13'-Hydroxy-alpha-tocotrienol (CHEM040949)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:05:29 UTC
Update Date2016-11-09 01:22:21 UTC
Accession NumberCHEM040949
Identification
Common Name13'-Hydroxy-alpha-tocotrienol
ClassSmall Molecule
Description13'-hydroxy-a-tocotrienol is the precursor of dehydrogenation to 13'-carboxy-alpha-tocotrienol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. Tocotrienols are members of the vitamin E family. An essential nutrient for the body, vitamin E is made up of four tocopherols (alpha, beta, gamma, delta) and four tocotrienols (alpha, beta, gamma, delta).Chemically, vitamin E is an antioxidant. One model for the function of vitamin E in the body is that it protects cell membranes, active enzyme sites, and DNA from free radical damage. Tocotrienols are natural compounds found in select vegetable oils, wheat germ, barley, saw palmetto, and certain types of nuts and grains. This variant of vitamin E only occur at very low levels in nature. While the majority of research on vitamin E has focused on alpha-tocopherol, studies into tocotrienols account for less than 1% of all research into vitamin E.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
13'-Hydroxy-a-tocotrienolGenerator
13'-Hydroxy-α-tocotrienolGenerator
13ohaTEHMDB
Chemical FormulaC29H44O3
Average Molecular Mass440.658 g/mol
Monoisotopic Mass440.329 g/mol
CAS Registry NumberNot Available
IUPAC Name(2R)-2-[(3Z,7E,11Z)-13-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Name(2R)-2-[(3Z,7E,11Z)-13-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-6-ol
SMILESC\C(CO)=C\CC\C(C)=C\CC\C(C)=C/CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C
InChI IdentifierInChI=1S/C29H44O3/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/h11,14-15,30-31H,8-10,12-13,16-19H2,1-7H3/b20-11+,21-15-,22-14-/t29-/m1/s1
InChI KeyOQCXIVSCFNNFEE-QFLITSPGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocopherols that contain a saturated trimethyltridecyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentTocotrienols
Alternative Parents
Substituents
  • Tocotrienol
  • 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 DescriptorsNot Available
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 Solubility0.00043 g/LALOGPS
logP6.85ALOGPS
logP8.01ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)10.8ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity139.7 m³·mol⁻¹ChemAxon
Polarizability55.01 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1494700000-f173734009313705349bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01di-0254590000-f80dee238accdcff5fa0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r6-0522900000-f0a973aa229cc0e18057Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0910100000-01cd3475e51c622ef641Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1910000000-bf2f39b416dc83d44afdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-66e57cd8765e9e02ba8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ri-0410900000-fb038a84c9fe65219c3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01pk-0924200000-80df0759bcd6643cf99fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0000900000-299ff46aecbcb35eef14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0513900000-ba8bc35ffb27ad020a18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbl-1359100000-dd581c07c01dc0d00e6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-1249600000-bd452cc5c74a0595b8c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07vj-2398100000-357220cc09bf37811f38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-7950000000-d161605aef70e137c675Spectrum
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 IDHMDB0012560
FooDB IDFDB029126
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776634
ChEBI ID145208
PubChem Compound ID53481466
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. The lipid handbook with CD-ROM