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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)

Lot/Batch Number
027K5302
047H5033
036K5319
056H5001
044K5320

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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
Poliana Guerino Marson Ascêncio et al.
Evidence-based complementary and alternative medicine : eCAM, 2014, 190543-190543 (2015-01-15)
Costus spiralis (Costaceae) is a species native to the Amazon region and is used in traditional medicine. The endophytic fungi used in this study were obtained from leaves of this plant. 13 strains were selected to obtain hydroethanolic extracts and
Wendy R Sorenson et al.
Journal of AOAC International, 89(1), 22-34 (2006-03-04)
In conjunction with an AOAC Presidential Task Force on Dietary Supplements, a method was validated for measurement of 3 plant sterols (phytosterols) in saw palmetto raw materials, extracts, and dietary supplements. AOAC Official Method 994.10, "Cholesterol in Foods," was modified
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