Bovine Metabolome Database: Showing metabocard for Alpha-Tocopherol (BMDB0001893)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:48:43 UTC

Update Date

2020-06-04 20:46:14 UTC

BMDB ID

BMDB0001893

Secondary Accession Numbers

BMDB01893

Metabolite Identification

Common Name

Alpha-Tocopherol

Description

Alpha-Tocopherol, also known as D-α-tocopherol or vitamin e, 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. Thus, Alpha-tocopherol is considered to be a quinone lipid molecule. Alpha-Tocopherol exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Alpha-Tocopherol exists in all living organisms, ranging from bacteria to humans. Alpha-Tocopherol is a potentially toxic compound. Alpha-Tocopherol has been found to be associated with several diseases known as parkinson's disease, thyroid cancer, cerebrotendinous xanthomatosis, and vitamin e deficiency; also alpha-tocopherol has been linked to the inborn metabolic disorders including abetalipoproteinemia.

Structure

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

Synonyms

Value	Source
(+)-alpha-Tocopherol	ChEBI
(2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol	ChEBI
(2R,4'r,8'r)-alpha-Tocopherol	ChEBI
(all-R)-alpha-Tocopherol	ChEBI
5,7,8-Trimethyltocol	ChEBI
D-alpha-Tocopherol	ChEBI
RRR-alpha-Tocopherol	ChEBI
Vitamin e	ChEBI
(+)-a-Tocopherol	Generator
(+)-Α-tocopherol	Generator
(2R,4'r,8'r)-a-Tocopherol	Generator
(2R,4'r,8'r)-Α-tocopherol	Generator
(all-R)-a-Tocopherol	Generator
(all-R)-Α-tocopherol	Generator
D-a-Tocopherol	Generator
D-Α-tocopherol	Generator
RRR-a-Tocopherol	Generator
RRR-Α-tocopherol	Generator
a-Tocopherol	Generator
Α-tocopherol	Generator
(R,R,R)-alpha-Tocopherol	ChEBI
(R,R,R)-a-Tocopherol	Generator
(R,R,R)-α-Tocopherol	Generator
(2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol	HMDB
a-D-Tocopherol	HMDB
alpha-delta-Tocopherol	HMDB
delta-alpha-Tocopherol	HMDB
Denamone	HMDB
Eprolin	HMDB
Phytogermin	HMDB
Phytogermine	HMDB
RRR-alpha-Tocopheryl	HMDB
Vitamin ea	HMDB
alpha-Tocopherol	ChEBI
(+)-2R,4'R,8'R-alpha-Tocopherol	HMDB
(+)-2R,4'R,8'R-α-Tocopherol	HMDB
(+)-2R,4’R,8’R-α-Tocopherol	HMDB
(2R,4’R,8’R)-α-Tocopherol	HMDB
3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-(2R)-2H-1-benzopyran-6-ol	HMDB
alpha-D-Tocopherol	HMDB
alpha-Vitamin E	HMDB
α-D-Tocopherol	HMDB
α-Vitamin E	HMDB
Almefrol	PhytoBank
Emipherol	PhytoBank
Etamican	PhytoBank
Evitaminum	PhytoBank
Profecundin	PhytoBank
Vitamin Ealpha	PhytoBank
Vitamin Eα	PhytoBank

Chemical Formula

C₂₉H₅₀O₂

Average Molecular Weight

430.7061

Monoisotopic Molecular Weight

430.381080844

IUPAC Name

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

Traditional Name

VitaE

CAS Registry Number

59-02-9

SMILES

CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1

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

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.

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

Status

Detected and Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Adipose Tissue
Bladder
Blood
Epidermis
Erythrocyte
Eye Lens
Fibroblasts
Intestine
Leukocyte
Liver
Milk
Muscle
Neuron
Pancreas
Placenta
Platelet
Prostate Tissue
Skeletal Muscle
Spleen
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Bladder	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Erythrocyte	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Eye Lens	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Leukocyte	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 11913692	details
Milk	Detected and Quantified	1.161 - 7.685 uM	Not Specified	Not Specified	Normal	PMID: 1333471	details
Milk	Detected and Quantified	1.509 uM	Not Specified	Not Specified	Normal	PMID: 16772583	details
Milk	Detected and Quantified	1.37 - 1.69 uM	Not Specified	Not Specified	Normal	Chotyakul N, Pate...	details
Milk	Detected and Quantified	0.16 - 0.21 uM	Not Specified	Not Specified	Normal	Chotyakul N, Pate...	details
Milk	Detected and Quantified	3.0183 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.232 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.232 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	1.857 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.232 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.232 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.232 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.232 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.929 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.697 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.697 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.871 +/- 0.0279 uM	Not Specified	Not Specified	Normal	International Dai...	details
Milk	Detected and Quantified	1.983 +/- 0.0720 uM	Not Specified	Not Specified	Normal	International Dai...	details
Milk	Detected and Quantified	1.625 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	1.625 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	1.120 +/- 0.100 uM	Not Specified	Not Specified	Normal	International Dai...	details
Milk	Detected and Quantified	2.0800 +/- 0.830 uM	Not Specified	Not Specified	Normal	International Dai...	details
Milk	Detected and Quantified	0.950 +/- 0.490 uM	Not Specified	Not Specified	Normal	International Dai...	details
Milk	Detected and Quantified	0.697 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	0.929 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	0.232 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	0.302 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	0.232 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	2.0896 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	1.393 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	1.974 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	1.90 - 2.16 uM	Not Specified	Not Specified	Normal	Chotyakul N, Pate...	details
Milk	Detected and Quantified	0.464 - 2.322 uM	Not Specified	Not Specified	Normal	Graulet B: Improv...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Milk	Detected and Quantified	0.464 - 4.179 uM	Not Specified	Not Specified	Normal	Oste R, Jagerstad...	details
Milk	Detected and Quantified	0.5 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.8 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.9 +/- 0.2 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.5 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23871026	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Pancreas	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Spleen	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Sub/clinical ketosis	PMID: 24070026	details

External Links

HMDB ID

HMDB0001893

DrugBank ID

DB00163

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

18145

References

Synthesis Reference

Matsui, Makoto. Synthesis of a-tocopherol for the next century. Nihon Yukagakkaishi (1996), 45(9), 821-831.

Material Safety Data Sheet (MSDS)

Not Available

General References

Delgado Zamarreno MM, Sanchez Perez A, Gomez Perez C, Hernandez Mendez J: High-performance liquid chromatography with electrochemical detection for the simultaneous determination of vitamin A, D3 and E in milk. J Chromatogr. 1992 Oct 9;623(1):69-74. [PubMed:1333471 ]
Noziere P, Grolier P, Durand D, Ferlay A, Pradel P, Martin B: Variations in carotenoids, fat-soluble micronutrients, and color in cows' plasma and milk following changes in forage and feeding level. J Dairy Sci. 2006 Jul;89(7):2634-48. doi: 10.3168/jds.S0022-0302(06)72340-2. [PubMed:16772583 ]
Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
M.S Havemose, Martin Riis Weisbjerg, Wender L.P Bredie, J.H Nielsen (2004). International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570. International Dairy Journal.
M.C. Herrero-Barbudo, F. Granado-Lorencio, I. Blanco-Navarro, B. Olmedilla-Alonso (2005). International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526. International Dairy Journal.
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
Nattaporn Chotyakul, Miriam Pateiro-Moure, Jorge Alexandre Saraiva, J. Antonio Torres, Concepción Pérez-Lamela (2014). Chotyakul N, Pateiro-Moure M, Saraiva JA, Torres JA, Pérez-Lamela C. 2014. Simultaneous HPLC–DAD quantification of vitamins A and E content in raw, pasteurized, and UHT cow’s milk and their changes during storage. European Food Research and Technology. 238(4):535–547 . European Food Research and Technology.
Graulet B (2010). Graulet B: Improving the level of vitamins in milk. In Griffiths MW (ed):‘‘Improving the Safety and Quality of Milk: Improving Quality in Milk Products,’’vol. 2. Boca Raton, FL: CRC Press, pp 229–251, 2010.. CRC Press.
Oste R, Jagerstad M, Anderson I (1997). Oste R, Jagerstad M, Anderson I: Vitamins in milk and milk products. In Fox PF (ed):‘‘Advanced Dairy Chemistry: Lactose, Water, Salts and Vitamins,’’vol 3, 2nd ed. London: Chapman & Hall, pp 347–402, 1997. Chapman & Hall.
USDA Food Composition Databases [Link]
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for Alpha-Tocopherol (BMDB0001893)

Structure for BMDB0001893 (Alpha-Tocopherol)