D-delta-Tocopherol (CHEM018881)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:37:27 UTC
Update Date2016-11-09 01:15:53 UTC
Accession NumberCHEM018881
Identification
Common NameD-delta-Tocopherol
ClassSmall Molecule
DescriptionA tocopherol in which the chroman-6-ol core is substituted by a methyl group at position 8. It is found particularly in maize (corn) oil and soya bean (soybean) oils.
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical 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 Mass402.653 g/mol
Monoisotopic Mass402.350 g/mol
CAS Registry Number119-13-1
IUPAC Name(2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Namedelta tocopherol
SMILESCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=CC(O)=C2
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.1e-05 g/LALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0ab9-3490300000-f13783678d446978a134Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ab9-3490300000-f13783678d446978a134Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0553-6966000000-24c590db65503bc92d19Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-7755900000-0db42dc49bee83a43b36Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udr-2500900000-d51c6b511d2655c65526Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0300900000-c7cd87c9e4b48f15bbbbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-0900000000-afcde4fb8f9be6edde67Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-0f79-3900300000-7367fe51787d1f4d6faeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0822900000-53573e0accb0cbdeedcdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1910000000-54f3075b09bc49ae07adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-5920000000-e8c787f9de39e1794e7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0100900000-ba38bc42ccadcfb32ed7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0801900000-295fe543769c50ae0fc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0914000000-ed731410a01607b11c51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3223900000-1d95ede1af4310b26021Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0571-9411100000-c28dcd02ad1cb1164263Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056v-9500000000-6d08cf1393844200bddeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-079f76b4d985e4b92c9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0900700000-1574fe7da8fc24170f5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ri-1903000000-6a9bc14f76db42f74276Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002902
FooDB IDFDB112209
Phenol Explorer IDNot Available
KNApSAcK IDC00007363
BiGG IDNot Available
BioCyc IDDELTA-TOCOPHEROL
METLIN ID232
PDB IDNot Available
Wikipedia LinkDelta-Tocopherol
Chemspider ID83144
ChEBI ID47772
PubChem Compound ID92094
Kegg Compound IDC14151
YMDB IDNot Available
ECMDB IDM2MDB005239
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10385606
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10419182
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11997390
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12600864
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12772433
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=14695946
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15544870
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=15596715
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15753140
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16384840
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=16400056
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=16457832
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=16614418
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=16876809
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=17203774
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=17927195
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=18356579
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=18811917
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=19443199
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=19454246
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=21815166
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=23636547
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=28203099
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=29746786
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=3630967
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=8245162
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=9706379
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33. Clarke MW, Ward NC, Wu JH, Hodgson JM, Puddey IB, Croft KD: Supplementation with mixed tocopherols increases serum and blood cell gamma-tocopherol but does not alter biomarkers of platelet activation in subjects with type 2 diabetes. Am J Clin Nutr. 2006 Jan;83(1):95-102.
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35. Liu M, Wallmon A, Olsson-Mortlock C, Wallin R, Saldeen T: Mixed tocopherols inhibit platelet aggregation in humans: potential mechanisms. Am J Clin Nutr. 2003 Mar;77(3):700-6.
36. Traber MG, Kayden HJ: Tocopherol distribution and intracellular localization in human adipose tissue. Am J Clin Nutr. 1987 Sep;46(3):488-95.
37. Gehring W, Fluhr J, Gloor M: Influence of vitamin E acetate on stratum corneum hydration. Arzneimittelforschung. 1998 Jul;48(7):772-5.
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39. Jiang Q, Wong J, Fyrst H, Saba JD, Ames BN: gamma-Tocopherol or combinations of vitamin E forms induce cell death in human prostate cancer cells by interrupting sphingolipid synthesis. Proc Natl Acad Sci U S A. 2004 Dec 21;101(51):17825-30. Epub 2004 Dec 13.
40. Sontag TJ, Parker RS: Cytochrome P450 omega-hydroxylase pathway of tocopherol catabolism. Novel mechanism of regulation of vitamin E status. J Biol Chem. 2002 Jul 12;277(28):25290-6. Epub 2002 May 7.
41. Epler KS, Ziegler RG, Craft NE: Liquid chromatographic method for the determination of carotenoids, retinoids and tocopherols in human serum and in food. J Chromatogr. 1993 Sep 8;619(1):37-48.
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43. Limpens J, Schroder FH, de Ridder CM, Bolder CA, Wildhagen MF, Obermuller-Jevic UC, Kramer K, van Weerden WM: Combined lycopene and vitamin E treatment suppresses the growth of PC-346C human prostate cancer cells in nude mice. J Nutr. 2006 May;136(5):1287-93.
44. Fischer CP, Hiscock NJ, Basu S, Vessby B, Kallner A, Sjoberg LB, Febbraio MA, Pedersen BK: Vitamin E isoform-specific inhibition of the exercise-induced heat shock protein 72 expression in humans. J Appl Physiol (1985). 2006 May;100(5):1679-87. Epub 2005 Dec 29.