5'-Carboxy-gamma-chromanol (CHEM040998)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:07:41 UTC
Update Date2016-11-09 01:22:22 UTC
Accession NumberCHEM040998
Identification
Common Name5'-Carboxy-gamma-chromanol
ClassSmall Molecule
Description5'-Carboxy-gamma-tocopherol is a dehydrogenation carboxylate product of 5'-hydroxy-r-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. r-Tocopherol provides different antioxidant activities in food and in-vitro studies and showed higher activity in trapping lipophilic electrophiles and reactive nitrogen and oxygen species. From the metabolism end product, only that of r-tocopherol (2,7,8-trimethyl-2-(b-carboxyethyl)-6-hydroxychroman), but not that of a-tocopherol, was identified to provide natriuretic activity. Only the r-tocopherol plasma level served as biomarker for cancer and cardiovascular risk.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2S)-5-[(2R)-6-Hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2-methylpentanoateHMDB
Γ-CMBHCHMDB
gamma-CMBHCHMDB
γ-Carboxymethylbutyl hydroxychromanHMDB
γ-CarboxymethylbutylhydroxychromanHMDB
gamma-Carboxymethylbutyl hydroxychromanHMDB
gamma-CarboxymethylbutylhydroxychromanHMDB
Chemical FormulaC18H26O4
Average Molecular Mass306.397 g/mol
Monoisotopic Mass306.183 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S)-5-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2-methylpentanoic acid
Traditional Name(2S)-5-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-2-methylpentanoic acid
SMILESC[C@H](CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2)C(O)=O
InChI IdentifierInChI=1S/C18H26O4/c1-11(17(20)21)6-5-8-18(4)9-7-14-10-15(19)12(2)13(3)16(14)22-18/h10-11,19H,5-9H2,1-4H3,(H,20,21)/t11-,18-/m1/s1
InChI KeyCNGKBUHOCIWLHJ-ADLMAVQZSA-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
  • Medium-chain fatty acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Branched fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.033 g/LALOGPS
logP3.92ALOGPS
logP4.8ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.27ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity86.12 m³·mol⁻¹ChemAxon
Polarizability35.02 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, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pbi-0795000000-2a760615a1137de9e063Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1920000000-0b6e86db1ccc007ae9aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-5900000000-a1641967f03e449c84aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0129000000-ca2b2a47f99db6cbbdcfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bta-1895000000-31aed0c986eda055c878Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-7970000000-84306781d9a92ffbebffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-f8a5e82e8af4d5edf5e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0lxt-1974000000-2e3c70bb39be5f027e99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006w-0940000000-16b1c3ee83486876f9afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08g0-0192000000-c340a46203f3dd7a4c1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06xx-2290000000-f0e4037b879a4f1c1eb1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvu-6900000000-6fcdce7d23a6a930918aSpectrum
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 IDHMDB0012799
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID74854293
ChEBI IDNot Available
PubChem Compound ID134159052
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Birringer M, Pfluger P, Kluth D, Landes N, Brigelius-Flohe R: Identities and differences in the metabolism of tocotrienols and tocopherols in HepG2 cells. J Nutr. 2002 Oct;132(10):3113-8.
2. Zhao Y, Lee MJ, Cheung C, Ju JH, Chen YK, Liu B, Hu LQ, Yang CS: Analysis of multiple metabolites of tocopherols and tocotrienols in mice and humans. J Agric Food Chem. 2010 Apr 28;58(8):4844-52. doi: 10.1021/jf904464u.