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S2424

Sigma-Aldrich

Stigmasterol

~95%

Synonyme(s) :

3β-hydroxy-24-éthyl-5,22-cholestadiène, 5,22-stigmastadiène-3β-ol

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About This Item

Formule empirique (notation de Hill) :
C29H48O
Numéro CAS:
83-48-7
Poids moléculaire :
412.69
Beilstein:
2568182
Numéro CE :
201-482-7
Numéro MDL:
MFCD00003630
Code UNSPSC :
12352211
ID de substance PubChem :
24899523
Nomenclature NACRES :
NA.77
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Essai

~95%

Niveau de qualité

100

Pf

165-167 °C (lit.)

Solubilité

chloroform: 50 mg/ml

Chaîne SMILES 

[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

Clé InChI

HCXVJBMSMIARIN-PHZDYDNGSA-N

Informations sur le gène

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

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Catégories apparentées

Application

Stigmasterol was used as a reference standard in determination of phytosterols in dietary supplements by gas chromatography[1] and in frozen leaf samples of Arabidopsis thaliana by GC/MS.[2]

Actions biochimiques/physiologiques

Stigmasterol is a phytosterol with chemical structure similar to cholesterol. It exhibits anti-cancer, anti-pyretic, anti-inflammatory and immune-modulating effects.[3][4] Stigmasterol decreases the expression of matrix metalloproteinases and reduced the degradation of cartilage in osteoarthritic rabbits.[3]

Notes préparatoires

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
0000431170
0000431170
0000345190
0000345190
0000231517

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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
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
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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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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