11'-Carboxy-alpha-tocotrienol (CHEM040932)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:05:07 UTC
Update Date2016-11-09 01:22:21 UTC
Accession NumberCHEM040932
Identification
Common Name11'-Carboxy-alpha-tocotrienol
ClassSmall Molecule
Description11'-Carboxy-alpha-tocotrienol is a dehydrogenation carboxylate product of 11'-hydroxy-a-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
11'-Carboxy-a-tocotrienolGenerator
11'-Carboxy-α-tocotrienolGenerator
alpha-CDMD(En)(,2)HCHMDB
alpha-CDMD(En)(2)HCHMDB
(4E,8E)-11-[(2R)-6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundeca-4,8-dienoateGenerator
Chemical FormulaC26H38O4
Average Molecular Mass414.578 g/mol
Monoisotopic Mass414.277 g/mol
CAS Registry NumberNot Available
IUPAC Name(4E,8E)-11-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundeca-4,8-dienoic acid
Traditional Name(4E,8E)-11-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-4,8-dimethylundeca-4,8-dienoic acid
SMILESC\C(CC\C=C(/C)CCC(O)=O)=C/CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C
InChI IdentifierInChI=1S/C26H38O4/c1-17(9-7-10-18(2)12-13-23(27)28)11-8-15-26(6)16-14-22-21(5)24(29)19(3)20(4)25(22)30-26/h10-11,29H,7-9,12-16H2,1-6H3,(H,27,28)/b17-11+,18-10+/t26-/m1/s1
InChI KeyLAVCYAUSHCEKED-KYVGBUAPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Long-chain fatty acid
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Alkyl aryl ether
  • Branched fatty acid
  • Heterocyclic fatty acid
  • Methyl-branched fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Unsaturated fatty acid
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • 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 Solubility0.0007 g/LALOGPS
logP5.53ALOGPS
logP7.2ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.93ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity124.99 m³·mol⁻¹ChemAxon
Polarizability50.38 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, Positivesplash10-052g-3598000000-0794d2e3b97f862e8655Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-002f-3375590000-ea3e3b7bc622a99d4c9cSpectrum
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, Positivesplash10-014j-0529200000-30b89875176e2b7a0c42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0911000000-9af27c54347c9a05670cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1910000000-d5dc9676ca1c0a060329Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0003900000-9333874001868a24d0b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2629500000-c66d5953b0fef0659bb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pc1-5923000000-3d68306545b7d153d809Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-0009600000-35c8b614fd6a280cdcc5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07vl-9307200000-d1691133fbf6cb8c3c12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-1003-1193000000-f5505943c7c01754cde5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02t9-0059100000-a53b4fbb38b1b24705e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07vm-1093000000-cc287b7f9e317165d043Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4691000000-df7d63d38a0d4bb4c8aaSpectrum
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 IDHMDB0012516
FooDB IDFDB029109
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776618
ChEBI ID175317
PubChem Compound ID53481452
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