Stigmasterol

Stigmasterol Basic information
Description References
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:83-48-7
MF:C29H48O
MW:412.7
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
Stigmasterol Structure
Stigmasterol Chemical Properties
Melting point 165-167 °C (lit.)
alpha -50 º (c=2, CHCl3)
Boiling point 472.07°C (rough estimate)
density 0.9639 (rough estimate)
refractive index 1.5000 (estimate)
storage temp. -20°C
solubility chloroform: soluble50 mg/ml
pka15.03±0.70(Predicted)
form Powder
color White
Water Solubility insoluble
λmax226nm(MeOH)(lit.)
Merck 14,8815
BRN 2568182
LogP10.072 (est)
CAS DataBase Reference83-48-7(CAS DataBase Reference)
NIST Chemistry ReferenceStigmasterol(83-48-7)
EPA Substance Registry SystemStigmasterol (83-48-7)
Safety Information
Hazard Codes Xn,Xi
Risk 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
HS Code 29309070
Hazardous Substances Data83-48-7(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Stigmasta-5,22-dien-3beta-ol English
SigmaAldrich English
ACROS English
Stigmasterol Usage And Synthesis
DescriptionStigmasterol is a kind of plant sterol or phytosterol. It is a kind of steroid derivative containing the hydroxyl group, unsaturated bonds, and alkyl group. It mainly exists in the fats and oils of soybean, Calabar bean, and rape seed as well as some kinds of vegetables, legumes and nuts. It can be used for the manufacture of semisynthetic progesterone which is a valuable human hormone. It can also be used in the biosynthesis of androgen, estrogen, and corticoids. Moreover, it can be used for the manufacture of vitamin D3 and cortisone. As a dietary supplement, it can reduce the cholesterol contained in the human body, thus boosting the health state of our body. 
Referenceshttps://en.wikipedia.org/wiki/Stigmasterol
https://pubchem.ncbi.nlm.nih.gov/compound/Stigmasterin#section=Top
DescriptionStigmasterol is a natural plant sterol that can be isolated from certain seed oils and herbs, including those used for therapeutic purposes. Dietary consumption of phytosterols, including stigmasterol, may have beneficial health effects in adults, particularly against cancer and ulceration. Alternatively, phytosterols may contribute to inflammation and intestinal failure-associated liver disease in young individuals.
Chemical Propertieswhite powder
UsesPlant sterol, used as a precursor in the synthesis of progesterone.
UsesStigmasterol 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. It may be used as an internal standard for the quantification of yeast cell wall sterols using gas chromatography–mass spectrometry (GC-MS) analysis, and in the preparation of lipid monolayers.
DefinitionChEBI: A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions.
General DescriptionStigmasterol is a plant sterol that comprises an unsaturated bond between C22 and C23. It is found in foods like margarines and yogurts. Stigmasterol is synthesized from the mevalonate pathway and is present during development stages in plants.
Biochem/physiol ActionsStigmasterol 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.
storage+4°C
Purification MethodsStigmasterol 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.]
Stigmasterol Preparation Products And Raw materials
Preparation ProductsDehydroepiandrosterone-->Stigmasta-4,22-diene-3,6-dione, (22E)-
STIGMASTEROL--N/H Stigmasterol,?98+%,STIGMASTEROL(P),STIGMASTEROL(RG) Phytosterol 90%,95% By Gc [Stigmasterol:83-48-7,-Sitosterol:83-46-5,Campesterol: 5,6-DIHYDROXY-BETA-STIGMASTEROL 7-ALPHA-HYDROXY-BETA-STIGMASTEROL STIGMASTEROL 1X1ML CHLOROFORM10MG/ML Phytosterol90%,95%ByGc(Stigmasterol:83-48-7,b-Sitosterol:83-46-5,Campesterol:476-62-4) 7-Dehydrosigmasterol Stigmasterol Stigmasterol, 22,23-dihydro- stigmasterol-24,28-epoxide 7-KETO-BETA-STIGMASTEROL STIGMASTEROL ACETATE Cholesterol 7-BETA-HYDROXY-BETA-STIGMASTEROL 25-DIHYDROXY-BETA-STIGMASTEROL (6E,22E)-(3R)-9,10-secoergosta-5(10),6,8,22-tetraen-3-ol 5,6-ALPHA/BETA-EPOXY-BETA-STIGMASTEROL

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