Record Information
Creation date2015-10-09 22:28:01 UTC
Update date2017-01-19 02:36:12 UTC
FoodComEx IDPC000077
FoodDB RecordFDB001936
Chemical Information
DescriptionStigmasterol, also known as poriferasterol or phytosterol, 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. Stigmasterol is a phytosterol, meaning it is steroid derived from plants. ,It is very hydrophobic, practically insoluble in water, and relatively neutral. Stigmasterol is among the most abundant of plant sterols with its major function being to maintain the structure and physiology of cell membranes. It is found in plant fats or oils associated with various vegetables, legumes, nuts, and seeds such as soybean, calabar bean, rape seed and various herbs. Stigmasterol is also a constituent of unpasteurized milk. Pasteurization is known to inactivate stigmasterol. Stigmasterol is a food additive in manufactured food products in the United Kingdom and European Union. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Consumption of 2 grams per day of plant sterols is associated with a reduction in blood LDL cholesterol of 8-10% (PMID: 29267628). As the typical western diet contains only about 300 mg/day of phytosterols, foods enriched with phytosterols are usually used to achieve the recommended intake (PMID: 29267628). The mechanism behind phytosterols lowering cholesterol involves the inhibition of the incorporation of cholesterol into micelles in the gastrointestinal tract, which decreases the overall amount of cholesterol absorbed. This may in turn help to control body total plasma cholesterol levels, as well as modify HDL, LDL and TAG levels in blood. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people wishing to lower their cholesterol levels. More recently, stigmasterol has been identified as a potent and independent risk factor for cardiovascular disease. Accumulation of stigmasterol leads to left ventricle dysfunction, cardiac interstitial fibrosis and macrophage infiltration without atherosclerosis (PMID: 30675518). Stigmasterol has been found to be associated with phytosterolemia, a disease characterized by elevated levels of dietary plant sterols in the blood. (PMID: 30675518).
CAS Number83-48-7
Stigmasta-5,22-dien-3-ol, (3β,22E)-biospider
Stigmasta-5,22-dien-3-ol, (3β)-biospider
Stigmasta-5,22-dien-3-ol, (3beta,22E)- (9CI)biospider
Stigmasta-5,22-dien-3-ol, (3beta)-biospider
Stigmasta-5,22-dien-3beta-ol (8CI)biospider
Chemical FormulaC29H48O
IUPAC name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[^{2,7}.0^{11,15}]heptadec-7-en-5-ol
InChI IdentifierInChI=1S/C29H48O/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/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
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)\C=C\[C@@H](CC)C(C)C
Average Molecular Weight412.702
Monoisotopic Molecular Weight412.370516166
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
  • 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
Physico-Chemical Properties - Experimental
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointMp 170°DFC
Foods of Origin
FoodContent Range AverageReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 2 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez
Commercial Vendors
AKSci P501
AKSci HMDB0000937
Cayman Chemical 18079
Glentham GP9119
Glentham GP5909
MetaSci HMDB0000937
Toronto Research Chemicals S686750