alpha-CEHC (CHEM035253)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:36:36 UTC
Update Date2016-11-09 01:21:16 UTC
Accession NumberCHEM035253
Identification
Common Namealpha-CEHC
ClassSmall Molecule
DescriptionAlpha-Cehc, also known as Α-cehc, 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. Alpha-Cehc is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Alpha-Cehc exists in all living organisms, ranging from bacteria to humans.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
a-CEHCGenerator
Α-cehcGenerator
3-(6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoateHMDB
α-Carboxyethyl hydrochromanHMDB
alpha-Carboxyethyl hydrochromanGenerator
2,5,7,8-Tetramethyl-2(2'-carboxyethyl)-6-hydroxychromanHMDB
2,5,7,8-Tetramethyl-2-(β-carboxyethyl)-6-hydroxychromanGenerator
2,5,7,8-Tetramethyl-2-(beta-carboxyethyl)-6-hydroxychromanHMDB
6-Hydroxy-2-(2-carboxylethyl)-2,5,7,8-tetramethylchromanHMDB
6-Hydroxy-2-carboxylethyl-2,5,7,8-tetramethylchromanHMDB
alpha-CEHCMeSH
Chemical FormulaC16H22O4
Average Molecular Mass278.344 g/mol
Monoisotopic Mass278.152 g/mol
CAS Registry Number4072-32-6
IUPAC Name3-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoic acid
Traditional Nameα-cehc
SMILESCC1=C(C)C2=C(CCC(C)(CCC(O)=O)O2)C(C)=C1O
InChI IdentifierInChI=1S/C16H22O4/c1-9-10(2)15-12(11(3)14(9)19)5-7-16(4,20-15)8-6-13(17)18/h19H,5-8H2,1-4H3,(H,17,18)
InChI KeyAXODOWFEFKOVSH-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 Solubility0.21 g/LALOGPS
logP2.9ALOGPS
logP3.88ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)4.4ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity77.38 m³·mol⁻¹ChemAxon
Polarizability30.5 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, Positivesplash10-08iu-4090000000-8ca9dbe51872599f7689Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0ab9-9104300000-89eb4eb596d64c263298Spectrum
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 - Linear Ion Trap , negativesplash10-001i-0090000000-5984299071d9bd578a66Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0940000000-e94cb5537d42ecca8f25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0490000000-5a4d681fd73f355a6058Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0930000000-b419f254c71bb6124ca1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07br-2900000000-5c87bdb630cb5c9afc3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-eb3543747e604b52ab09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bw9-1490000000-1c600a1fe465c3eb7993Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9810000000-c76ff537508835c548e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-5a9a1904b542c448007aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0790000000-0ce3fe0382fcea303038Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-7900000000-805173297214fa41fc0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-54b37056d244a02c63ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-34fb2875b590a256850bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02tc-2490000000-b524618831ea011c0e2aSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDHMDB0001518
FooDB IDFDB022669
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8119154
ChEBI ID626842
PubChem Compound ID9943542
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDECMDB24070
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.
2. Pope, Simon A. S.; Burtin, Guillaume E.; Clayton, Peter T.; Madge, David J.; Muller, David P. R. Synthesis and analysis of conjugates of the major vitamin E metabolite, a-CEHC. Free Radical Biology & Medicine (2002), 33(6), 807-817.
3. Betancor-Fernandez A, Sies H, Stahl W, Polidori MC: In vitro antioxidant activity of 2,5,7,8-tetramethyl-2-(2'-carboxyethyl)-6-hydroxychroman (alpha-CEHC), a vitamin E metabolite. Free Radic Res. 2002 Aug;36(8):915-21.
4. Galli F, Lee R, Dunster C, Kelly FJ: Gas chromatography mass spectrometry analysis of carboxyethyl-hydroxychroman metabolites of alpha- and gamma-tocopherol in human plasma. Free Radic Biol Med. 2002 Feb 15;32(4):333-40.
5. Stahl W, Graf P, Brigelius-Flohe R, Wechter W, Sies H: Quantification of the alpha- and gamma-tocopherol metabolites 2,5,7, 8-tetramethyl-2-(2'-carboxyethyl)-6-hydroxychroman and 2,7, 8-trimethyl-2-(2'-carboxyethyl)-6-hydroxychroman in human serum. Anal Biochem. 1999 Nov 15;275(2):254-9.