Showing metabocard for Delta-Tocopherol (BMDB0002902)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:02:05 UTC
Update Date2020-06-04 19:00:11 UTC
MCDB ID BMDB0002902
Secondary Accession Numbers
  • BMDB02902
Metabolite Identification
Common NameDelta-Tocopherol
DescriptionDelta-Tocopherol, also known as 8-methyltocol or δ-tocopherol, 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. Thus, Delta-tocopherol is considered to be a quinone lipid molecule. Delta-Tocopherol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Delta-Tocopherol exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-delta-TocopherolChEBI
(2R)-2,8-Dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-olChEBI
(2R)-3,4-Dihydro-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-olChEBI
(2R,4'r,8'r)-delta-TocopherolChEBI
(R,R,R)-delta-TocopherolChEBI
8-MethyltocolChEBI
e309ChEBI
RRR-delta-TocopherolChEBI
(+)-Δ-tocopherolGenerator
(2R,4'r,8'r)-Δ-tocopherolGenerator
(R,R,R)-Δ-tocopherolGenerator
RRR-Δ-tocopherolGenerator
Δ-tocopherolGenerator
Vitamine eHMDB
(2R,4’R,8’r)-δ-tocopherolHMDB
D-delta-TocopherolHMDB
D-Δ-tocopherolHMDB
delta-D-TocopherolHMDB
delta-Vitamin eHMDB
Δ-D-tocopherolHMDB
Δ-vitamin eHMDB
delta-TocopherolHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Namedelta tocopherol
CAS Registry Number119-13-1
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=CC(O)=C2
InChI Identifier
InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h18-22,28H,7-17H2,1-6H3/t21-,22-,27-/m1/s1
InChI KeyGZIFEOYASATJEH-VHFRWLAGSA-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
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.76ALOGPS
logP9.48ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)10.14ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity125.29 m³·mol⁻¹ChemAxon
Polarizability51.31 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0ab9-3490300000-f13783678d446978a1342014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ab9-3490300000-f13783678d446978a1342017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0553-6966000000-24c590db65503bc92d192017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-7755900000-0db42dc49bee83a43b362017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udr-2500900000-d51c6b511d2655c655262012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0300900000-c7cd87c9e4b48f15bbbb2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-0900000000-afcde4fb8f9be6edde672012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-0f79-3900300000-7367fe51787d1f4d6fae2012-08-31View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0822900000-53573e0accb0cbdeedcd2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1910000000-54f3075b09bc49ae07ad2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-5920000000-e8c787f9de39e1794e7c2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0100900000-ba38bc42ccadcfb32ed72017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0801900000-295fe543769c50ae0fc42017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0914000000-ed731410a01607b11c512017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3223900000-1d95ede1af4310b260212021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0571-9411100000-c28dcd02ad1cb11642632021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056v-9500000000-6d08cf1393844200bdde2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-079f76b4d985e4b92c9d2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0900700000-1574fe7da8fc24170f5d2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ri-1903000000-6a9bc14f76db42f742762021-09-24View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.002 +/- 0.002 uM
  • International Dai...
 details
Detected and Quantified0.01 +/- 0.003 uM
  • International Dai...
 details
HMDB IDHMDB0002902
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112209
KNApSAcK IDC00007363
Chemspider ID83144
KEGG Compound IDC14151
BioCyc IDDELTA-TOCOPHEROL
BiGG IDNot Available
Wikipedia LinkDelta-Tocopherol
METLIN ID232
PubChem Compound92094
PDB IDNot Available
ChEBI ID47772
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. M.S Havemose, Martin Riis Weisbjerg, Wender L.P Bredie, J.H Nielsen (2004). International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570. International Dairy Journal.