83-48-7 Usage
Description
Stigmasterol, a plant sterol or phytosterol, is a steroid derivative characterized by the presence of a hydroxyl group, unsaturated bonds, and an alkyl group. It is primarily found in the fats and oils of soybean, Calabar bean, and rape seed, as well as in various vegetables, legumes, and nuts. Stigmasterol is synthesized through the mevalonate pathway and is present during the development stages in plants. It is a white powder and is also known as a 3beta-sterol with double bonds at the 5,6and 22,23-positions.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 83-48-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 3 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 83-48:
(4*8)+(3*3)+(2*4)+(1*8)=57
57 % 10 = 7
So 83-48-7 is a valid CAS Registry Number.
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
83-48-7Relevant articles and documents
NOVEL METHOD FOR SYNTHESIZING 25-OH CHOLESTEROL/CALCIFEDIOL FROM PHYTOSTEROL
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Page/Page column 18-19, (2020/11/23)
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.
Stigmasterol-3-O-β-D-arabinopyranosyl(1→4)-O-β-D- glucopyranoside from the roots of Limonia crenulata (Roxb.)
Shrivastava, Archana,Parihar, Sangeeta,Jadhav, Raina
, p. 171 - 175 (2013/07/19)
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.
PROCESS FOR RECOVERING STEROLS FROM A CRUDE SOURCE CONTAINING STEROL ESTERS
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Page/Page column 3, (2008/12/06)
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.
