a process of obtaining sterols at high yield and purity from tall oil pitch (TOP) is disclosed. The sterols obtained can be esterified to sterol esters for use in dietary supplements and as additives for food and beverage products.

Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide

Dibutyltin oxide (DBTO) was first utilized for the deacetylation of steroid and diterpene esters. The results showed the deprotection of acetylated steroids and diterpenes separately with moderate catalysis dibutyltin oxide in methanol selectively removed part acetyl groups of these substrates, whereas several functional groups of the steroids and diterpenes were retained and neither isomerization nor degradation of these substrates was observed. It seems that the acetyl groups with lower steric hindrance or near carbonyl, alkoxy, or hydroxyl groups can be cleaved by the reaction, whereas the acetyl groups with higher steric hindrance or without carbonyl, alkoxy, or hydroxyl groups neighboring were retained under the same conditions. One of the interesting results obtained was the selective hydrolysis of the 3β-O-acetyl group in the presence of the 6β group in 3β,6β-Di-O-acetyl-5α-hydroxypregn-16-en-20-one. This allows for subsequent introduction of one unit at C-3 and the other unit at C-6. This procedure is useful for the synthesis of a series of closely related isomers of 3β,5α,6β-trihydroxypregn-16-en-20-one and other widespread polyhydroxysteroids in marine organisms and some terrestrial species.

Pentadecanoic acid β-D-glucoside from Clerodendrum inerme

A new aliphatic glucoside, isolated from the hexane extract of aerial parts of Clerodendrum inerme, has been characterized as pentadecanoic acid-β-D-glucoside, on the basis of spectral data analyses and chemical studies. Stigmasterol glucoside was also isolated from the same extract for the first time from this plant species. The butanol extract afforded acacetin and apigenin.

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.

Preparation of bile acids

Certain bile acids find use in the pharmaceutical industry. In view of the wide distribution of serious diseases such as HIV, AIDS and Bovine Spongiform Encephalopathy (BSE) it is desirable to avoid—as far as practicable—to have any components of animal origin in medicaments in order to eliminate any danger of infection. The present invention relates to a method of providing bile acids from non-animal starting materials.

Method of producing a vitamin product

A process for producing a nutrient supplement powder is provided. The process forms a powder into a plastic mass which is not completely molten. The plastic mass is then formed into an elongated shape and allowed to cool to set to a solid state. The solid is then comminuted to obtain a powder having a desirable particle size, e.g. not more than 5% by weight through a 120-mesh sieve and not more than 5% by weight retained on a 14-mesh sieve.