Record Information
Version1.0
Creation date2010-04-08 22:10:08 UTC
Update date2018-05-29 00:57:40 UTC
Primary IDFDB012362
Secondary Accession Numbers
  • FDB031179
  • FDB006298
Chemical Information
FooDB Namebeta-Sitosterol
Descriptionbeta-Sitosterol is one of several phytosterols (plant sterols) with chemical structures similar to that of cholesterol. Sitosterols are white, waxy powders with a characteristic odor. They are hydrophobic and soluble in alcohols. beta-Sitosterol is found in many foods, some of which are ginseng, globe artichoke, sesbania flower, and common oregano.
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
HarzolKegg
SitosterolKegg
(-)-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
b-SitosterolGenerator
Β-sitosterolGenerator
Sitosterol, (3beta,24xi)-isomerHMDB
3beta-Stigmast-5-en-3-olHMDB
gamma-SitosterolHMDB
Sitosterol, (3beta)-isomerHMDB
3beta-SitosterolHMDB
24-Ethylcholest-5-en-3 beta-olHMDB
24-EthylcholesterolHMDB
ClionasterolHMDB
Sitosterol, 26-(14)C-labeledHMDB
22,23-Dihydro-stigmasterolHMDB
a-PhytosterolHMDB
alpha-PhytosterolHMDB
AngelicinHMDB
beta-PhytosterolHMDB
CincholHMDB
D5-Stigmasten-3b-olHMDB
Delta5-Stigmasten-3b-olHMDB
PhytosterolHMDB
ProstasalHMDB
QuebracholHMDB
RhamnolHMDB
Sito-landeHMDB
SobatumHMDB
Stigmast-5-en-3-olHMDB
Stigmast-5-en-3b-olHMDB
beta-SitosterolChEBI
(-)-β-sitosterolGenerator
(3β)-stigmast-5-en-3-olGenerator
α-Dihydrofucosterolbiospider
α-Ethylcholesterolbiospider
β-Sitosterinbiospider
22,23-dihydro-StigmasterolHMDB
24-alpha-Ethylcholesterolbiospider
24α-Ethylcholesterolbiospider
24α-ethylcholesterolGenerator
Angelicin (steroid)manual
Beta-Sitosterinbiospider
Beta-Sitosterolbiospider
delta5-Stigmasten-3-beta-olbiospider
delta5-Stigmasten-3b-olbiospider
Papaveristeroldb_source
Raphanisteroldb_source
Sitosterol, βbiospider
Slanutosteroldb_source
Stigmast-5-en-3-beta-olbiospider
Stigmast-5-en-3-ol, (3β)-biospider
Stigmast-5-en-3-ol, (3beta)-biospider
Stigmast-5-en-3β-olbiospider
Stigmast-5-en-3beta-olbiospider
Stigmasterol, 22,23-dihydro-biospider
Verosteroldb_source
α-dihydrofucosterolGenerator
β-sitosterinGenerator
β-sitosterolGenerator
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
Bioavailability1ChemAxon
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
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 83.99%; H 12.15%; O 3.86%DFC
Melting PointMp 136-137°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D -35 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-054k-3912000000-22f633cd1bdd2ecca960View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aor-9810000000-ab4d6cb3490b23c5cb70View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-5947700000-fe0573c7669e97c469f5View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-2931000000-0d63e91b728deb1446a4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9822000000-2be95863c114e7cd2597View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9601000000-edade780f6cfb8ddc7d1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-054k-3912000000-22f633cd1bdd2ecca960View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052v-1109000000-2eef6dd56a6c52421610View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-4103900000-a09c1c265657e57bd096View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0002900000-f2b81675160568c483c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05nb-3930100000-897e65b10be8a412585cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a59-6900000000-b62b8d1bd807fc41256bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0aor-9810000000-fcbfd841778e213b3d3eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-03di-5947700000-4234b723ccdb0e25d290View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positivesplash10-0002-2931000000-b2156fbd63c29312b076View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0a4l-9822000000-2be95863c114e7cd2597View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0019500000-b9eddfa8d56747167adaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-5139100000-42d184a108f9e994dc01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9076000000-54ef98673160128cbacdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-158617c2e43f1a46b58aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0004900000-632250471791929b07e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2019000000-717c6229722cf73f3faaView in MoNA
MSMass Spectrum (Electron Ionization)splash10-052f-9821000000-0f43ba6def9281d5c86dView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID192962
ChEMBL IDCHEMBL221542
KEGG Compound IDC01753
Pubchem Compound ID222284
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00852
CRC / DFC (Dictionary of Food Compounds) IDCBR05-M:HGN93-D
EAFUS IDNot Available
Dr. Duke IDSITOSTEROL|BETA-SITOSTEROL
BIGG IDNot Available
KNApSAcK IDC00023770
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDBeta-Sitosterol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
androgenicDUKE
angiogenic50927 An agent that induces or stimulates the physiologic angiogenesis process.DUKE
anorexic50780 An agent which regulates the physiologic mechanisms that control the appetite and food intake.DUKE
anti adenomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti androgenic35497 A compound which inhibits or antagonises the biosynthesis or actions of androgens.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti edemicDUKE
anti estrogenic35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti feedantDUKE
anti fertilityDUKE
anti gonadotrophicDUKE
anti hyperlipoproteinaemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti lymphomicDUKE
anti mutagenicDUKE
anti ophidicDUKE
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
anti progestationalDUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti prostat adenomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti prostatiticDUKE
anti pyretic35493 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
apoptoticDUKE
artemicideDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
candidicideDUKE
caspase-8 inducerDUKE
estrogenicDUKE
febrifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
gonadotrophicDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hypocholesterolemicDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
hypolipidemicDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
spermicideDUKE
ubiquiotDUKE
ulcerogenicDUKE
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.