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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:02:55 UTC
Update Date2022-03-07 02:51:26 UTC
HMDB IDHMDB0012559
Secondary Accession Numbers
  • HMDB12559
Metabolite Identification
Common Name13'-Hydroxy-alpha-tocopherol
Description13'-hydroxy-alpha-tocopherol is the precursor in dehydrogenation to 13'-carboxy-alpha-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?1582753064
Synonyms
ValueSource
13-OH-alpha-TocopherolChEBI
13-OH-a-TocopherolGenerator
13-OH-Α-tocopherolGenerator
13'-Hydroxy-a-tocopherolGenerator
13'-Hydroxy-α-tocopherolGenerator
13-Hydroxy-a-tocopherolHMDB
13-Hydroxy-α-tocopherolHMDB
13'-Hydroxy-alpha-tocopherolChEBI
Chemical FormulaC29H50O3
Average Molecular Weight446.7055
Monoisotopic Molecular Weight446.375995466
IUPAC Name(2R)-2-[(4R,8S)-13-hydroxy-4,8,12-trimethyltridecyl]-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Name(2R)-2-[(4R,8S)-13-hydroxy-4,8,12-trimethyltridecyl]-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-6-ol
CAS Registry NumberNot Available
SMILES
CC(CO)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C
InChI Identifier
InChI=1S/C29H50O3/c1-20(13-9-14-22(3)19-30)11-8-12-21(2)15-10-17-29(7)18-16-26-25(6)27(31)23(4)24(5)28(26)32-29/h20-22,30-31H,8-19H2,1-7H3/t20-,21+,22?,29+/m0/s1
InChI KeyURYLCCKXLNXSRS-XIRVVSDESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentTocopherols
Alternative Parents
Substituents
  • Tocopherol
  • Diterpenoid
  • Long chain fatty alcohol
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Fatty alcohol
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
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 Solubility3.7e-05 g/LALOGPS
logP8.07ALOGPS
logP9.15ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)10.8ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity137.23 m³·mol⁻¹ChemAxon
Polarizability57.32 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
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]+210.68431661259
DarkChem[M-H]-204.51931661259
DeepCCS[M+H]+215.47530932474
DeepCCS[M-H]-213.0830932474
DeepCCS[M-2H]-245.96230932474
DeepCCS[M+Na]+221.38830932474
AllCCS[M+H]+217.232859911
AllCCS[M+H-H2O]+215.332859911
AllCCS[M+NH4]+219.032859911
AllCCS[M+Na]+219.532859911
AllCCS[M-H]-216.632859911
AllCCS[M+Na-2H]-219.732859911
AllCCS[M+HCOO]-223.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
13'-Hydroxy-alpha-tocopherolCC(CO)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C4095.5Standard polar33892256
13'-Hydroxy-alpha-tocopherolCC(CO)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C3368.6Standard non polar33892256
13'-Hydroxy-alpha-tocopherolCC(CO)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C3462.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
13'-Hydroxy-alpha-tocopherol,1TMS,isomer #1CC1=C(C)C2=C(CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)CO[Si](C)(C)C)O2)C(C)=C1O3275.7Semi standard non polar33892256
13'-Hydroxy-alpha-tocopherol,1TMS,isomer #2CC1=C(C)C2=C(CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)CO)O2)C(C)=C1O[Si](C)(C)C3348.7Semi standard non polar33892256
13'-Hydroxy-alpha-tocopherol,2TMS,isomer #1CC1=C(C)C2=C(CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)CO[Si](C)(C)C)O2)C(C)=C1O[Si](C)(C)C3304.9Semi standard non polar33892256
13'-Hydroxy-alpha-tocopherol,1TBDMS,isomer #1CC1=C(C)C2=C(CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)CO[Si](C)(C)C(C)(C)C)O2)C(C)=C1O3535.0Semi standard non polar33892256
13'-Hydroxy-alpha-tocopherol,1TBDMS,isomer #2CC1=C(C)C2=C(CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)CO)O2)C(C)=C1O[Si](C)(C)C(C)(C)C3606.9Semi standard non polar33892256
13'-Hydroxy-alpha-tocopherol,2TBDMS,isomer #1CC1=C(C)C2=C(CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)CO[Si](C)(C)C(C)(C)C)O2)C(C)=C1O[Si](C)(C)C(C)(C)C3808.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 13'-Hydroxy-alpha-tocopherol GC-MS (Non-derivatized) - 70eV, Positivesplash10-05pk-2796500000-696d167e7dff626a28562017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13'-Hydroxy-alpha-tocopherol GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2445390000-69dfb80c7cbe0f4cc3d92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13'-Hydroxy-alpha-tocopherol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13'-Hydroxy-alpha-tocopherol 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 - 13'-Hydroxy-alpha-tocopherol 10V, Positive-QTOFsplash10-00mk-0421900000-c2e2838b4fed1944830b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 20V, Positive-QTOFsplash10-014i-0910100000-ae48ef0eac05453a364a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 40V, Positive-QTOFsplash10-014i-1910000000-cac243bd70399ac13a772017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 10V, Negative-QTOFsplash10-0002-0000900000-e8a490fcd22573d720022017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 20V, Negative-QTOFsplash10-01ot-0410900000-2df09762b86f7f4ffb1d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 40V, Negative-QTOFsplash10-0gwb-0923300000-2fb95536d042c7aef0a72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 10V, Positive-QTOFsplash10-0002-2115900000-099be936055d32b60bb02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 20V, Positive-QTOFsplash10-014j-6729200000-ecfbf5f04269af7045d02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 40V, Positive-QTOFsplash10-0aor-9532000000-a1c54a6c597c9eeed41e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 10V, Negative-QTOFsplash10-002b-0000900000-fce93c2306a34f832c4f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 20V, Negative-QTOFsplash10-02ta-0411900000-a8a991079c3018f0635c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13'-Hydroxy-alpha-tocopherol 40V, Negative-QTOFsplash10-0bvi-0469700000-7a2f459658cb79c8561c2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB029125
KNApSAcK IDNot Available
Chemspider ID34999549
KEGG Compound IDNot Available
BioCyc IDCPD-11960
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481465
PDB IDNot Available
ChEBI ID84962
Food Biomarker OntologyNot Available
VMH IDCE5842
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.