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S2424

Sigma-Aldrich

Stigmasterol

~95%

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Synonym(s):
3β-Hydroxy-24-ethyl-5,22-cholestadiene, 5,22-Stigmastadien-3β-ol, Stigmasterin
Empirical Formula (Hill Notation):
C29H48O
CAS Number:
Molecular Weight:
412.69
Beilstein/REAXYS Number:
2568182
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

assay

~95%

mp

165-167 °C (lit.)

solubility

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

InChI key

HCXVJBMSMIARIN-PHZDYDNGSA-N

Gene Information

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1 of 4

This Item
47132B4936PHL82658
vibrant-m

S2424

Stigmasterol

vibrant-m

47132

Stigmasterol

vibrant-m

B4936

Brassicasterol

vibrant-m

PHL82658

Stigmasterol

solubility

chloroform: 50 mg/ml

solubility

-

solubility

-

solubility

-

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

-

mp

165-167 °C (lit.)

mp

165-167 °C (lit.)

mp

-

mp

165-167 °C (lit.)

Gene Information

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

Gene Information

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

Gene Information

-

Gene Information

-

Application

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 Actions

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.

Preparation Note

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Beta-sitosterol European Pharmacopoeia (EP) Reference Standard

Y0001615

Beta-sitosterol

β-Sitosterol United States Pharmacopeia (USP) Reference Standard

USP

1612947

β-Sitosterol

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
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
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
Wei-Ping Chen et al.
Acta biochimica Polonica, 59(4), 537-541 (2012-10-18)
Stigmasterol has been shown exhibit anti-osteoarthritic properties in vitro studies. However, the in vivo effects of stigmasterol on cartilage are still unclear. This study investigated the anti-osteoarthritic properties of stigmasterol on cartilage degradation in a rabbit model of osteoarthritis (OA).

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