AFCDB: alpha-Tocopherol (FDB000565)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:37 UTC

Update date

2019-11-26 02:55:00 UTC

Primary ID

FDB000565

Secondary Accession Numbers

FDB005752

Chemical Information

FooDB Name

alpha-Tocopherol

Description

Constituent of many vegetable oils such as soya and sunflower oils. Dietary supplement and nutrient. Nutriceutical with anticancer and antioxidant props. Added to fats and oils to prevent rancidity. The naturally-occurring tocopherol is a single stereoisomer; synthetic forms are a mixture of all eight possible isomers Alpha-tocopherol is traditionally recognized as the most active form of vitamin E in humans, and is a powerful biological antioxidant. alpha-Tocopherol is found in many foods, some of which are custard apple, nopal, bitter gourd, and kumquat.

CAS Number

59-02-9

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	7.0e-06 g/L	ALOGPS
logP	8.84	ALOGPS
logP	10.51	ChemAxon
logS	-7.8	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	12	ChemAxon
Refractivity	135.37 m³·mol⁻¹	ChemAxon
Polarizability	55.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C29H50O2

IUPAC name

(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol

InChI Identifier

InChI=1S/C29H50O2/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/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1

InChI Key

GVJHHUAWPYXKBD-IEOSBIPESA-N

Isomeric SMILES

CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C

Average Molecular Weight

430.7061

Monoisotopic Molecular Weight

430.381080844

Classification

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Tocopherols

Alternative Parents

Substituents

Tocopherol
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

alpha-tocopherol (CHEBI:18145 )
vitamin E (C02477 )
Fat-soluble vitamins (C02477 )
Vitamin E (LMPR02020000 )

Ontology

Thyroid cancer

Food

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Hormone

Modulator:

Immunomodulator

Industrial application:

Food and nutrition:

Nutritional supplement

Pharmaceutical industry:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 80.87%; H 11.70%; O 7.43%	DFC
Melting Point	Mp 2.5-3.5°	DFC
Boiling Point	Bp0.03 140°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]25D +0.65 (EtOH)	DFC
Spectroscopic UV Data	[neutral] lmax 292 () (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0159-2900500000-03e8a824731610752eb3	2014-09-20	View Spectrum
GC-MS	alpha-Tocopherol, 1 TMS, GC-MS Spectrum	splash10-000i-1390000000-fc8c4f9b9405598ede7f	Spectrum
GC-MS	alpha-Tocopherol, 1 TMS, GC-MS Spectrum	splash10-00dr-9150010000-c4abc0e689e9b2476b9d	Spectrum
GC-MS	alpha-Tocopherol, 1 TMS, GC-MS Spectrum	splash10-0f79-1190040000-663296a69129a59be1a6	Spectrum
GC-MS	alpha-Tocopherol, non-derivatized, GC-MS Spectrum	splash10-000i-1390000000-fc8c4f9b9405598ede7f	Spectrum
GC-MS	alpha-Tocopherol, non-derivatized, GC-MS Spectrum	splash10-00dr-9150010000-c4abc0e689e9b2476b9d	Spectrum
GC-MS	alpha-Tocopherol, non-derivatized, GC-MS Spectrum	splash10-0f79-1190040000-663296a69129a59be1a6	Spectrum
Predicted GC-MS	alpha-Tocopherol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0aor-9886300000-b3225facac6ebdd8ddbd	Spectrum
Predicted GC-MS	alpha-Tocopherol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000l-7735900000-1585eb83c1211ebe95f2	Spectrum
Predicted GC-MS	alpha-Tocopherol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	alpha-Tocopherol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-9600100000-aaf885290800a10d3fb2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-01wr-9300000000-f0c814976a58a9d837ca	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0f79-1494700000-6b5f8f817c5a5429ed70	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positive	splash10-00lr-4910600000-1eda05dacf9642d7cea0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-a5860634bfd1ceb6833f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0159-0900500000-5a3bc17152cb61859b2c	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0842900000-f51286676592fd184193	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-1920000000-1994f86bec2bb4a77b9c	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066r-3930000000-02190bf16d5d85d44bce	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0110900000-c3541294fc60a7a8cc7e	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-0730900000-553c4898757f6876036c	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03e9-0920200000-276273a531fed5b3a2b0	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-3013900000-4985082235edff7c4b8c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05r1-9313200000-cbc230d5dd20c629ffab	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9320000000-5958d2e1d5b687b012c1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-d3ddef81c134412455e1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0310900000-30597e14cf876e4e4764	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-08g0-2982400000-371737325df4dbb523b2	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB00163

HMDB ID

HMDB01893

CRC / DFC (Dictionary of Food Compounds) ID

BDR14-R:BDR14-R

EAFUS ID

Not Available

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Alpha-Tocopherol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti Alzheimeran	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti anginal	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti arthritic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti asthmatic	49167	A drug used to treat asthma.	DUKE
anti atherosclerotic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti cataract	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti convulsant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti dementia	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti diabetic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti infarctal	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti infertility	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti ischemic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti maculitic			DUKE
anti mutagenic			DUKE
anti neuropathic			DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti Parkinsonian	48407	A drug used in the treatment of Parkinson's disease.	DUKE
anti radicular			DUKE
anti retinotic			DUKE
anti rheumatic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti stroke	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
antitumor promoter	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cardioprotective	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
circulotonic			DUKE
immunomodulator	50846	Biologically active substance whose activity affects or plays a role in the functioning of the immune system.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Nuclear receptor subfamily 1 group I member 2	NR1I2	O75469
Glutamate--cysteine ligase catalytic subunit	GCLC	P48506
Glutathione S-transferase Mu 3	GSTM3	P21266
Glutathione S-transferase omega-1	GSTO1	P78417
Glutathione S-transferase A2	GSTA2	P09210
Glutathione S-transferase P	GSTP1	P09211
Serine palmitoyltransferase 1	SPTLC1	O15269
Alpha-tocopherol transfer protein	TTPA	P49638

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

alpha-Tocopherol (FDB000565)

Structure for FDB000565 (alpha-Tocopherol)