ChemFOnt: Showing chemical card for 9'-Carboxy-alpha-chromanol (CFc000008100)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:44 UTC

Chemfont ID

CFc000008100

Molecule Identification

Common Name

9'-Carboxy-alpha-chromanol

Definition

9'-carboxy-alpha-tocopherol is a dehydrogenation carboxylate product of 9'-hydroxy-a-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
9'-Carboxy-alpha-tocopherol	HMDB
(6S)-9-[(2S)-6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnonanoate	Generator

Chemical Formula

C₂₄H₃₈O₄

Average Molecular Weight

390.5561

Monoisotopic Molecular Weight

390.277009704

IUPAC Name

(6S)-9-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid

Traditional Name

(6S)-9-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C24H38O4/c1-15(9-7-11-16(2)23(26)27)10-8-13-24(6)14-12-20-19(5)21(25)17(3)18(4)22(20)28-24/h15-16,25H,7-14H2,1-6H3,(H,26,27)/t15-,16?,24-/m0/s1

InChI Key

CUGVBZDXUTZXJO-GCIQOJCMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
Medium-chain fatty acid
Alkyl aryl ether
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0012866)
Cell membrane (HMDB: HMDB0012866)

Source

Endogenous

Endogenous (HMDB: HMDB0012866)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00058 g/L	ALOGPS
logP	5.67	ALOGPS
logP	7.38	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	114.11 m³·mol⁻¹	ChemAxon
Polarizability	47.16 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012866

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029190

KNApSAcK ID

Not Available

Chemspider ID

35032551

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481534

PDB ID

Not Available

ChEBI ID

175124

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 9'-Carboxy-alpha-chromanol (CFc000008100)

MOL for CFc000008100 (9'-Carboxy-alpha-chromanol)

3D MOL for CFc000008100 (9'-Carboxy-alpha-chromanol)

3D SDF for CFc000008100 (9'-Carboxy-alpha-chromanol)

3D-SDF for CFc000008100 (9'-Carboxy-alpha-chromanol)

PDB for CFc000008100 (9'-Carboxy-alpha-chromanol)

3D PDB for CFc000008100 (9'-Carboxy-alpha-chromanol)

SMILES for CFc000008100 (9'-Carboxy-alpha-chromanol)

INCHI for CFc000008100 (9'-Carboxy-alpha-chromanol)

Structure for CFc000008100 (9'-Carboxy-alpha-chromanol)

3D Structure for CFc000008100 (9'-Carboxy-alpha-chromanol)