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Stigmasterol

CAS No.
83-48-7
Chemical Name:
Stigmasterol
Synonyms
PHYTOSTEROL;beta-Stigmasterol;STIGMASTERIN;I-Stigmasterol;Stigmasterol,95%;Stig;NSC 8095;masteroL;201-482-7;Serposterol
CBNumber:
CB4333449
Molecular Formula:
C29H48O
Molecular Weight:
412.7
MDL Number:
MFCD00003630
MOL File:
83-48-7.mol
MSDS File:
SDS
Last updated:2023-09-14 16:39:47

Stigmasterol Properties

Melting point 165-167 °C (lit.)
Boiling point 472.07°C (rough estimate)
alpha -50 º (c=2, CHCl3)
Density 0.9639 (rough estimate)
refractive index 1.5000 (estimate)
storage temp. -20°C
solubility chloroform: soluble50 mg/ml
form Powder
pka 15.03±0.70(Predicted)
color White
Water Solubility insoluble
λmax 226nm(MeOH)(lit.)
Merck 14,8815
BRN 2568182
LogP 10.072 (est)
CAS DataBase Reference 83-48-7(CAS DataBase Reference)
FDA UNII 99WUK5D0Y8
NIST Chemistry Reference Stigmasterol(83-48-7)
EPA Substance Registry System Stigmasterol (83-48-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08
Signal word  Danger
Hazard statements  H302-H315-H319-H331-H336-H351-H361d-H372-H412
Precautionary statements  P201-P273-P301+P312+P330-P302+P352-P304+P340+P311-P308+P313
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
NFPA 704
0
1 0

Stigmasterol price More Price(43)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich S2424 Stigmasterol ~95% 83-48-7 1g $64.5 2024-03-01 Buy
Sigma-Aldrich S2424 Stigmasterol ~95% 83-48-7 5g $253 2024-03-01 Buy
Sigma-Aldrich PHL82658 Stigmasterol phyproof? Reference Substance 83-48-7 100MG $262 2024-03-01 Buy
Sigma-Aldrich 47132 Stigmasterol certified reference material, 10?mg/mL in chloroform 83-48-7 1mL $56.9 2024-03-01 Buy
TCI Chemical S0088 Stigmasterol >90.0%(GC) 83-48-7 1g $51 2024-03-01 Buy
Product number Packaging Price Buy
S2424 1g $64.5 Buy
S2424 5g $253 Buy
PHL82658 100MG $262 Buy
47132 1mL $56.9 Buy
S0088 1g $51 Buy

Stigmasterol Chemical Properties,Uses,Production

Description

Stigmasterol 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. 

References

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

Description

Stigmasterol 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 Properties

white powder

Uses

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. 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.

Uses

Plant sterol, used as a precursor in the synthesis of progesterone.

Definition

ChEBI: A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions.

General Description

Stigmasterol 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 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.

storage

+4°C

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.]

83787-28-4
83-48-7
Synthesis of Stigmasterol from 3,5-Cyclo-27-norcholest-23-en-22-ol, 6-methoxy-, (3β,5α,6β,22R,23Z)- (9CI)

Stigmasterol Preparation Products And Raw materials

Global( 460)Suppliers
Supplier Tel Email Country ProdList Advantage
Shaanxi Pioneer Biotech Co., Ltd .
+8613259417953 sales@pioneerbiotech.com China 3000 58
Hebei Mojin Biotechnology Co., Ltd
+8613288715578 sales@hbmojin.com China 12456 58
Henan Bao Enluo International TradeCo.,LTD
+86-17331933971 +86-17331933971 deasea125996@gmail.com China 2503 58
airuikechemical co., ltd.
+undefined86-15315557071 sales02@airuikechemical.com China 994 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21691 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070 product@chemlin.com.cn CHINA 3012 60
Nanjing Finetech Chemical Co., Ltd.
025-85710122 17714198479 sales@fine-chemtech.com CHINA 885 55
Shanghai Zheyan Biotech Co., Ltd.
18017610038 zheyansh@163.com CHINA 3620 58
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29914 58
Shaanxi Yikanglong Biotechnology Co., Ltd.
17791478691 yklbiotech@163.com CHINA 296 58

View Lastest Price from Stigmasterol manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Stigmasterol pictures 2024-04-26 Stigmasterol
83-48-7
US $300.00 / kilograms 10kilograms 99% 10 Hebei Dangtong Import and export Co LTD
Stigmasterol pictures 2024-04-23 Stigmasterol
83-48-7
US $0.00-0.00 / kg 1kg ≥95% HPLC 1000kg Changsha Staherb Natural Ingredients Co., Ltd.
Stigmasterol pictures 2024-04-11 Stigmasterol
83-48-7
US $0.00-0.00 / Kg 1Kg 99.99% 2000 tons airuikechemical co., ltd.
  • Stigmasterol pictures
  • Stigmasterol
    83-48-7
  • US $300.00 / kilograms
  • 99%
  • Hebei Dangtong Import and export Co LTD
  • Stigmasterol pictures
  • Stigmasterol
    83-48-7
  • US $0.00-0.00 / kg
  • ≥95% HPLC
  • Changsha Staherb Natural Ingredients Co., Ltd.
  • Stigmasterol pictures
  • Stigmasterol
    83-48-7
  • US $0.00-0.00 / Kg
  • 99.99%
  • airuikechemical co., ltd.
(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,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 5,22-StigMastadiene-3β-ol StigMasterol, 95% 5GR 24-Ethyl-5,22-cholestadien-3β-ol 24β-Ethyl-5,22-cholestadien-3β-ol NSC 8095 StigMasterol (StigMasterin) Serposterol Stigmasta-5,22-dien-3b-ol Stigmasta-5,22-dien-3-ol, (3b,22E)- (24S)-24-Ethyl-22,23-didehydrocholesterol Stigmasterol Stigmasta-5,22-dien-3beta-ol 201-482-7 3BETA-HYDROXY-24-ETHYL-5,22-CHOLESTADIENE [3B-HYDROXY-24-ETHYL-D] ZZ-CHOLESTADIENE 5,22-STIGMASTADIEN-3-BETA-OL 5,22-CHOLESTADIEN-24B-ETHYL-3BETA-OL 5,22-CHOLESTADIEN-24BETA-ETHYL-3BETA-OL (24S)-5,22-STIGMASTADIEN-3BETA-OL 3β-Hydroxy-24-ethyl-5,22-cholestadiene 5,22-Stigmastadien-3β-ol Stigmasta-5,22-dien-3beta-ol STIGMASTEROL STIGMASTA-5,22-DIEN-3-OL, (3BETA)- STIGMASTA-5,22-DIEN-3BETA-OL (22E)-Stigmasta-5,22-dien-3-ol 5,22-Cholestadien-24-ethyl-3beta-ol DELTA5,22-Stigmastadien-3beta-ol Stigmasta-5,22-dien-3-ol Stigmasta-5,22-dien-3-ol, (3beta,22E)- 3β-Hydroxy-24-ethyl-5,22-cholestadiene 5,22-Stigmastadien-3β-ol 24-Ethylcholesta-5,22-dien-3beta-ol 17-(5-ethyl-6-methyl-hept-3-en-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol STIGMASTEROL extrapure 3β-Hydroxy-24-ethyl-5,22-cholestadiene, 5,22-Stigmastadien-3β-ol, Stigmasterin (24S)-24-Ethylcholesta-5,22-dien-3b-ol (3b,22E)-Stigmasta-5,22-dien-3-ol 2-(4-Chlorophenyl)sulfanylethanol Stigmasterol, >90.0%(GC) (5R,8R,9S,10S,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Stigmasterol > stigmasterol 94% masteroL Stig Stigmasta-5,22-dien-3-ol, (3β,22E)- Reduce Cholesterol Soybean Extract Phytosterol powder Stigmasterol USP/EP/BP (3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol Stigmasterol,95% STIGMASTERIN PHYTOSTEROL beta-Stigmasterol I-Stigmasterol