ChemFOnt: Showing chemical card for 13'-Hydroxy-alpha-tocopherol (CFc000008035)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:39 UTC

Chemfont ID

CFc000008035

Molecule Identification

Common Name

13'-Hydroxy-alpha-tocopherol

Definition

13'-hydroxy-alpha-tocopherol is the precursor in dehydrogenation to 13'-carboxy-alpha-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. The tocopherols ( a-tocopherol , b-tocopherol ,r-tocopherol and d-tocopherol ) and their corresponding tocotrienols are synthesized by plants and have vitamin E antixoidant activity (see pathway vitamin E biosynthesis ). They differ in the number and location of methyl groups on the chromanol ring. The naturally occurring form of a-tocopherol is (2R,4'R,8'R)-a-tocopherol (synonym (R,R,R)-a-tocopherol). Synthetic a-tocopherols are a racemic mixture of eight different R and S stereoisomers. Only the 2R forms are recognized as meeting human requirements. The in vivo function of vitamin E is to scavenge peroxyl radicals via its phenolic (chromanol) hydroxyl group, thus protecting lipids against free radical-catalyzed peroxidation. The tocopheryl radical formed can then be reduced by reductants such as L-ascorbate. Other major products of a-tocopherol oxidation include α-tocopherylquinone and epoxy-a-tocopherols. The metabolites a-tocopheronic acid and its lactone, known as the Simon metabolites, are generally believed to be artefacts. In addition to these oxidation products, the other major class of tocopherol metabolites is the carboxyethyl-hydroxychromans.These metabolites are produced in significant amounts in response to excess vitamin E ingestion. Vitamin E is fat-soluble and its utilization requires intestinal fat absorption mechanisms. It is secreted from the intestine into the lymphatic system in chylomicrons which subsequently enter the plasma. Lipolysis of these chylomicrons can result in delivery of vitamin E to tissues, transfer to high-density lipoproteins (and subsequently to other lipoproteins via the phospholipid exchange protein), or retention in chylomicron remnants. These remnants are taken up by the liver. Natural (R,R,R)-α-tocopherol and synthetic 2R-α-tocopherols are then preferentially secreted from the liver into plasma as a result of the specificity of the α-tocopherol transfer protein. This protein, along with the metabolism of excess vitamin E in the liver and excretion into urine and bile, mediate the supply of a-tocopherol in plasma and tissues.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
13-OH-alpha-Tocopherol	ChEBI
13-OH-a-Tocopherol	Generator
13-OH-Α-tocopherol	Generator
13'-Hydroxy-a-tocopherol	Generator
13'-Hydroxy-α-tocopherol	Generator
13-Hydroxy-a-tocopherol	HMDB
13-Hydroxy-α-tocopherol	HMDB
13'-Hydroxy-alpha-tocopherol	ChEBI

Chemical Formula

C₂₉H₅₀O₃

Average Molecular Weight

446.7055

Monoisotopic Molecular Weight

446.375995466

IUPAC Name

(2R)-2-[(4R,8S)-13-hydroxy-4,8,12-trimethyltridecyl]-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-6-ol

Traditional Name

(2R)-2-[(4R,8S)-13-hydroxy-4,8,12-trimethyltridecyl]-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-6-ol

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C29H50O3/c1-20(13-9-14-22(3)19-30)11-8-12-21(2)15-10-17-29(7)18-16-26-25(6)27(31)23(4)24(5)28(26)32-29/h20-22,30-31H,8-19H2,1-7H3/t20-,21+,22?,29+/m0/s1

InChI Key

URYLCCKXLNXSRS-XIRVVSDESA-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
Long chain fatty alcohol
Chromane
Benzopyran
1-benzopyran
Fatty alcohol
Alkyl aryl ether
Fatty acyl
Benzenoid
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:84962 )
primary alcohol (CHEBI:84962 )
chromanol (CHEBI:84962 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012559)

Source

Endogenous

Endogenous (HMDB: HMDB0012559)

Animal

Animal (HMDB: HMDB0012559)

Exogenous

Food

Food (HMDB: HMDB0012559)

Exogenous (HMDB: HMDB0012559)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012559)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012559)

Lipid metabolism pathway (HMDB: HMDB0012559)

Cellular process

Cell signaling (HMDB: HMDB0012559)

Biochemical process

Lipid transport (HMDB: HMDB0012559)

Role

Biological role

Energy source (HMDB: HMDB0012559)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012559)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.7e-05 g/L	ALOGPS
logP	8.07	ALOGPS
logP	9.15	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	10.8	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	137.23 m³·mol⁻¹	ChemAxon
Polarizability	57.32 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

External Links

HMDB ID

HMDB0012559

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029125

KNApSAcK ID

Not Available

Chemspider ID

34999549

KEGG Compound ID

Not Available

BioCyc ID

CPD-11960

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481465

PDB ID

Not Available

ChEBI ID

84962

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 13'-Hydroxy-alpha-tocopherol (CFc000008035)

MOL for CFc000008035 (13'-Hydroxy-alpha-tocopherol)

3D MOL for CFc000008035 (13'-Hydroxy-alpha-tocopherol)

3D SDF for CFc000008035 (13'-Hydroxy-alpha-tocopherol)

3D-SDF for CFc000008035 (13'-Hydroxy-alpha-tocopherol)

PDB for CFc000008035 (13'-Hydroxy-alpha-tocopherol)

3D PDB for CFc000008035 (13'-Hydroxy-alpha-tocopherol)

SMILES for CFc000008035 (13'-Hydroxy-alpha-tocopherol)

INCHI for CFc000008035 (13'-Hydroxy-alpha-tocopherol)

Structure for CFc000008035 (13'-Hydroxy-alpha-tocopherol)

3D Structure for CFc000008035 (13'-Hydroxy-alpha-tocopherol)