Feruloyldihydro-beta-sitosterol (CHEM034261)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:47:21 UTC
Update Date2016-11-09 01:21:05 UTC
Accession NumberCHEM034261
Identification
Common NameFeruloyldihydro-beta-sitosterol
ClassSmall Molecule
DescriptionIsolated from maize bran oil. Feruloyldihydro-beta-sitosterol is found in cereals and cereal products and corn.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Feruloyldihydro-b-sitosterolGenerator
Feruloyldihydro-β-sitosterolGenerator
Sitostanol ferulateHMDB
Sitostanyl ferulateHMDB
Stigmastanol ferulateHMDB
(2S,5S,7S,14R,15R)-14-[(2R,5R)-5-Ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acidGenerator
Chemical FormulaC39H60O4
Average Molecular Mass592.891 g/mol
Monoisotopic Mass592.449 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S,5S,7S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Traditional Name(2S,5S,7S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
SMILESCC[C@@H](C(C)C)CC[C@@H](C)[C@H]1CCC2C3CC[C@H]4C[C@H](CC[C@]4(C)C3CC[C@]12C)OC(=O)\C=C\C1=CC(OC)=C(O)C=C1
InChI IdentifierInChI=1S/C39H60O4/c1-8-28(25(2)3)12-9-26(4)32-15-16-33-31-14-13-29-24-30(19-21-38(29,5)34(31)20-22-39(32,33)6)43-37(41)18-11-27-10-17-35(40)36(23-27)42-7/h10-11,17-18,23,25-26,28-34,40H,8-9,12-16,19-22,24H2,1-7H3/b18-11+/t26-,28-,29+,30+,31?,32-,33?,34?,38+,39-/m1/s1
InChI KeyRAKOKKNCCBUUMP-OCZIXQBLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • C24-propyl-sterol-skeleton
  • Triterpenoid
  • Steroid ester
  • Steroid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Styrene
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Ether
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
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 Solubility4.4e-06 g/LALOGPS
logP8.26ALOGPS
logP10.82ChemAxon
logS-8.1ALOGPS
pKa (Strongest Acidic)9.87ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity176.93 m³·mol⁻¹ChemAxon
Polarizability73.92 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ta-4408190000-2e2da2c4b8ad6bd78017Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-4126019000-c03f88668128d79ad4c1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Feruloyldihydro-beta-sitosterol,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0702390000-fdfc5873eaffbe6b8edbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-3905220000-7dc415949a95de209cdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-5519120000-498a9082799ac3587051Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0100390000-3c390d2d8238efcd6e5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0601930000-834c99ffdc7d76beea3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-2509800000-5471ca5d5324053c1a5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000190000-474fe9dc9b1ebf7226f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-007c-0900240000-e82e07d8808a79e7767dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001s-0900120000-cf619462c41224a4a7d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r6-0202290000-9ab470a3e93b4d6a0610Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-074u-5224490000-960201e17ef74072e2d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-5923110000-6ed2facfa868624d36d6Spectrum
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 IDHMDB0041128
FooDB IDFDB021010
Phenol Explorer ID566
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID131753037
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Norton RA: Quantitation of steryl ferulate and p-coumarate esters from corn and rice. Lipids. 1995 Mar;30(3):269-74.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
7. The lipid handbook with CD-ROM