beta-Tocopherol (CHEM028227)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:18:27 UTC
Update Date2016-11-09 01:18:38 UTC
Accession NumberCHEM028227
Identification
Common Namebeta-Tocopherol
ClassSmall Molecule
DescriptionA tocopherol in which the chroman-6-ol core is substituted by methyl groups at positions 5 and 8. While it is found in low concentrations in many vegetable oils, only cottonseed oil contains significant amounts.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2R)-2,5,8-Trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-olChEBI
(2R)-3,4-Dihydro-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-olChEBI
(2R,4'r,8'r)-beta-TocopherolChEBI
(R,R,R)-beta-TocopherolChEBI
5,8-DimethyltocolChEBI
RRR-beta-TocopherolChEBI
(2R,4'r,8'r)-b-TocopherolGenerator
(2R,4'r,8'r)-Β-tocopherolGenerator
(R,R,R)-b-TocopherolGenerator
(R,R,R)-Β-tocopherolGenerator
RRR-b-TocopherolGenerator
RRR-Β-tocopherolGenerator
b-TocopherolGenerator
Β-tocopherolGenerator
beta TocopherolHMDB
3,4-Dihydro-2,5,8-trimethyl-2-(4,8,12- trimethyltridecyl)-2H-1-benzopyran-6-olHMDB
b-Tocopherol skeletonHMDB
Β-tocopherol skeletonHMDB
CumotocopherolHMDB
DL-beta-TocopherolHMDB
DL-Β-tocopherolHMDB
NeotocopherolHMDB
p-XylotocopherolHMDB
beta-TocopherolMeSH
2,5,8-Trimethyl-2-(4,8,12-trimethyltridecyl)-6-chromanolHMDB
Chemical FormulaC28H48O2
Average Molecular Mass416.680 g/mol
Monoisotopic Mass416.365 g/mol
CAS Registry Number16698-35-4
IUPAC Name(2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Nameβ-tocopherol
SMILESCC(C)CCCC(C)CCCC(C)CCCC1(C)CCC2=C(C)C(O)=CC(C)=C2O1
InChI IdentifierInChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-24(6)26(29)19-23(5)27(25)30-28/h19-22,29H,8-18H2,1-7H3
InChI KeyWGVKWNUPNGFDFJ-UHFFFAOYSA-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 Solubility7.3e-06 g/LALOGPS
logP8.81ALOGPS
logP9.99ChemAxon
logS-7.8ALOGPS
pKa (Strongest Acidic)10.47ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity130.33 m³·mol⁻¹ChemAxon
Polarizability53.32 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)splash10-00di-1490200000-f75de727e16d87c65fbaSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-1490200000-f75de727e16d87c65fbaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0lyo-6954200000-ffcf92e6a6e2f34dd922Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5644900000-b5341f1bdc151c1a796bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-0gb9-3900600000-10f458ddcb7e7aa4df84Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-0f6t-0900600000-9a11a437c645252a72a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0842900000-82c505b0548997aace83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1910000000-1b1a0fe2f352daa49e2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-4920000000-b63881a7743c06bdea15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0100900000-2345f13b44d6c70d81e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0912800000-4e68210f69fcd3f6c374Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kk-0914000000-f6f5255b874c4fc7f4f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-a74b65a822c3cc7625b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0201900000-2dcdf4f502cc6e57342dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-024m-2913100000-fb9e3e53715df460db95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3113900000-16d3b372ee248c26f313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-9213100000-65be5213a11752835e85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052g-9400000000-947da441c6df0de93bedSpectrum
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 IDHMDB0006335
FooDB IDFDB012381
Phenol Explorer IDNot Available
KNApSAcK IDC00007364
BiGG ID2296531
BioCyc IDBETA-TOCOPHEROL
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBeta-Tocopherol
Chemspider ID5256784
ChEBI ID47771
PubChem Compound ID6857447
Kegg Compound IDC14152
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11390183
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16746572
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16771430
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19339706
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19710160
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19717743
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20357932
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22168240
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23997325
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=262184
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=27694009
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=5158483
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=9043639
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=9920007
15.
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18.
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=PMC7258573
20. John, Walter. Cumotocopherol, a new factor of the vitamin-E group. Z. physiol. Chem. (1937), 250 11-24. CAN 32:8751 AN 1938:8751
21. John, Walter. Cumotocopherol, a new factor of the vitamin-E group. Z. physiol. Chem. (1937), 250 11-24. CAN 32:8751 AN 1938:8751
22. Wilson GJ, Lin CY, Webster RD: Significant differences in the electrochemical behavior of the alpha-, beta-, gamma-, and delta-tocopherols (vitamin E). J Phys Chem B. 2006 Jun 15;110(23):11540-8.
23. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.