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Merck

C5157

Campesterol

~65%

Synonyme(s) :

24α-Methyl-5-cholesten-3β-ol, 24(R)-Ergost-5-en-3β-ol

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A propos de cet article

Formule empirique (notation de Hill) :
C28H48O
Numéro CAS:
Poids moléculaire :
400.68
UNSPSC Code:
12352211
NACRES:
NA.28
PubChem Substance ID:
EC Number:
207-484-4
Beilstein/REAXYS Number:
3216975
MDL number:
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InChI key

SGNBVLSWZMBQTH-ZRUUVFCLSA-N

InChI

1S/C28H48O/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/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1

SMILES string

[H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[H])[C@H](C)CC[C@H](C)C(C)C

biological source

Glycine max (soybean)

form

powder

concentration

~65%

shipped in

ambient

storage temp.

−20°C

Quality Level

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Catégories apparentées

Application

Campesterol was used as standard in GC and HPLC analysis of oil samples from plants.

Biochem/physiol Actions

Campesterol is a phytosterol, primarily found in nuts, fruits, legumes and seeds. Though an analogue of cholesterol, it is poorly absorbed in humans and competitively inhibits the absorption of cholesterol. Campesterol decreases the transcription of genes involved in cholesterol metabolism in hepatocytes and enterocytes and has positive impact in treatment of cardiovascular disease.
Plant sterol. May lower absorption of dietary cholesterol.

Preparation Note

Campesterol yields clear, colorless to faint yellow solution in chloroform at 20 mg/ml.

Analysis Note

Appears ~98% by HPLC and GC, but has been shown by 13C-NMR to contain ~35% dihydrobrassicasterol (24β-methyl-5-cholesten-3β-ol; 24[S]-ergost-5-en-3β-ol).

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Consulter la Bibliothèque de documents

Kang Jiang et al.
Journal of the American Society for Mass Spectrometry, 30(9), 1700-1712 (2019-05-22)
Phytosterols and tocopherols are essential for plant biochemistry, and they possess beneficial health effects for humans. Evaluating the tandem mass spectrometric (MS/MS) behavior of phytosterols and tocopherols is needed for the development of a qualitative and quantitative method for these
Juan P Barrios-Ramos et al.
Journal of the science of food and agriculture, 92(11), 2349-2357 (2012-03-21)
The effect of functional foods alone or in combination (cocoa + soy + oats + fish oil) on hepatic damage in rats affected with metabolic syndrome was investigated. Rats that were given cocoa showed a decrease in the levels of
D Lütjohann et al.
Journal of lipid research, 36(8), 1763-1773 (1995-08-01)
Absorption of dietary cholesterol, campesterol, and sitosterol, cholesterol balance, and fecal excretion of plant sterols were determined in three unrelated patients with phytosterolemia and three healthy volunteers during constant intake of cholesterol and plant sterols using accurate gas-liquid chromatography-mass spectrometry
Hannu Päivä et al.
Clinical pharmacology and therapeutics, 78(1), 60-68 (2005-07-09)
Myopathy, probably caused by 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibition in skeletal muscle, rarely occurs in patients taking statins. This study was designed to assess the effect of high-dose statin treatment on cholesterol and ubiquinone metabolism and mitochondrial function in human skeletal
S H Kasmas et al.
Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas, 45(11), 1095-1101 (2012-07-18)
Effective statin therapy is associated with a marked reduction of cardiovascular events. However, the explanation for full benefits obtained for LDL cholesterol targets by combined lipid-lowering therapy is controversial. Our study compared the effects of two equally effective lipid-lowering strategies

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