| Identification | Back Directory | [Name]
CAMPESTEROL | [CAS]
474-62-4 | [Synonyms]
C01789
CAMPESTROL
CAMPESTEROL
Campesterin
Campasterol
Mieyajunsu A
-17-((2R,5R)
Δ5-Campesterol
Ergost-5-en-3-ol
ERGOST-5-EN-3B-OL
CaMpest-5-en-3-ol
Campesterol, >=98%
Campesterol solution
ERGOST-5-EN-3-BETA-OL
(24R)-Ergost-5-en-3β-ol
(8R,9S,10S,13R,14S,17R)
campesterol from soybean
24alpha-Methylcholesterol
(24R)-5-Ergosten-3beta-ol
-5,6-Dimethylheptan-2-yl)
Ergost-5-en-3-ol, (3,24R)-
24(R)-ERGOST-5-EN-3BETA-OL
(24R)-24-Methylcholesterol
24α-methyl-5-cholesten-3β-ol
Ergost-5-en-3beta-ol, (24R)-
5-CHOLESTEN-24A-METHYL-3B-OL
Ergost-5-en-3-ol, (3beta,24R)-
DELTA5-24-Isoergosten-3beta-ol
5-CHOLESTEN-24A-METHYL-3BETA-OL
(24R)-Methylcholest-5-en-3beta-ol
(24R)-24-Methylcholest-5-en-3β-ol
5-Cholesten-24(RS)-Methyl-3-ol-d7
24ALPHA-METHYL-5-CHOLESTEN-3BETA-OL
5-CHOLESTEN-24-ALPHA-METHYL 3-BETA-OL
Campesterol from Glycine max (soybean)
CaMpesterol, froM Brassica caMpestris L.
Campesterol, 98%, from Brassica campestris L.
24α-Methyl-5-cholesten-3β-ol, 24(R)-Ergost-5-en-3β-ol
Campesterol,24α-Methyl-5-cholesten-3β-ol, 24(R)-Ergost-5-en-3β-ol
-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
17-(5,6-dimethylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol | [EINECS(EC#)]
207-484-4 | [Molecular Formula]
C28H48O | [MDL Number]
MFCD00010475 | [MOL File]
474-62-4.mol | [Molecular Weight]
400.68 |
| Chemical Properties | Back Directory | [Melting point ]
156-160 °C | [alpha ]
D23 -33° (22.5 mg in 5 ml chloroform) | [Boiling point ]
463.29°C (rough estimate) | [density ]
0.98±0.1 g/cm3 (20 ºC 760 Torr) | [refractive index ]
1.5100 (estimate) | [storage temp. ]
−20°C
| [solubility ]
Chloroform (Sparingly), Methanol (Slightly, Sonicated) | [form ]
crystalline
| [pka]
15.03±0.70(Predicted) | [color ]
white
| [Merck ]
13,1736 | [BRN ]
3216975 | [InChIKey]
SGNBVLSWZMBQTH-ZRUUVFCLSA-N | [LogP]
9.972 (est) |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
A phytosterol, which may inhibit the intestinal absorption of cholesterol. | [Description]
24α-methyl Cholesterol is a phytosterol found in vegetables, fruits, nuts, and seeds that competitively inhibits the absorption of intestinal cholesterol and decreases the transcription of genes important for cholesterol metabolism.1 The cholesterol lowering effects of phytosterols, such as 24α-methyl cholesterol, have been reported to be beneficial for lowering the incidence of atherosclerotic plaques.2 24α-methyl Cholesterol can also act as an agonist at liver X receptors (LXR) and, through activation of LXR signaling, has been shown to suppress the proliferation of prostate and breast cancer cells.3 | [Definition]
ChEBI: Campesterol is a member of phytosterols, a 3beta-sterol, a 3beta-hydroxy-Delta(5)-steroid and a C28-steroid. It has a role as a mouse metabolite. It derives from a hydride of a campestane. | [General Description]
Campesterol is a plant sterol, which is an analog of cholesterol and a brassinosteroid (BR) precursor. The enzyme diminute/dwarf1 mediates the synthesis of campesterol from 24-methylenecholesterol. Campesterol possesses methyl group at C-24 position of the side chain in the cholesterol structure. | [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. | [Purification Methods]
Campesterol is recrystallised twice from hexane and once from Me2CO. The benzoyl derivative has m 158-160o [] D 23 -8.6o (CHCl3), and the acetyl derivative has m 137138o (EtOH) and [] D 23 -35.1o (c 2.9, CHCl3) [Fernholz & MacPhillamy J Am Chem Soc 6 3 1155 1941]. [Beilstein 6 III 2680.] |
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