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B4936

Sigma-Aldrich

Brassicasterol

from semisynthetic

Synonyme(s) :

5,22-Cholestadien-24β-methyl-3β-ol

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About This Item

Formule empirique (notation de Hill):
C28H46O
Numéro CAS:
474-67-9
Poids moléculaire :
398.66
Numéro CE :
207-486-5
Numéro MDL:
MFCD00201659
Code UNSPSC :
12352211
ID de substance PubChem :
329773247
Nomenclature NACRES :
NA.77

Source biologique

semisynthetic

Niveau de qualité

200

Essai

≥98% (TLC)

Forme

powder

Conditions d'expédition

wet ice

Température de stockage

2-8°C

Chaîne SMILES 

CC(C)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI

1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1

Clé InChI

OILXMJHPFNGGTO-ZAUYPBDWSA-N

Catégories apparentées

Application

Brassicasterol was used as standard to analyze the sterols from mussels sample by thin layer chromatography.

Actions biochimiques/physiologiques

Brassicasterol is a phytosterol found in rapeseed and canola oils; it is also present in marine algae and shellfish. Brassicasterol has been shown to inhibit sterol Δ24-reductase, an enzyme involved in the mammalian cholesterol biosynthesis pathway.
Brassicasterol is a plant sterol, structurally similar to cholesterol. Plant sterols compete with cholesterol and reduce the content of cholesterol incorporated into micelles thereby reducing its absorption. Brassicasterol reportedly decreases the progression of atherosclerosis. The level of brassicasterol in cerebrospinal fluid may be used as a prognostic factor for progression of Alzheimer′s disease.

Notes préparatoires

Brassicasterol is from a semi-synthetic source. It 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

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Certificats d'analyse (COA)

Lot/Batch Number
SLCM2946
SLCL2896
SLCJ3886
SLCJ1585
SLCH2014

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The search of new biomarkers to identify Alzheimer's disease: an editorial comment to T. Vanmierlo et al. 'The plant sterol brassicasterol and additional CFS biomarker in Alzheimer's Disease' (1).
A Lobo et al.
Acta psychiatrica Scandinavica, 124(3), 163-164 (2011-05-14)
T Vanmierlo et al.
Acta psychiatrica Scandinavica, 124(3), 184-192 (2011-05-19)
Plant sterols (sitosterol, campesterol, stigmasterol and brassicasterol) are solely dietary-derivable sterols that are structurally very similar to cholesterol. In contrast to peripheral cholesterol, plant sterols can cross the blood-brain barrier and accumulate within mammalian brain. As an impaired function of
Gavin Tansley et al.
Current gerontology and geriatrics research, 2012, 179318-179318 (2012-06-01)
Over the past 15 years, insights into sterol metabolism have improved our understanding of the relationship between lipids and common conditions such as atherosclerosis and Alzheimer's Disease (AD). A better understanding of sterol lipid metabolism in individuals with Down Syndrome
Maristela Pereira et al.
Biochimica et biophysica acta, 1801(10), 1163-1174 (2010-07-14)
The first committed step in the formation of 24-alkylsterols in the ascomycetous fungus Paracoccidiodes brasiliensis (Pb) has been shown to involve C24-methylation of lanosterol to eburicol (24(28)-methylene-24,25-dihydro-lanosterol) on the basis of metabolite co-occurrence. A similarity-based cloning strategy was employed to
E Heggen et al.
Nutrition, metabolism, and cardiovascular diseases : NMCD, 20(4), 258-265 (2009-09-15)
Data comparing the impact of different sources of plant sterols on CVD risk factors and antioxidant levels is scarce. We evaluated the effects of plant sterols from rapeseed and tall oils on serum lipids, lipoproteins, fat-soluble vitamins and plant sterol
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Cholesterol Biosynthesis Regulation

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