C5157

Campesterol

~65%

• Synonym(s): 24α-Methyl-5-cholesten-3β-ol, 24(R)-Ergost-5-en-3β-ol
• Empirical Formula (Hill Notation): C₂₈H₄₈O
• CAS Number: 474-62-4
• Molecular Weight: 400.68
• Beilstein/REAXYS Number: 3216975
• EC Number: 207-484-4
• MDL number: MFCD00010475
• UNSPSC Code: 12352211
• PubChem Substance ID: 24892762
• NACRES: NA.28

Properties

• biological source: Glycine max (soybean)
• form: powder
• concentration: ~65%
• shipped in: ambient
• storage temp.: −20°C
• 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
• 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
• InChI key: SGNBVLSWZMBQTH-ZRUUVFCLSA-N

Description

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.

Quality

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).

Preparation Note

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

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302 + H312 + H332,H315,H319,H335
• pcodes: P261 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P305 + P351 + P338
• 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
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves