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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%

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)

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