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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-08-17 21:43:34 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameBeta-Sitosterol
DescriptionBeta-Sitosterol, a main dietary phytosterol found in plants, may have the potential for prevention and therapy for human cancer. (PMID: 146129380 ). Phytosterols are plant sterols found in foods such as oils, nuts and vegetables. Phytosterols, in the same way as cholesterol, contain a double bond and are susceptible to oxidation, and are characterized by anti-carcinogenic and anti-atherogenic properties. (PMID: 13129445 , 11432711 ). beta-sitosterol is a phytopharmacological extract containing a mixture of phytosterols, with smaller amounts of other sterols, bonded with glucosides. These phytosterols are commonly derived from the South African star grass, Hypoxis rooperi, or from species of Pinus and Picea. The purported active constituent is termed beta-sitosterol. Additionally, the quantity of beta-sitosterol-beta-d-glucoside is often reported. Although the exact mechanism of action of beta-sitosterols is unknown it may be related to cholesterol metabolism or anti-inflammatory effects (via interference with prostaglandin metabolism). Compared with placebo, beta-sitosterol improved urinary symptom scores and flow measures. (PMID: 10368239 ). A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women. This finding indicate that beta-sitosterol can be used as biomarker of exposure in observational studies or as compliance indicators 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 ).
Chemical FormulaC29H50O
Average Molecular Weight414.7067
Monoisotopic Molecular Weight414.386166222
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
Traditional Namesitosterol
CAS Registry Number83-46-5
InChI Identifier
Chemical Taxonomy
DescriptionThis compound 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
  • Polycyclic triterpenoid
  • Triterpenoid
  • Stigmastane-skeleton
  • C24-propyl-sterol-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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
StatusDetected and Quantified
  • Drug
  • Food
  • Plant
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
Experimental Properties
Melting Point140 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility1.84e-05 mg/mLALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity129.77 m3·mol-1ChemAxon
Polarizability54.21 Å3ChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-054k-3912000000-22f633cd1bdd2ecca960View 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
MSMass Spectrum (Electron Ionization)splash10-052f-9821000000-0f43ba6def9281d5c86dView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Prostate
  • Testes
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified22.8 +/- 6.7 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified5.53 +/- 0.021 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.902 +/- 0.089 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Not AvailableNormal details
UrineDetected and Quantified0.00017 +/- 0.000095 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BloodDetected and Quantified14.1 +/- 10.6 uMAdult (>18 years old)BothShort bowel syndrome details
UrineDetected and Quantified0.0021 umol/mmol creatinineAdult (>18 years old)FemaleSitosterolemia details
Associated Disorders and Diseases
Disease References
Short bowel syndrome
  1. Ellegard L, Sunesson A, Bosaeus I: High serum phytosterol levels in short bowel patients on parenteral nutrition support. Clin Nutr. 2005 Jun;24(3):415-20. [15896428 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012362
KNApSAcK IDC00023770
Chemspider ID192962
KEGG Compound IDC01753
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhytosterol
NuGOwiki LinkHMDB00852
Metagene LinkHMDB00852
PubChem Compound222284
PDB IDNot Available
ChEBI ID27693
Synthesis ReferenceTrofimov, A. N.; Chuprova, V. A. Process for production of b-sitosterol from tall oil products. Khimiya Rastitel'nogo Syr'ya (2002), (2), 129-132.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [10758959 ]
  2. 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. [8253356 ]
  3. 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. [8028508 ]
  4. 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. [15824923 ]
  5. 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. [15867948 ]
  6. 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. [15989725 ]
  7. Ling WH, Jones PJ: Dietary phytosterols: a review of metabolism, benefits and side effects. Life Sci. 1995;57(3):195-206. [7596226 ]
  8. 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. [11240845 ]
  9. 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. [16477216 ]
  10. 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. [1499139 ]
  11. 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. [15893885 ]
  12. 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. [8429265 ]
  13. 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. [15816807 ]
  14. 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. [15726313 ]
  15. 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. [10695663 ]
  16. Bhattacharyya AK, Lopez LA: Absorbability of plant sterols and their distribution in rabbit tissues. Biochim Biophys Acta. 1979 Jul 27;574(1):146-53. [573140 ]
  17. 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. [10810360 ]
  18. 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. [15936608 ]
  19. 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. [14615068 ]
  20. 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. [15939057 ]


General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
Uniprot ID:
Molecular weight:
Avenasterol + NADPH + Hydrogen Ion → Beta-Sitosterol + NADPdetails