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Campesterol (PC000900)

Record Information
Version1.0
Creation date2015-10-09 22:33:18 UTC
Update date2017-01-19 02:36:40 UTC
FoodComEx IDPC000900
FoodDB RecordFDB012521
Chemical Information
NameCampesterol
DescriptionConstituent of rapeseed oil (Brassica napa), soybean oil (Glycine max) and wheatgerm oil (Triticum subspecies). Found in virtually all plant oils Campesterol is a phytosterol, meaning it is a steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15%.; ; The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. -- Wikipedia; Presence of brassicasterol, together with auxiliary markers ?-linolenic acid and erucic acid, is a marker of adulteration of soybean oil and sunflower oil with rapeseed oil. As there is no brassicasterol in sunflower and soybean oil, but its concentration in rapeseed oil is about 1400 mg/kg, the amount of rapeseed oil added can be calculated.
CAS Number474-62-4
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(24R)-5-Ergosten-3-beta-olbiospider
(24R)-5-Ergosten-3α-Methylcholesterolbiospider
(24R)-5-Ergosten-3β-olbiospider
(24R)-5-Ergosten-3b-olbiospider
(24R)-Ergost-5-en-3-beta-olbiospider
(24R)-Ergost-5-en-3b-olbiospider
(24R)-Methylcholest-5-en-3β-olbiospider
(24R)-Methylcholest-5-en-3b-olbiospider
(3-beta-24R)-Ergost-5-en-3-olbiospider
(3-beta)-Ergost-5-en-3-olbiospider
(3b,24R)-Ergost-5-en-3-olbiospider
(3b)-Ergost-5-en-3-olGenerator
(3beta)-Ergost-5-en-3-olChEBI
(3β)-ergost-5-en-3-olGenerator
«DELTA»5-24-Isoergosten-3β-olbiospider
24-alpha-Methylcholesterolbiospider
24-methyl-5-Cholestene-3-olbiospider
24-Methylcholest-5-en-3beta-olbiospider
24α-Methyl-5-cholesten-3β-olbiospider
24α-Methylcholesterolbiospider
24a-Methyl-5-cholesten-3b-olbiospider
24a-Methylcholesterolbiospider
5-Cholestene-3-ol, 24-methyl-biospider
Campesterinbiospider
Campesteroldb_source
Campestrolbiospider
EB 82Adb_source
Ergost-5-en-3-beta-olbiospider
Ergost-5-en-3-olbiospider
Ergost-5-en-3-ol, (3β,24R)-biospider
Ergost-5-en-3β-ol, (24R)-biospider
Mieyajunsu Adb_source
Chemical FormulaC28H48O
IUPAC name(2R,5S,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
InChI IdentifierInChI=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-/m1/s1
InChI KeySGNBVLSWZMBQTH-MMTVXVTESA-N
Isomeric SMILESCC(C)[C@H](C)CC[C@@H](C)C1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
Average Molecular Weight400.6801
Monoisotopic Molecular Weight400.370516158
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointMp 157-158°DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 2 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Not Available