Record Information
Version1.0
Creation date2010-04-08 22:10:13 UTC
Update date2019-11-26 03:06:57 UTC
Primary IDFDB012521
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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
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
Predicted Properties
PropertyValueSource
Water Solubility2.2e-05 g/LALOGPS
logP6.81ALOGPS
logP7.4ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity125.17 m³·mol⁻¹ChemAxon
Polarizability52.06 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 83.93%; H 12.07%; O 3.99%DFC
Melting PointMp 157-158°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D -33 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-1019500000-05a81f76ea60f47816b3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lj-7149100000-434088453bcde1b45575JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-8093000000-5277512d6dbbe5d1ce17JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-cd4af4f76d04e1cacf46JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-4bea7e37de9105dc8905JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-3019000000-9b243f6f924e30b0b732JSpectraViewer
ChemSpider ID4446730
ChEMBL IDCHEMBL485421
KEGG Compound IDC01789
Pubchem Compound ID5283637
Pubchem Substance IDNot Available
ChEBI ID28623
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02869
CRC / DFC (Dictionary of Food Compounds) IDHHR44-Q:HHR45-R
EAFUS IDNot Available
Dr. Duke IDCAMPESTEROL
BIGG IDNot Available
KNApSAcK IDC00003647
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCampesterol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
hypocholesterolemicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.