ChemFOnt: Showing chemical card for Vitamin E (CFc000334011)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:14:41 UTC

Chemfont ID

CFc000334011

Molecule Identification

Common Name

Vitamin E

Definition

Alpha-tocopherol, also known as (2r,4'r,8'r)-alpha-tocopherol or vitamin e, is a member of the class of compounds known as tocopherols. Tocopherols 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 is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Alpha-tocopherol can be found in a number of food items such as green zucchini, capers, saskatoon berry, and coconut, which makes alpha-tocopherol a potential biomarker for the consumption of these food products. Alpha-tocopherol can be found primarily in most biofluids, including saliva, blood, cerebrospinal fluid (CSF), and feces, as well as throughout most human tissues. Moreover, alpha-tocopherol is found to be associated with thyroid cancer and parkinson's disease. Alpha-tocopherol is a non-carcinogenic (not listed by IARC) potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

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 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0001893)

Food

Soy

Soy bean (FooDB: FOOD00085)

Vegetable

Cabbage

Broccoli (FooDB: FOOD00034)

Leaf vegetable

Lettuce (FooDB: FOOD00095)

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Fruit vegetable

Green bell pepper (FooDB: FOOD00877)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Orange bell pepper (FooDB: FOOD00879)

Fruit

Tropical fruit

Coconut (FooDB: FOOD00336)

Berry

Sea-buckthornberry (FooDB: FOOD00087)
Saskatoon berry (FooDB: FOOD00884)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Herb and spice

Spice

Capers (FooDB: FOOD00039)

Cereal and cereal product

Cereal

Common wheat (FooDB: FOOD00187)

Gourd

Green zucchini (FooDB: FOOD00875)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)

Pulse

Bean

Green bean (FooDB: FOOD00883)

Process

Not Available

Role

Industrial applicationBiological role

Modulator

Inhibitor

Enzyme inhibitor

Lipoxygenase inhibitor (HMDB: HMDB0001893)
Ornithine-decarboxylase inhibitor (HMDB: HMDB0001893)

EC 3.1.1.4 (phospholipase A2) inhibitor (HMDB: HMDB0001893)
EC 2.7.11.13 (protein kinase C) inhibitor (HMDB: HMDB0001893)

5-hydroxyeicosatetraenoic-acid inhibitor (HMDB: HMDB0001893)
Apoptotic (HMDB: HMDB0001893)

Allergen (HMDB: HMDB0001893)
Anti aggregant (HMDB: HMDB0001893)
Anti aging (HMDB: HMDB0001893)
Anti Alzheimeran (HMDB: HMDB0001893)
Anti anginal (HMDB: HMDB0001893)
Anti arteriosclerotic (HMDB: HMDB0001893)
Anti atherosclerotic (HMDB: HMDB0001893)
Anti bronchitic (HMDB: HMDB0001893)
Anti cariogenic (HMDB: HMDB0001893)
Anti cataract (HMDB: HMDB0001893)
Anti chorea (HMDB: HMDB0001893)
Anti coronary (HMDB: HMDB0001893)
Anti decubitic (HMDB: HMDB0001893)
Anti dermatitic (HMDB: HMDB0001893)
Anti diabetic (HMDB: HMDB0001893)
Anti dysmenorrheic (HMDB: HMDB0001893)
Anti epitheleomic (HMDB: HMDB0001893)
Anti fibrositic (HMDB: HMDB0001893)
Anti herpetic (HMDB: HMDB0001893)
Anti-inflammatory (HMDB: HMDB0001893)
Anti ischaemic (HMDB: HMDB0001893)
Anti leukemic (HMDB: HMDB0001893)
Anti leukotriene (HMDB: HMDB0001893)
Anti lithic (HMDB: HMDB0001893)
Anti lupus (HMDB: HMDB0001893)
Anti mastalgic (HMDB: HMDB0001893)
Anti MD (HMDB: HMDB0001893)
Anti monosodium-glutamate (HMDB: HMDB0001893)
Anti myoclonic (HMDB: HMDB0001893)
Anti neuritic (HMDB: HMDB0001893)
Anti nitrosaminic (HMDB: HMDB0001893)
Anti ophthalmic (HMDB: HMDB0001893)
Anti osteoarthritic (HMDB: HMDB0001893)
Anti Parkinsonian (HMDB: HMDB0001893)
Anti premenstrual syndrome (HMDB: HMDB0001893)
Anti proliferant (HMDB: HMDB0001893)
Anti radicular (HMDB: HMDB0001893)
Anti retinopathic (HMDB: HMDB0001893)
Anti senility (HMDB: HMDB0001893)
Anti sickling (HMDB: HMDB0001893)
Anti spasmodic (HMDB: HMDB0001893)
Anti sterility (HMDB: HMDB0001893)
Anti stroke (HMDB: HMDB0001893)
Anti sunburn (HMDB: HMDB0001893)
Anti syndrome-X (HMDB: HMDB0001893)
Anti thalassemic (HMDB: HMDB0001893)
Anti thrombotic (HMDB: HMDB0001893)
Anti thromboxane-B2 (HMDB: HMDB0001893)
Anti toxemic (HMDB: HMDB0001893)
Anti ulcerogenic (HMDB: HMDB0001893)
Cerebroprotective (HMDB: HMDB0001893)
Circulatory stimulant (HMDB: HMDB0001893)
Hypocholesterolemic (HMDB: HMDB0001893)
Insulin-sparing (HMDB: HMDB0001893)
Cytochrome-P21 inducer (HMDB: HMDB0001893)

Physical Properties

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