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Showing metabocard for 13'-Hydroxy-alpha-tocopherol (HMDB12559)

Record Information
Version 3.5
Creation Date 2009-07-24 18:02:55 -0600
Update Date 2013-05-29 22:25:31 -0600
HMDB ID HMDB12559
Secondary Accession Numbers None
Metabolite Identification
Common Name 13'-Hydroxy-alpha-tocopherol
Description 13'-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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-(13-Hydroxy-4,8,12-trimethyltridecyl)-6-hydroxy-2,5,7,8-tetramethylchroman
Chemical Formula C29H50O3
Average Molecular Weight 446.7055
Monoisotopic Molecular Weight 446.375995466
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 IUPAC 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 Number Not 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 Key URYLCCKXLNXSRS-XIRVVSDESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Quinone and Hydroquinone Lipids
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Vitamin E
Substituents
  • Alkyl Aryl Ether
  • Benzopyran
  • Chromane
  • Diterpene
  • Farnesane Skeleton
  • Fatty Alcohol
  • M Cresol
  • O Cresol
  • Phenol
  • Phenol Derivative
  • Primary Alcohol
  • Pyran
  • Toluene
Direct Parent Tocopherols
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.700E-05 g/L ALOGPS
LogP 8.07 ALOGPS
LogP 9.15 ChemAxon
LogS -7.08 ALOGPS
pKa (strongest acidic) 10.8 ChemAxon
pKa (strongest basic) -1.7 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 49.69 A2 ChemAxon
Rotatable Bond Count 13 ChemAxon
Refractivity 137.23 ChemAxon
Polarizability 57.32 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029125
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12559 Link_out
Metagene Link HMDB12559 Link_out
METLIN ID Not Available
PubChem Compound 53481465 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available