3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid (CHEM032148)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:10:30 UTC
Update Date2016-11-09 01:19:24 UTC
Accession NumberCHEM032148
Identification
Common Name3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid
ClassSmall Molecule
DescriptionA chromanol that is 6-hydroxychromane which is substituted by a carboxy group at position 2 and by methyl groups at positions 2, 5, 7, and 8. A cell-permeable, water-soluble analogue of vitamin E, it is used as a standard for measuring the antioxidant capacity of complex mixtures.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acidChEBI
Trolox CChEBI
6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylateGenerator
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylateGenerator
TroloxHMDB
Trolox(TM)HMDB
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acidChEBI
6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carboxylic acidMeSH
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2- carboxylic acidMeSH
(+--)-TroloxMeSH
Chemical FormulaC14H18O4
Average Molecular Mass250.290 g/mol
Monoisotopic Mass250.121 g/mol
CAS Registry Number56305-04-5
IUPAC Name6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid
Traditional Nametrolox
SMILESCC1=C(O)C(C)=C2CCC(C)(OC2=C1C)C(O)=O
InChI IdentifierInChI=1S/C14H18O4/c1-7-8(2)12-10(9(3)11(7)15)5-6-14(4,18-12)13(16)17/h15H,5-6H2,1-4H3,(H,16,17)
InChI KeyGLEVLJDDWXEYCO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent1-benzopyrans
Alternative Parents
Substituents
  • 1-benzopyran
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.38 g/LALOGPS
logP2.75ALOGPS
logP3.66ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity68.08 m³·mol⁻¹ChemAxon
Polarizability26.94 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nml-1790000000-34dbaaa9d2d537ea683cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-9125000000-c355b1eafb56448742b0Spectrum
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-066r-1910000000-d3110bbdbf84bfc4a51aSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-066r-1910000000-d3110bbdbf84bfc4a51aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0970000000-6d332fcae90355a38722Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0o7i-1950000000-e9a6dccef7c156db25ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-1900000000-dbf2f9ed4cf23ec2fa22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-8d9e92e3b8dbc69e9384Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-0290000000-27b5e1cc9a996f954b5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-1900000000-68b68f1c88d2469ed89aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-18320cb565cfb33802eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0190000000-8e5dd5c019e57ddfbe1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-2900000000-c87b3764a772e98228f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0190000000-2e81bd608e8c504411e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0rki-1940000000-9838ee98efbe94a73dfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9800000000-023a301f5823935c0e1dSpectrum
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 IDHMDB0038804
FooDB IDFDB018229
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTrolox
Chemspider ID37117
ChEBI ID82625
PubChem Compound ID40634
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1459482
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17509231
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22096330
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22148238
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24362491
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24587218
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24605086
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24768628
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24885253
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24929117
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=31293030
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=32595071
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=33137938
14. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.