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HomeProduct name listCAMPESTEROL

CAMPESTEROL

Synonym(s):24α-Methyl-5-cholesten-3β-ol;24(R)-Ergost-5-en-3β-ol;campest-5-en-3β-ol

  • CAS NO.:474-62-4
  • Empirical Formula: C28H48O
  • Molecular Weight: 400.69
  • MDL number: MFCD00010475
  • EINECS: 207-484-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
CAMPESTEROL Structural

What is CAMPESTEROL?

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. The cholesterol lowering effects of phytosterols, such as 24α-methyl cholesterol, have been reported to be beneficial for lowering the incidence of atherosclerotic plaques. 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.

Chemical properties

White Solid

The Uses of CAMPESTEROL

Campesterol may be used as a plant sterol to test its effect on the transcriptional activation of liver X receptor α (LXRA) in breast cancer cells. It may also be used as a sterol standard for calibration curve generation in liquid chromatography multiple reaction monitoring (LC-MRM) analysis.

The Uses of CAMPESTEROL

A phytosterol, which may inhibit the intestinal absorption of cholesterol.

What are the applications of Application

Campesterol is a plant sterol used for research purposes

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.]

Properties of CAMPESTEROL

Melting point: 156-160 °C
Boiling point: 463.29°C (rough estimate)
alpha  D23 -33° (22.5 mg in 5 ml chloroform)
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

Safety information for CAMPESTEROL

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for CAMPESTEROL

InChIKey SGNBVLSWZMBQTH-ZRUUVFCLSA-N

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