beta-Sitosterol (CHEM016541)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:36:29 UTC
Update Date2016-10-28 10:01:53 UTC
Accession NumberCHEM016541
Identification
Common Namebeta-Sitosterol
ClassSmall Molecule
DescriptionA member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3.
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(-)-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
SitosterolKegg
HarzolKegg
(-)-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
24-Ethylcholest-5-en-3 beta-olHMDB
24-EthylcholesterolHMDB
3beta-SitosterolHMDB
3beta-Stigmast-5-en-3-olHMDB
ClionasterolHMDB
Sitosterol, (3beta)-isomerHMDB
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
Stigmast-5-en-3beta-olHMDB
Stigmast-5-en-3β-olHMDB
delta5-Stigmasten-3beta-olHMDB
Δ5-stigmasten-3β-olHMDB
Α-phytosterolHMDB
RhammolHMDB
Δ5-stigmasten-3beta-olHMDB
beta-SitosterolChEBI
Chemical FormulaC29H50O
Average Molecular Mass414.718 g/mol
Monoisotopic Mass414.386 g/mol
CAS Registry Number83-46-5
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
Traditional 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
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
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.8e-05 g/LALOGPS
logP7.27ALOGPS
logP7.84ChemAxon
logS-7.4ALOGPS
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-054k-3912000000-22f633cd1bdd2ecca960Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aor-9810000000-ab4d6cb3490b23c5cb70Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-5947700000-fe0573c7669e97c469f5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-2931000000-0d63e91b728deb1446a4Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9822000000-2be95863c114e7cd2597Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9601000000-edade780f6cfb8ddc7d1Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-054k-3912000000-22f633cd1bdd2ecca960Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052v-1109000000-2eef6dd56a6c52421610Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-4103900000-a09c1c265657e57bd096Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0002900000-f2b81675160568c483c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05nb-3930100000-897e65b10be8a412585cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a59-6900000000-b62b8d1bd807fc41256bSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0aor-9810000000-fcbfd841778e213b3d3eSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-03di-5947700000-4234b723ccdb0e25d290Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positivesplash10-0002-2931000000-b2156fbd63c29312b076Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0a4l-9822000000-2be95863c114e7cd2597Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0019500000-b9eddfa8d56747167adaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-5139100000-42d184a108f9e994dc01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9076000000-54ef98673160128cbacdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-158617c2e43f1a46b58aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0004900000-632250471791929b07e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2019000000-717c6229722cf73f3faaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-eda302082c5114b2ab3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0001900000-86165feb8e32cd8692adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0001900000-1fc08db7654e3c4918f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4117900000-f005f19377309e9fb82dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06du-9146100000-d28aeb2182048e0912faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9511000000-ff6bd6e1f8902e32555dSpectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9821000000-0f43ba6def9281d5c86dSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000852
FooDB IDFDB012362
Phenol Explorer IDNot Available
KNApSAcK IDC00023770
BiGG IDNot Available
BioCyc IDCPD-4143
METLIN ID169
PDB IDNot Available
Wikipedia LinkBeta-Sitosterol
Chemspider ID192962
ChEBI ID27693
PubChem Compound ID222284
Kegg Compound IDC01753
YMDB IDNot Available
ECMDB IDM2MDB005635
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20525330
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23199991
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23215694
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23250922
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23266618
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23516045
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23624268
8. Trofimov, A. N.; Chuprova, V. A. Process for production of b-sitosterol from tall oil products. Khimiya Rastitel'nogo Syr'ya (2002), (2), 129-132.
9. Clayton PT, Bowron A, Mills KA, Massoud A, Casteels M, Milla PJ: Phytosterolemia in children with parenteral nutrition-associated cholestatic liver disease. Gastroenterology. 1993 Dec;105(6):1806-13.
10. Nguyen LB, Salen G, Shefer S, Bullock J, Chen T, Tint GS, Chowdhary IR, Lerner S: Deficient ileal 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in sitosterolemia: sitosterol is not a feedback inhibitor of intestinal cholesterol biosynthesis. Metabolism. 1994 Jul;43(7):855-9.
11. Barthomeuf C, Grassi J, Demeule M, Fournier C, Boivin D, Beliveau R: Inhibition of P-glycoprotein transport function and reversion of MDR1 multidrug resistance by cnidiadin. Cancer Chemother Pharmacol. 2005 Aug;56(2):173-81. Epub 2005 Apr 12.
12. Fernandez ML, Vega-Lopez S: Efficacy and safety of sitosterol in the management of blood cholesterol levels. Cardiovasc Drug Rev. 2005 Spring;23(1):57-70.
13. Gylling H, Miettinen TA: The effect of plant stanol- and sterol-enriched foods on lipid metabolism, serum lipids and coronary heart disease. Ann Clin Biochem. 2005 Jul;42(Pt 4):254-63.
14. Ling WH, Jones PJ: Dietary phytosterols: a review of metabolism, benefits and side effects. Life Sci. 1995;57(3):195-206.
15. Stalenhoef AF, Hectors M, Demacker PN: Effect of plant sterol-enriched margarine on plasma lipids and sterols in subjects heterozygous for phytosterolaemia. J Intern Med. 2001 Feb;249(2):163-6.
16. Siirtola A, Ketomaki A, Miettinen TA, Gylling H, Lehtimaki T, Holmberg C, Salo MK, Antikainen M: Cholesterol absorption and synthesis in pediatric kidney, liver, and heart transplant recipients. Transplantation. 2006 Feb 15;81(3):327-34.
17. Nikkila K, Hockerstedt K, Miettinen TA: Liver transplantation modifies serum cholestanol, cholesterol precursor and plant sterol levels. Clin Chim Acta. 1992 Jun 30;208(3):205-18.
18. Kabouche A, Boutaghane N, Kabouche Z, Seguin E, Tillequin F, Benlabed K: Components and antibacterial activity of the roots of Salvia jaminiana. Fitoterapia. 2005 Jul;76(5):450-2.
19. Sviridov DD, Safonova IG, Nano JL, Pavlov MY, Rampal P, Repin VS, Smirnov VN: New model to study cholesterol uptake in the human intestine in vitro. J Lipid Res. 1993 Feb;34(2):331-9.
20. Miwa K, Inazu A, Kobayashi J, Higashikata T, Nohara A, Kawashiri M, Katsuda S, Takata M, Koizumi J, Mabuchi H: ATP-binding cassette transporter G8 M429V polymorphism as a novel genetic marker of higher cholesterol absorption in hypercholesterolaemic Japanese subjects. Clin Sci (Lond). 2005 Aug;109(2):183-8.
21. Rajaratnam RA, Gylling H, Miettinen TA: Independent association of serum squalene and noncholesterol sterols with coronary artery disease in postmenopausal women. J Am Coll Cardiol. 2000 Apr;35(5):1185-91.
22. Madersbacher S, Schatzl G, Brossner C, Dreikorn K: [Phytotherapy for BPS. Which products can still be prescribed?]. Urologe A. 2005 May;44(5):513-20.
23. Honda A, Salen G, Honda M, Batta AK, Tint GS, Xu G, Chen TS, Tanaka N, Shefer S: 3-Hydroxy-3-methylglutaryl-coenzyme A reductase activity is inhibited by cholesterol and up-regulated by sitosterol in sitosterolemic fibroblasts. J Lab Clin Med. 2000 Feb;135(2):174-9.
24. Bhattacharyya AK, Lopez LA: Absorbability of plant sterols and their distribution in rabbit tissues. Biochim Biophys Acta. 1979 Jul 27;574(1):146-53.
25. Awad AB, Downie A, Fink CS, Kim U: Dietary phytosterol inhibits the growth and metastasis of MDA-MB-231 human breast cancer cells grown in SCID mice. Anticancer Res. 2000 Mar-Apr;20(2A):821-4.
26. Miettinen TA, Railo M, Lepantalo M, Gylling H: Plant sterols in serum and in atherosclerotic plaques of patients undergoing carotid endarterectomy. J Am Coll Cardiol. 2005 Jun 7;45(11):1794-801.
27. Kim BH, Lee YS, Kang KS: The mechanism of retinol-induced irritation and its application to anti-irritant development. Toxicol Lett. 2003 Dec 15;146(1):65-73.
28. Calpe-Berdiel L, Escola-Gil JC, Ribas V, Navarro-Sastre A, Garces-Garces J, Blanco-Vaca F: Changes in intestinal and liver global gene expression in response to a phytosterol-enriched diet. Atherosclerosis. 2005 Jul;181(1):75-85. Epub 2005 Feb 12.
29. Maguire L, Konoplyannikov M, Ford A, Maguire AR, O'Brien NM: Comparison of the cytotoxic effects of beta-sitosterol oxides and a cholesterol oxide, 7beta-hydroxycholesterol, in cultured mammalian cells. Br J Nutr. 2003 Oct;90(4):767-75.
30. Li JH, Awad AB, Fink CS, Wu YW, Trevisan M, Muti P: Measurement variability of plasma beta-sitosterol and campesterol, two new biomarkers for cancer prevention. Eur J Cancer Prev. 2001 Jun;10(3):245-9.
31. Wilt TJ, MacDonald R, Ishani A: beta-sitosterol for the treatment of benign prostatic hyperplasia: a systematic review. BJU Int. 1999 Jun;83(9):976-83.
32. Muti P, Awad AB, Schunemann H, Fink CS, Hovey K, Freudenheim JL, Wu YW, Bellati C, Pala V, Berrino F: A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women. J Nutr. 2003 Dec;133(12):4252-5.
33. Awad AB, Roy R, Fink CS: Beta-sitosterol, a plant sterol, induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells. Oncol Rep. 2003 Mar-Apr;10(2):497-500.