Record Information
Version1.0
Creation date2010-04-08 22:10:00 UTC
Update date2019-11-26 03:06:14 UTC
Primary IDFDB012131
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namegamma-Sitosterol
Descriptiongamma-Sitosterol, also known as plant steroid or phytosteroids, 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. gamma-Sitosterol is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number83-47-6
Structure
Thumb
Synonyms
SynonymSource
g-SitosterolGenerator
Γ-sitosterolGenerator
Plant steroidMeSH
PhytosteroidsMeSH
Plant sterolsMeSH
PhytosterolMeSH
Sterols, plantMeSH
Steroid, plantMeSH
PhytosterolsMeSH
Plant sterolMeSH
PhytosteroidMeSH
Steroids, plantMeSH
Sterol, plantMeSH
Plant steroidsMeSH
(24alphaFH)-stigmast-5-en-3beta-olbiospider
(3beta,8xi,9xi,10xi,13xi,14xi,17xi,24S)-stigmast-5-en-3-olbiospider
β-dihydrofucosterolbiospider
22,23-Dihydroporiferasterolbiospider
24β-Ethyl-5-cholesten-3β-olbiospider
24β-Ethylcholesterolbiospider
24b-Ethylcholest-5-en-3b-olbiospider
24b-Ethylcholesterolbiospider
24S-Ethylcholest-5-en-3β-olbiospider
24S-Ethylcholest-5-en-3b-olbiospider
Azuprostatbiospider
b-Dihydroeucosteroldb_source
B-dihydrofucosterolbiospider
Beta-dihydrofucosterolbiospider
Clionasteroldb_source
Fucosterol, β-dihydro-biospider
Gamma-sitosterolbiospider
Poriferast-5-en-3b-oldb_source
Stigmast-5-en-3-olbiospider
Stigmast-5-en-3-ol, (3β,24S)-biospider
Stigmast-5-en-3β-ol, (24S)-biospider
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
Polarizability53.73 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC29H50O
IUPAC name14-(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
InChI KeyKZJWDPNRJALLNS-UHFFFAOYSA-N
Isomeric SMILESCCC(CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C
Average Molecular Weight414.7067
Monoisotopic Molecular Weight414.386166222
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
  • Triterpenoid
  • Stigmastane-skeleton
  • C24-propyl-sterol-skeleton
  • 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 Descriptors
Ontology
OntologyNo ontology term
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 147-148°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -47.7 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052v-2109000000-4634b0fdc43ca6884d64JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-1019500000-cebb4a250ff7b3cd0451JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-5239100000-3964f60014b85da9ae29JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9083000000-e397f754f7f18147c3e2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-df9983661bb123d5991fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0005900000-732f16b49cc4559f4e92JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-3019000000-38804e054165030b517eJSpectraViewer
ChemSpider ID402901
ChEMBL IDNot Available
KEGG Compound IDC19654
Pubchem Compound ID457801
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00649
CRC / DFC (Dictionary of Food Compounds) IDCBR05-M:HDM54-S
EAFUS IDNot Available
Dr. Duke IDGAMMA-SITOSTEROL
BIGG IDNot Available
KNApSAcK IDC00023769
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
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).