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S2424

Sigma-Aldrich

Stigmasterol

~95%

Synonym(e):

3β-Hydroxy-24-ethyl-5,22-cholestadien, 5,22-Stigmastadien-3β-ol, Stigmasterol

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About This Item

Empirische Formel (Hill-System):
C29H48O
CAS-Nummer:
83-48-7
Molekulargewicht:
412.69
Beilstein:
2568182
EG-Nummer:
201-482-7
MDL-Nummer:
MFCD00003630
UNSPSC-Code:
12352211
PubChem Substanz-ID:
24899523
NACRES:
NA.77

Assay

~95%

Qualitätsniveau

100

mp (Schmelzpunkt)

165-167 °C (lit.)

Löslichkeit

chloroform: 50 mg/ml

SMILES String

[H][C@@]12[C@]([C@](CC[C@H](O)C3)(C)C3=CC2)([H])CC[C@@]4(C)[C@@]1([H])CC[C@]4([H])[C@]([H])(C)/C=C/[C@@H](CC)C(C)C

InChI

1S/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/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

InChIKey

HCXVJBMSMIARIN-PHZDYDNGSA-N

Angaben zum Gen

human ... POLA1(5422) , TOP2A(7153)
rat ... Polb(29240)

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Anwendung

Stigmasterol was used as a reference standard in determination of phytosterols in dietary supplements by gas chromatography and in frozen leaf samples of Arabidopsis thaliana by GC/MS.

Biochem./physiol. Wirkung

Stigmasterol is a phytosterol with chemical structure similar to cholesterol. It exhibits anti-cancer, anti-pyretic, anti-inflammatory and immune-modulating effects. Stigmasterol decreases the expression of matrix metalloproteinases and reduced the degradation of cartilage in osteoarthritic rabbits.

Angaben zur Herstellung

Stigmasterol yields clear, colorless solution in chloroform at 50 mg/ml.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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β-Sitosterol primary reference standard

02090580

β-Sitosterol

Brassicasterol Avanti Research™ - A Croda Brand

Avanti

700175P

Brassicasterol

Fucosterol ≥93%

Sigma-Aldrich

F5379

Fucosterol

sitostanol β-sitostanol, powder

Avanti

700121P

sitostanol

β-Sitosterol European Pharmacopoeia (EP) Reference Standard

Y0001615

β-Sitosterol

β-Sitosterol United States Pharmacopeia (USP) Reference Standard

USP

1612947

β-Sitosterol

Thomas Griebel et al.
The Plant journal : for cell and molecular biology, 63(2), 254-268 (2010-05-07)
Upon inoculation with pathogenic microbes, plants induce an array of metabolic changes that potentially contribute to induced resistance or even enhance susceptibility. When analysing leaf lipid composition during the Arabidopsis thaliana-Pseudomonas syringae interaction, we found that accumulation of the phytosterol
Poonamjot Deol et al.
Endocrinology, 161(2) (2020-01-09)
Soybean oil consumption has increased greatly in the past half-century and is linked to obesity and diabetes. To test the hypothesis that soybean oil diet alters hypothalamic gene expression in conjunction with metabolic phenotype, we performed RNA sequencing analysis using
Timo Basen et al.
Oecologia, 170(1), 57-64 (2012-03-09)
The accumulation of cyanobacterial biomass may severely affect the performance of aquatic consumers. Here, we investigated the role of sterols in determining the food quality of cyanobacteria for the invasive clam Corbicula fluminea, which has become a common benthic invertebrate
A B Awad et al.
The Journal of nutrition, 130(9), 2127-2130 (2000-08-26)
Phytosterols (PS) or plant sterols are structurally similar to cholesterol. The most common PS are beta-sitosterol, campesterol and stigmasterol. Epidemiologic and experimental studies suggest that dietary PS may offer protection from the most common cancers in Western societies, such as
Michael J Twiner et al.
Genomics, 91(3), 289-300 (2008-01-15)
Azaspiracid-1 (AZA-1) is a marine biotoxin reported to accumulate in shellfish from several countries, including eastern Canada, Morocco, and much of western Europe, and is frequently associated with severe gastrointestinal human intoxication. As the mechanism of action of AZA-1 is
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