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S2424

Stigmasterol

~95%

Synonym(s):

3β-Hydroxy-24-ethyl-5,22-cholestadiene, 5,22-Stigmastadien-3β-ol, Stigmasterin

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About This Item

Empirical Formula (Hill Notation):
C29H48O
CAS Number:
83-48-7
Molecular Weight:
412.69
UNSPSC Code:
12352211
NACRES:
NA.77
PubChem Substance ID:
24899523
EC Number:
201-482-7
Beilstein/REAXYS Number:
2568182
MDL number:
MFCD00003630
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assay

~95%

Quality Level

100

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

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

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.

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Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000431170
0000431170
0000345190
0000231517
0000345190

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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
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