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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:08:51 UTC
Update Date2021-09-14 15:41:21 UTC
HMDB IDHMDB0012866
Secondary Accession Numbers
  • HMDB12866
Metabolite Identification
Common Name9'-Carboxy-alpha-chromanol
Description9'-carboxy-alpha-tocopherol is a dehydrogenation carboxylate product of 9'-hydroxy-a-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. The tocopherols ( a-tocopherol , b-tocopherol ,r-tocopherol and d-tocopherol ) and their corresponding tocotrienols are synthesized by plants and have vitamin E antixoidant activity (see pathway vitamin E biosynthesis ). They differ in the number and location of methyl groups on the chromanol ring. The naturally occurring form of a-tocopherol is (2R,4'R,8'R)-a-tocopherol (synonym (R,R,R)-a-tocopherol). Synthetic a-tocopherols are a racemic mixture of eight different R and S stereoisomers. Only the 2R forms are recognized as meeting human requirements. The in vivo function of vitamin E is to scavenge peroxyl radicals via its phenolic (chromanol) hydroxyl group, thus protecting lipids against free radical-catalyzed peroxidation. The tocopheryl radical formed can then be reduced by reductants such as L-ascorbate. Other major products of a-tocopherol oxidation include α-tocopherylquinone and epoxy-a-tocopherols. The metabolites a-tocopheronic acid and its lactone, known as the Simon metabolites, are generally believed to be artefacts. In addition to these oxidation products, the other major class of tocopherol metabolites is the carboxyethyl-hydroxychromans.These metabolites are produced in significant amounts in response to excess vitamin E ingestion. Vitamin E is fat-soluble and its utilization requires intestinal fat absorption mechanisms. It is secreted from the intestine into the lymphatic system in chylomicrons which subsequently enter the plasma. Lipolysis of these chylomicrons can result in delivery of vitamin E to tissues, transfer to high-density lipoproteins (and subsequently to other lipoproteins via the phospholipid exchange protein), or retention in chylomicron remnants. These remnants are taken up by the liver. Natural (R,R,R)-α-tocopherol and synthetic 2R-α-tocopherols are then preferentially secreted from the liver into plasma as a result of the specificity of the α-tocopherol transfer protein. This protein, along with the metabolism of excess vitamin E in the liver and excretion into urine and bile, mediate the supply of a-tocopherol in plasma and tissues.
Structure
Data?1582753075
Synonyms
ValueSource
9'-Carboxy-alpha-tocopherolHMDB
(6S)-9-[(2S)-6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnonanoateGenerator
Chemical FormulaC24H38O4
Average Molecular Weight390.5561
Monoisotopic Molecular Weight390.277009704
IUPAC Name(6S)-9-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid
Traditional Name(6S)-9-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid
CAS Registry NumberNot Available
SMILES
C[C@@H](CCCC(C)C(O)=O)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C
InChI Identifier
InChI=1S/C24H38O4/c1-15(9-7-11-16(2)23(26)27)10-8-13-24(6)14-12-20-19(5)21(25)17(3)18(4)22(20)28-24/h15-16,25H,7-14H2,1-6H3,(H,26,27)/t15-,16?,24-/m0/s1
InChI KeyCUGVBZDXUTZXJO-GCIQOJCMSA-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
  • Alkyl aryl ether
  • Branched fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.00058 g/LALOGPS
logP5.67ALOGPS
logP7.38ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)5ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity114.11 m³·mol⁻¹ChemAxon
Polarizability47.16 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.38231661259
DarkChem[M-H]-190.41831661259
DeepCCS[M+H]+199.78930932474
DeepCCS[M-H]-197.43130932474
DeepCCS[M-2H]-231.27530932474
DeepCCS[M+Na]+206.50330932474
AllCCS[M+H]+201.632859911
AllCCS[M+H-H2O]+199.232859911
AllCCS[M+NH4]+203.932859911
AllCCS[M+Na]+204.632859911
AllCCS[M-H]-204.732859911
AllCCS[M+Na-2H]-206.232859911
AllCCS[M+HCOO]-208.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
9'-Carboxy-alpha-chromanolC[C@@H](CCCC(C)C(O)=O)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C4268.8Standard polar33892256
9'-Carboxy-alpha-chromanolC[C@@H](CCCC(C)C(O)=O)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C2974.5Standard non polar33892256
9'-Carboxy-alpha-chromanolC[C@@H](CCCC(C)C(O)=O)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C3069.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
9'-Carboxy-alpha-chromanol,1TMS,isomer #1CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C)O2)C(C)=C1O2916.3Semi standard non polar33892256
9'-Carboxy-alpha-chromanol,1TMS,isomer #2CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCCC(C)C(=O)O)O2)C(C)=C1O[Si](C)(C)C2986.1Semi standard non polar33892256
9'-Carboxy-alpha-chromanol,2TMS,isomer #1CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C)O2)C(C)=C1O[Si](C)(C)C2958.8Semi standard non polar33892256
9'-Carboxy-alpha-chromanol,1TBDMS,isomer #1CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O3173.1Semi standard non polar33892256
9'-Carboxy-alpha-chromanol,1TBDMS,isomer #2CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCCC(C)C(=O)O)O2)C(C)=C1O[Si](C)(C)C(C)(C)C3237.2Semi standard non polar33892256
9'-Carboxy-alpha-chromanol,2TBDMS,isomer #1CC1=C(C)C2=C(CC[C@](C)(CCC[C@@H](C)CCCC(C)C(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O[Si](C)(C)C(C)(C)C3446.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 9'-Carboxy-alpha-chromanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-056v-4498000000-1a58e6e3c53fa88693072017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9'-Carboxy-alpha-chromanol GC-MS (2 TMS) - 70eV, Positivesplash10-01di-7278590000-3d1f22c3ebefa9b078202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9'-Carboxy-alpha-chromanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9'-Carboxy-alpha-chromanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 10V, Positive-QTOFsplash10-00r6-0419000000-1b909b2af5a45354471e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 20V, Positive-QTOFsplash10-014i-0911000000-7aa69e501c59a2d9b07b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 40V, Positive-QTOFsplash10-016r-1900000000-4d93f14c8f0d69b048f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 10V, Negative-QTOFsplash10-000i-0009000000-e4ce51bae06f0f67bcc02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 20V, Negative-QTOFsplash10-01pa-0319000000-034afebbf088626f17f72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 40V, Negative-QTOFsplash10-071j-3923000000-da0f980f1619f88b6f012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 10V, Negative-QTOFsplash10-000i-0009000000-7a0b01839255af1f268e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 20V, Negative-QTOFsplash10-00kp-0209000000-8e7780c46151dc97537a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 40V, Negative-QTOFsplash10-0a70-1393000000-f40ff2e44226a5bc0b862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 10V, Positive-QTOFsplash10-014m-0059000000-76cee7c90212b1d89f7c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 20V, Positive-QTOFsplash10-0002-1193000000-19f0e0d5a180283994c12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9'-Carboxy-alpha-chromanol 40V, Positive-QTOFsplash10-0a4i-5980000000-eae9b1d62f3097886e582021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029190
KNApSAcK IDNot Available
Chemspider ID35032551
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481534
PDB IDNot Available
ChEBI ID175124
Food Biomarker OntologyNot Available
VMH IDCE5856
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available