Livestock Metabolome Database: Showing metabocard for Alpha-Tocopherol (LMDB00364)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:48:11 UTC

Update Date

2018-04-30 21:14:45 UTC

Lmdb

LMDB00364

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Alpha-Tocopherol

Description

Alpha-tocopherol is traditionally recognized as the most active form of vitamin E in animals, and is a powerful biological antioxidant. The measurement of "vitamin E" activity in international units (IU) was based on fertility enhancement by the prevention of spontaneous abortions in pregnant rats relative to alpha tocopherol. Natural vitamin E exists in eight different forms or isomers, four tocopherols and four tocotrienols. In foods, the most abundant sources of vitamin E are vegetable oils such as palm oil, sunflower, corn, soybean and olive oil. Nuts, sunflower seeds, and wheat germ are also good sources. --Wikipedia.

Structure

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

Synonyms

Value	Source
(2R,4'R,8'R)-alpha-Tocopherol	ChEBI
(R,R,R)-alpha-Tocopherol	ChEBI
5,7,8-Trimethyltocol	ChEBI
d-alpha-Tocopherol	ChEBI
Vitamin e	ChEBI
(2R,4'r,8'r)-a-Tocopherol	Generator
(2R,4'R,8'R)-α-Tocopherol	Generator
a-Tocopherol	Generator
α-Tocopherol	Generator
(R,R,R)-a-Tocopherol	Generator
(R,R,R)-α-Tocopherol	Generator
D-a-Tocopherol	Generator
d-α-Tocopherol	Generator
(+)-a-Tocopherol	HMDB
(+)-alpha-Tocopherol	HMDB
(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-Tocopherol	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
(+)-α-Tocopherol	HMDB
(2R,4’R,8’R)-α-Tocopherol	HMDB
(all-R)-alpha-Tocopherol	HMDB
(all-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 but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-000i-1390000000-fc8c4f9b9405598ede7f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-00dr-9150010000-c4abc0e689e9b2476b9d	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0f79-1190040000-663296a69129a59be1a6	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-1390000000-fc8c4f9b9405598ede7f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-9150010000-c4abc0e689e9b2476b9d	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0f79-1190040000-663296a69129a59be1a6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aor-9886300000-b3225facac6ebdd8ddbd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-000l-7735900000-1585eb83c1211ebe95f2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-9600100000-aaf885290800a10d3fb2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-01wr-9300000000-f0c814976a58a9d837ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0f79-1494700000-6b5f8f817c5a5429ed70	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positive	splash10-00lr-4910600000-1eda05dacf9642d7cea0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-a5860634bfd1ceb6833f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0159-0900500000-5a3bc17152cb61859b2c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0842900000-f51286676592fd184193	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-1920000000-1994f86bec2bb4a77b9c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066r-3930000000-02190bf16d5d85d44bce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0110900000-c3541294fc60a7a8cc7e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-0730900000-553c4898757f6876036c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03e9-0920200000-276273a531fed5b3a2b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-3013900000-4985082235edff7c4b8c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05r1-9313200000-cbc230d5dd20c629ffab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9320000000-5958d2e1d5b687b012c1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-d3ddef81c134412455e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0310900000-30597e14cf876e4e4764	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-08g0-2982400000-371737325df4dbb523b2	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0159-2900500000-03e8a824731610752eb3	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk
Muscle
Plasma
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Muscle	Detected but not Quantified	Not Applicable	Not Available	Bovine	23871026	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24070026	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details