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Stigmasterol (FDB001936)

Record Information
Version1.0
Creation date2010-04-08 22:05:10 UTC
Update date2020-09-17 15:42:30 UTC
Primary IDFDB001936
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameStigmasterol
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
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.7e-05 g/LALOGPS
logP6.95ALOGPS
logP7.48ChemAxon
logS-7.2ALOGPS
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 Count5ChemAxon
Refractivity130.88 m³·mol⁻¹ChemAxon
Polarizability53.55 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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[8.7.0.0^{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
InChI KeyHCXVJBMSMIARIN-PHZDYDNGSA-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)\C=C\[C@@H](CC)C(C)C
Average Molecular Weight412.702
Monoisotopic Molecular Weight412.370516166
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 84.40%; H 11.72%; O 3.88%DFC
Melting PointMp 170°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D -57 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a59-8920000000-c7d02c3957677fae28be2015-03-01View Spectrum
GC-MSStigmasterol, non-derivatized, GC-MS Spectrumsplash10-0a4i-3941000000-4b20188a87c1dadeae49Spectrum
GC-MSStigmasterol, non-derivatized, GC-MS Spectrumsplash10-0a59-9720000000-02211a4df6ec5c313295Spectrum
GC-MSStigmasterol, non-derivatized, GC-MS Spectrumsplash10-053r-7941000000-7983b2cb8a74cfda7530Spectrum
GC-MSStigmasterol, non-derivatized, GC-MS Spectrumsplash10-0a59-9731000000-168578ccead65322e450Spectrum
GC-MSStigmasterol, non-derivatized, GC-MS Spectrumsplash10-0a4i-3941000000-4b20188a87c1dadeae49Spectrum
GC-MSStigmasterol, non-derivatized, GC-MS Spectrumsplash10-0a59-9720000000-02211a4df6ec5c313295Spectrum
GC-MSStigmasterol, non-derivatized, GC-MS Spectrumsplash10-053r-7941000000-7983b2cb8a74cfda7530Spectrum
GC-MSStigmasterol, non-derivatized, GC-MS Spectrumsplash10-0a59-9731000000-168578ccead65322e450Spectrum
Predicted GC-MSStigmasterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001j-1109000000-be897608aaeab74e5d13Spectrum
Predicted GC-MSStigmasterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0avl-2102900000-564b610342ad160ee822Spectrum
Predicted GC-MSStigmasterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSStigmasterol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-03di-0000900000-f7738a3fcdee344f82c92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-07cs-9400200000-959314bea26c5acd83012012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0a59-7900000000-ce066e558ecbe29afea82012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positivesplash10-0a4i-3941000000-f854893a9352ff7667342012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0a59-9720000000-5a3d902c3cd2af078da32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-053r-7941000000-6c5c63e8c487f86b353b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-0a59-9731000000-32a70fa14fd448314caa2012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-2019500000-3495ed3a1955cc77528a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9128100000-3c3b91bb2d698a88f9db2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-8197000000-a80e8fcc32cd4a2dfefe2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-322cae85ce921a9ef9e22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0004900000-d25be97b0cfa1b9bed792017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-2019000000-3b119d03e184f575cdc42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xr-2219400000-9acb072e76ff1b8f2e482021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-7259000000-a7f52c0e28b61ef2a3ac2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9320000000-8a54eac3182f86b7095b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-363450e12a0ea926276e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0001900000-fe3ab0b12c2d51198ed02021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1001900000-43dce6fa5af31f5d79582021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC05442
Pubchem Compound ID5280794
Pubchem Substance IDNot Available
ChEBI ID28824
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00937
CRC / DFC (Dictionary of Food Compounds) IDHKT95-L:CBG86-I
EAFUS IDNot Available
Dr. Duke IDSTIGMASTEROL
BIGG IDNot Available
KNApSAcK IDC00023774
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDStigmasterol
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
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti nociceptive35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
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 viral22587 A substance that destroys or inhibits replication of viruses.DUKE
artemicideDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
estrogenicDUKE
hypocholesterolemicDUKE
ovulantDUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
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.