Record Information
Version1.0
Creation date2010-04-08 22:07:04 UTC
Update date2020-09-17 15:31:15 UTC
Primary IDFDB006298
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhytosterol
DescriptionBeta-sitosterol, also known as sitosterol or harzol, belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Beta-sitosterol is widely distributed in the plant kingdom and is a main dietary phytosterol (a plant sterol) found in vegetable oils, nuts, avocados and prepared foods, such as salad dressings. Phytopharmacological extracts, commonly derived from the South African star grass, Hypoxis rooperi, or from species of Pinus and Picea, contain mixtures of phytosterols, that includes Beta-sitosterol. However, these extracts also contain some sterols bonded with glucosides. While beta-sitosterol is the purported active constituent, beta-sitosterol-beta-D-glucoside is often detected. Thus, one or both metabolites may be the active components. Phytosterols, like cholesterol, contain double bonds that are susceptible to oxidation. Beta-sitosterol may have anti-carcinogenic and anti-atherogenic properties (PMID: 13129445, 11432711). Benign prostatic hyperplasia patients treated with beta-sitosterol, compared with placebo, had improved urinary symptom scores and flow measures (PMID: 10368239). Hyperandrogenic postmenopausal women, with higher risk of breast cancer because of their endocrine profiles, were placed on a plant food-based diet, to determine if eating a plant-based diet, rich in phytosterols, rather than animal-based diet, would have an increase in serum phytosterols. Compared to controls, women placed on the plant-based diet had increased serum phytosterols, particularly beta-sitosterol, suggesting that beta-sitosterol can be used as a biomarker of exposure in observational studies or as a compliance indicator in dietary intervention studies of cancer prevention (PMID: 14652381). Beta-sitosterol induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells (PMID: 12579296). Although the exact mechanism of action of beta-sitosterols in the above studies is unknown, it may be related to cholesterol metabolism or anti-inflammatory effects (via interference with prostaglandin metabolism).
CAS Number83-46-5
Structure
Thumb
Synonyms
SynonymSource
(-)-beta-SitosterolChEBI
(24R)-Ethylcholest-5-en-3beta-olChEBI
(24R)-Stigmast-5-en-3beta-olChEBI
(3beta)-Stigmast-5-en-3-olChEBI
22,23-DihydrostigmasterolChEBI
24alpha-EthylcholesterolChEBI
alpha-DihydrofucosterolChEBI
AzuprostatChEBI
beta-SitosterinChEBI
CupreolChEBI
NimbosterolChEBI
TriastonalChEBI
(-)-b-SitosterolGenerator
(-)-β-SitosterolGenerator
b-SitosterolGenerator
β-SitosterolGenerator
(24R)-Ethylcholest-5-en-3b-olGenerator
(24R)-Ethylcholest-5-en-3β-olGenerator
(24R)-Stigmast-5-en-3b-olGenerator
(24R)-Stigmast-5-en-3β-olGenerator
(3b)-Stigmast-5-en-3-olGenerator
(3β)-Stigmast-5-en-3-olGenerator
24a-EthylcholesterolGenerator
24α-EthylcholesterolGenerator
a-DihydrofucosterolGenerator
α-DihydrofucosterolGenerator
b-SitosterinGenerator
β-SitosterinGenerator
22,23-Dihydro-StigmasterolHMDB
a-PhytosterolHMDB
alpha-PhytosterolHMDB
AngelicinHMDB
beta-PhytosterolHMDB
CincholHMDB
D5-Stigmasten-3b-olHMDB
Delta5-Stigmasten-3b-olHMDB
HarzolHMDB, KEGG
PhytosterolHMDB
ProstasalHMDB
QuebracholHMDB
RhamnolHMDB
sito-LandeHMDB
SitosterolHMDB, KEGG
SobatumHMDB
Stigmast-5-en-3-olHMDB
Stigmast-5-en-3b-olHMDB
3beta-SitosterolMeSH, HMDB
24-Ethylcholest-5-en-3 beta-olMeSH, HMDB
24-EthylcholesterolMeSH, HMDB
ClionasterolMeSH, HMDB
3beta-Stigmast-5-en-3-olMeSH, HMDB
Sitosterol, (3beta)-isomerMeSH, HMDB
beta-SitosterolChEBI
Stigmast-5-en-3beta-olHMDB
Stigmast-5-en-3β-olHMDB
delta5-Stigmasten-3beta-olHMDB
Δ5-Stigmasten-3β-olHMDB
α-PhytosterolHMDB
RhammolPhytoBank
Δ5-Stigmasten-3beta-olPhytoBank
Phytosterolsmanual
Plant sterolsmanual
Predicted Properties
PropertyValueSource
Water Solubility1.8e-05 g/LALOGPS
logP7.27ALOGPS
logP7.84ChemAxon
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 Count6ChemAxon
Refractivity129.77 m³·mol⁻¹ChemAxon
Polarizability54.21 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC29H50O
IUPAC name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
InChI IdentifierInChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChI KeyKZJWDPNRJALLNS-VJSFXXLFSA-N
Isomeric SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C
Average Molecular Weight414.718
Monoisotopic Molecular Weight414.38616623
Classification
Description belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassStigmastanes and derivatives
Direct ParentStigmastanes and derivatives
Alternative Parents
Substituents
  • C24-propyl-sterol-skeleton
  • Stigmastane-skeleton
  • Triterpenoid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-054k-3912000000-22f633cd1bdd2ecca960JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aor-9810000000-ab4d6cb3490b23c5cb70JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-5947700000-fe0573c7669e97c469f5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-2931000000-0d63e91b728deb1446a4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9822000000-2be95863c114e7cd2597JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9601000000-edade780f6cfb8ddc7d1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-054k-3912000000-22f633cd1bdd2ecca960JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052v-1109000000-2eef6dd56a6c52421610JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-4103900000-a09c1c265657e57bd096JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0002900000-f2b81675160568c483c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05nb-3930100000-897e65b10be8a412585cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a59-6900000000-b62b8d1bd807fc41256bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0aor-9810000000-fcbfd841778e213b3d3eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-03di-5947700000-4234b723ccdb0e25d290JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positivesplash10-0002-2931000000-b2156fbd63c29312b076JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0a4l-9822000000-2be95863c114e7cd2597JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0019500000-b9eddfa8d56747167adaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-5139100000-42d184a108f9e994dc01JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9076000000-54ef98673160128cbacdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-158617c2e43f1a46b58aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0004900000-632250471791929b07e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2019000000-717c6229722cf73f3faaJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-052f-9821000000-0f43ba6def9281d5c86dJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID26125
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDPHYTOSTEROL|PHYTOSTEROLS
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPhytosterol
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
anti prostatoticDUKE
hypocholesterolemicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).