Showing Compound (R)-alpha-Tocotrienol (FDB002434)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:22 UTC

Update date

2019-11-26 02:57:27 UTC

Primary ID

FDB002434

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(R)-alpha-Tocotrienol

Description

(R)-alpha-Tocotrienol, also known as (R)-α-tocotrienol, 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 (R)-alpha-Tocotrienol is an extremely weak basic (essentially neutral) compound (based on its pKa).

CAS Number

1721-51-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2R,3'E,7'E)-alpha-Tocotrienol	biospider
(R)-a-Tocotrienol	Generator
(r)-alpha-tocotrienol	biospider
(R)-Α-tocotrienol	Generator
a-Tocotrienol	Generator
Alpha-tocotrienol	biospider
D-alpha-tocotrienol	biospider
Delta-alpha-tocotrienol	biospider
Tocotrienol, alpha	biospider
Z1-Tocopherol	Generator

Showing 1 to 10 of 13 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.00027 g/L	ALOGPS
logP	7.7	ALOGPS
logP	9.29	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	10.8	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	137.92 m³·mol⁻¹	ChemAxon
Polarizability	53.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C29H44O2

IUPAC name

2,5,7,8-tetramethyl-2-[(3Z,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol

InChI Identifier

InChI=1S/C29H44O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h12,14,16,30H,9-11,13,15,17-19H2,1-8H3/b21-14+,22-16-

InChI Key

RZFHLOLGZPDCHJ-AOOUSOOLSA-N

Isomeric SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C/CCC1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C

Average Molecular Weight

424.6585

Monoisotopic Molecular Weight

424.334130652

Classification

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Tocotrienols

Alternative Parents

Substituents

Tocotrienol
Diterpenoid
1-benzopyran
Benzopyran
Chromane
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 82.02%; H 10.44%; O 7.54%	DFC
Melting Point	Mp 30-31°	DFC
Optical Rotation	[a]25D -5.7 (c, 1.01 in CHCl3)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0943700000-e7e4f29a49bdd3dc809a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0910000000-185145ea1654aa2dca7e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-2910000000-a15053dafac85cbc3b41	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0110900000-0e442666a65bbf22ac09	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0229-0831900000-3811650fc0f5bea6c649	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06sj-0920200000-14794f8dbb7623030f58	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

33270

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB06327

CRC / DFC (Dictionary of Food Compounds) ID

CLT28-X:CLT29-Y

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

2296493

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Annual wild rice	Expected but not quantified	Not Available	MANUAL
Barley	Expected but not quantified	Not Available	MANUAL
Bulgur	Expected but not quantified	Not Available	MANUAL
Common buckwheat	Expected but not quantified	Not Available	MANUAL
Common wheat	Expected but not quantified	Not Available	MANUAL
Corn	Expected but not quantified	Not Available	MANUAL
Flour	Expected but not quantified	Not Available	MANUAL
Hard wheat	Expected but not quantified	Not Available	MANUAL
Millet	Expected but not quantified	Not Available	MANUAL
Oat	2.210 - 2.210	2.210	MANUAL, USDA