Milk Composition Database: Showing metabocard for Gamma-Tocopherol (BMDB0001492)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:46:43 UTC

Update Date

2020-06-04 19:14:00 UTC

MCDB ID

BMDB0001492

Secondary Accession Numbers

BMDB01492

Metabolite Identification

Common Name

Gamma-Tocopherol

Description

Gamma-Tocopherol, also known as vitaplus e or DL-alpha-tocopherol, 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. Gamma-Tocopherol exists as a liquid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
DL-alpha-Tocopherol	Kegg
DL-a-Tocopherol	Generator
DL-Α-tocopherol	Generator
g-Tocopherol	Generator
Γ-tocopherol	Generator
3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol	HMDB
7,8-Dimethyltocol	HMDB
7,8-Dimethyltocolo-xylotocopherol	HMDB
Methyltocols	HMDB
O-Xylotocopherol	HMDB
Tocopherol	HMDB
Tocopherols	HMDB
Vitamin e gamma	HMDB
Bioweyxin	HMDB
e-Mulsin	HMDB
Embial	HMDB
GNR-Pharma brand OF tocopherol actetate	HMDB
Organon brand OF tocopherol acetate	HMDB
Schwarzhaupt brand OF tocopherol acetate	HMDB
Snow-e muscle, energy and feritility	HMDB
Spondyvit	HMDB
Tocolion	HMDB
Tocopherol rodisma-med brand	HMDB
Tocopherol worwag brand	HMDB
Togasan vitamin e	HMDB
Unique e	HMDB
Vibolex	HMDB
Vita-e	HMDB
Vitamin e dragees	HMDB
Atarost brand OF tocopherol acetate	HMDB
Biocur brand OF tocopherol acetate	HMDB
Cambridge laboratories brand OF tocopherol actetate	HMDB
Dal e	HMDB
Detulin	HMDB
e Vitamin e	HMDB
EVI-mirale, vitamin-e	HMDB
Elex verla	HMDB
Eplonat	HMDB
Richelet brand OF tocopherol acetate	HMDB
Roche nicholas brand OF tocopherol acetate	HMDB
Rodisma med brand OF tocopherol	HMDB
Sciencex brand OF tocopherol acetate	HMDB
Steigerwald brand OF tocopherol acetate	HMDB
Strathmann brand OF tocopherol	HMDB
Tocopherol grunwalder brand	HMDB
Tocopherol stadapharm brand	HMDB
Verla brand OF tocopherol	HMDB
Vit. e stada	HMDB
VitaPlus e	HMDB
Vitamin-e evi-mirale	HMDB
Vitamine e GNR	HMDB
Vitazell	HMDB
Worwag brand OF tocopherol	HMDB
Alcala brand OF tocopherol acetate	HMDB
Bio e	HMDB
Biopto-e	HMDB
e Vicotrat	HMDB
e-Ferol	HMDB
EUNOVA vitamin e	HMDB
Equivit e	HMDB
Evion	HMDB
Internation animal health brand OF tocopherol acetate	HMDB
MIP brand OF tocopherol acetate	HMDB
Sanum-kehlbeck brand OF tocopherol actetate	HMDB
Tocopherol infirmarius-rovit brand	HMDB
Tocopherol twardy brand	HMDB
Tocovital	HMDB
Vitamin-e dragees	HMDB
Wiedemann brand OF tocopherol	HMDB
Abortosan	HMDB
Arkopharma brand OF tocopherol acetate	HMDB
Dal vita brand OF vitamin e succinate	HMDB
Eu rho brand OF tocopherol	HMDB
Eusovit	HMDB
Infirmarius-rovit brand OF tocopherol	HMDB
Richtavit e	HMDB
Riemser brand OF tocopherol	HMDB
Tocopherol ausrichter brand	HMDB
Tocopherol balkanpharma brand	HMDB
Vitagutt vitamin e	HMDB
Vitamin e natur	HMDB
Vitamin e, togasan	HMDB
Ratiopharm brand OF tocopherol	HMDB
Aliud brand OF tocopherol	HMDB
Bottger brand OF tocopherol acetate	HMDB
Dermorelle	HMDB
e Ferol	HMDB
e-Vitamin-ratiopharm	HMDB
Heyl brand OF tocopherol acetate	HMDB
Kohler brand OF tocopherol	HMDB
Lasar	HMDB
Puncto e	HMDB
Rodisma-med brand OF tocopherol	HMDB
Sanum kehlbeck brand OF tocopherol actetate	HMDB
Scot tussin brand OF tocopherol acetate	HMDB
Stadapharm brand OF tocopherol	HMDB
Tocopa	HMDB
Tocopherol bayer	HMDB
Tocopherol grace brand	HMDB
Tocopherol ratiopharm brand	HMDB
Twardy brand OF tocopherol	HMDB
Uno vit	HMDB
Uno-vit	HMDB
Veyx brand OF tocopherol	HMDB
Vit e hydrosol	HMDB
Vita e	HMDB
Vitamin e al	HMDB
Wiedemann brand OF vitamin e succinate	HMDB
Ausrichter brand OF tocopherol	HMDB
Auxina e	HMDB
Balkanpharma brand OF tocopherol	HMDB
Blackmores brand OF tocopherol	HMDB
Dal-e	HMDB
Davitamon	HMDB
e-Vicotrat	HMDB
Ecoro	HMDB
Ephynal	HMDB
Grunwalder brand OF tocopherol	HMDB
ICN brand OF tocopherol acetate	HMDB
Mucos brand OF tocopherol acetate	HMDB
Tocopherol togal brand	HMDB
Tocopherol verla brand	HMDB
Togal brand OF tocopherol	HMDB
Troyapharm brand OF tocopherol acetate	HMDB
Vita-plus e	HMDB
Vitamin e sanum	HMDB
Vitamin e MP	HMDB
Vitamin emp	HMDB
Woelm brand OF tocopherol acetate	HMDB
Bayer brand OF tocopherol acetate	HMDB
GNR Pharma brand OF tocopherol actetate	HMDB
Grace brand OF tocopherol	HMDB
Malton e	HMDB
Merck brand OF tocopherol acetate	HMDB
Mowivit vitamin e	HMDB
Tocopherol wiedemann brand	HMDB
UnoVit	HMDB
Vitamin e evi mirale	HMDB
Vitamin e suspension	HMDB
Vitamin e, mowivit	HMDB
Vitamin e, vitagutt	HMDB
Vitamin e-MP	HMDB
Adisseo brand OF tocopherol	HMDB
Antioxidans e-hevert	HMDB
Aquasol e	HMDB
AstraZeneca brand OF tocopherol acetate	HMDB
Biosan	HMDB
Dal-vita brand OF vitamin e succinate	HMDB
Dragees, vitamin-e	HMDB
e Mulsin	HMDB
Hervert brand OF tocopherol acetate	HMDB
Hydrovit e	HMDB
Infirmarius rovit brand OF tocopherol	HMDB
Jenapharm brand OF tocopherol	HMDB
Kentucky brand OF tocopherol	HMDB
Micorvit e	HMDB
Sanavitan S	HMDB
Scot-tussin brand OF tocopherol acetate	HMDB
Tocopharm	HMDB
Tocopherol kentucky brand	HMDB
Vita plus e	HMDB
VitaE	HMDB
Medphano brand OF tocopherol acetate	HMDB
VitaminE evimirale	HMDB

Chemical Formula

C₂₈H₄₈O₂

Average Molecular Weight

416.6795

Monoisotopic Molecular Weight

416.36543078

IUPAC Name

2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-1-benzopyran-6-ol

CAS Registry Number

1406-66-2

SMILES

CC(C)CCCC(C)CCCC(C)CCCC1(C)CCC2=CC(O)=C(C)C(C)=C2O1

InChI Identifier

InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3

InChI Key

QUEDXNHFTDJVIY-UHFFFAOYSA-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
1-hydroxy-2-unsubstituted benzenoid
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

vitamin E (GAMA-TOCOPHEROL )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	128 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	8.81	ALOGPS
logP	9.99	ChemAxon
logS	-7.8	ALOGPS
pKa (Strongest Acidic)	10.47	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	130.33 m³·mol⁻¹	ChemAxon
Polarizability	54.13 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0lyo-7964200000-f0d5087bb29d80c38248	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-5644900000-85c7bfa3df1a86febfeb	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-1842900000-c0a3ade1f225f3c78ac2	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-1910000000-db436d443f9dc640b979	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pb9-5930000000-1cbe4445929c9b90be47	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0110900000-23d01b80a965180b27d9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-0931800000-70e6ff42d0190b91ef52	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0932000000-e16b76b24d1cd56f30b1	2016-08-03	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.0264 +/- 0.0072 uM	International Dai...	details
Detected and Quantified	0.1 +/- 0.01 uM	International Dai...	details
Detected but not Quantified	Not Applicable	PMID: 11913692	details

External Links

HMDB ID

HMDB0001492

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002431

KNApSAcK ID

C00007365

Chemspider ID

14266

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

298402

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]
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.

Showing metabocard for Gamma-Tocopherol (BMDB0001492)

Structure for BMDB0001492 (Gamma-Tocopherol)