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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-09-22 17:43:46 UTC
HMDB IDHMDB0001518
Secondary Accession Numbers
  • HMDB01518
Metabolite Identification
Common Namealpha-CEHC
Descriptionalpha-CEHC, also known as a-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 exists in all living organisms, ranging from bacteria to humans. alpha-CEHC has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and milk (cow). This could make alpha-cehc a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on alpha-CEHC.
Structure
Data?1582752207
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 Weight278.3435
Monoisotopic Molecular Weight278.151809192
IUPAC Name3-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoic acid
Traditional Nameα-cehc
CAS Registry Number4072-32-6
SMILES
CC1=C(O)C(C)=C2CCC(C)(CCC(O)=O)OC2=C1C
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.31531661259
DarkChem[M-H]-164.30231661259
AllCCS[M+H]+165.77832859911
AllCCS[M-H]-172.02732859911
DeepCCS[M+H]+164.36530932474
DeepCCS[M-H]-162.00630932474
DeepCCS[M-2H]-195.36930932474
DeepCCS[M+Na]+170.59530932474
AllCCS[M+H]+165.832859911
AllCCS[M+H-H2O]+162.332859911
AllCCS[M+NH4]+169.032859911
AllCCS[M+Na]+170.032859911
AllCCS[M-H]-172.032859911
AllCCS[M+Na-2H]-172.132859911
AllCCS[M+HCOO]-172.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-CEHCCC1=C(O)C(C)=C2CCC(C)(CCC(O)=O)OC2=C1C3585.3Standard polar33892256
alpha-CEHCCC1=C(O)C(C)=C2CCC(C)(CCC(O)=O)OC2=C1C2334.8Standard non polar33892256
alpha-CEHCCC1=C(O)C(C)=C2CCC(C)(CCC(O)=O)OC2=C1C2403.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-CEHC,1TMS,isomer #1CC1=C(C)C2=C(CCC(C)(CCC(=O)O)O2)C(C)=C1O[Si](C)(C)C2362.0Semi standard non polar33892256
alpha-CEHC,1TMS,isomer #2CC1=C(C)C2=C(CCC(C)(CCC(=O)O[Si](C)(C)C)O2)C(C)=C1O2286.2Semi standard non polar33892256
alpha-CEHC,2TMS,isomer #1CC1=C(C)C2=C(CCC(C)(CCC(=O)O[Si](C)(C)C)O2)C(C)=C1O[Si](C)(C)C2383.6Semi standard non polar33892256
alpha-CEHC,1TBDMS,isomer #1CC1=C(C)C2=C(CCC(C)(CCC(=O)O)O2)C(C)=C1O[Si](C)(C)C(C)(C)C2605.9Semi standard non polar33892256
alpha-CEHC,1TBDMS,isomer #2CC1=C(C)C2=C(CCC(C)(CCC(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O2547.4Semi standard non polar33892256
alpha-CEHC,2TBDMS,isomer #1CC1=C(C)C2=C(CCC(C)(CCC(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O[Si](C)(C)C(C)(C)C2817.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-CEHC GC-MS (Non-derivatized) - 70eV, Positivesplash10-08iu-4090000000-8ca9dbe51872599f76892017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-CEHC GC-MS (2 TMS) - 70eV, Positivesplash10-0ab9-9104300000-89eb4eb596d64c2632982017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-CEHC GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-CEHC GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-CEHC Linear Ion Trap , negative-QTOFsplash10-001i-0090000000-5984299071d9bd578a662017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-CEHC Linear Ion Trap , positive-QTOFsplash10-03di-0940000000-e94cb5537d42ecca8f252017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-CEHC 10V, Positive-QTOFsplash10-03di-0490000000-5a4d681fd73f355a60582015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-CEHC 20V, Positive-QTOFsplash10-014i-0930000000-b419f254c71bb6124ca12015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-CEHC 40V, Positive-QTOFsplash10-07br-2900000000-5c87bdb630cb5c9afc3e2015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-CEHC 10V, Negative-QTOFsplash10-004i-0190000000-eb3543747e604b52ab092015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-CEHC 20V, Negative-QTOFsplash10-0bw9-1490000000-1c600a1fe465c3eb79932015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-CEHC 40V, Negative-QTOFsplash10-0a4i-9810000000-c76ff537508835c548e22015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-CEHC 10V, Positive-QTOFsplash10-03di-0190000000-5a9a1904b542c448007a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-CEHC 20V, Positive-QTOFsplash10-03di-0790000000-0ce3fe0382fcea3030382021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-CEHC 40V, Positive-QTOFsplash10-00kb-7900000000-805173297214fa41fc0a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-CEHC 10V, Negative-QTOFsplash10-001i-0090000000-54b37056d244a02c63ec2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-CEHC 20V, Negative-QTOFsplash10-001i-0090000000-34fb2875b590a256850b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-CEHC 40V, Negative-QTOFsplash10-02tc-2490000000-b524618831ea011c0e2a2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.013 (0.0051-0.020) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022669
KNApSAcK IDNot Available
Chemspider ID8119154
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9943542
PDB IDNot Available
ChEBI ID626842
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferencePope, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:12420750 ]
  2. 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. [PubMed:11841923 ]
  3. 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. [PubMed:10552913 ]