ChemFOnt: Showing chemical card for 5,6-Dihydro-b,b-carotene-3,3',5,6-tetrol (CFc000336873)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:16 UTC

Chemfont ID

CFc000336873

Molecule Identification

Common Name

5,6-Dihydro-b,b-carotene-3,3',5,6-tetrol

Definition

6-epikarpoxanthin is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. 6-epikarpoxanthin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 6-epikarpoxanthin can be found in a number of food items such as italian sweet red pepper, herbs and spices, fruits, and orange bell pepper, which makes 6-epikarpoxanthin a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3S,3'r,5R,6S)-5,6-dihydro-3,3',5,6-Tetrahydroxy-beta,beta-carotene	HMDB
6-Epiheteroxanthin	HMDB

Chemical Formula

C₄₀H₅₈O₄

Average Molecular Weight

602.8861

Monoisotopic Molecular Weight

602.433510344

IUPAC Name

1-[(1E,3E,5Z,7E,9E,11Z,13Z,15Z,17Z)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,6,6-trimethylcyclohexane-1,2,4-triol

Traditional Name

1-[(1E,3E,5Z,7E,9E,11Z,13Z,15Z,17Z)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,6,6-trimethylcyclohexane-1,2,4-triol

CAS Registry Number

24204-13-5

SMILES

C\C(\C=C/C=C(/C)\C=C/C1=C(C)CC(O)CC1(C)C)=C\C=C\C=C(/C)\C=C/C=C(\C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O

InChI Identifier

InChI=1S/C40H58O4/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40(44)38(8,9)27-35(42)28-39(40,10)43/h11-24,34-35,41-44H,25-28H2,1-10H3/b12-11+,17-13-,18-14-,22-21-,24-23+,29-15-,30-16+,31-19-,32-20+

InChI Key

DJOWTWWHMWQATC-BXBIEBEISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Cyclohexanol
Cyclitol or derivatives
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034978)

Source

Endogenous

Endogenous (HMDB: HMDB0034978)

Plant

Plant (HMDB: HMDB0034978)

Animal

Animal (HMDB: HMDB0034978)

Exogenous

Food

Food (HMDB: HMDB0034978)

Vegetable

Fruit vegetable

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034978)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034978)

Lipid metabolism pathway (HMDB: HMDB0034978)

Cellular process

Cell signaling (HMDB: HMDB0034978)

Biochemical process

Lipid transport (HMDB: HMDB0034978)

Role

Biological role

Energy source (HMDB: HMDB0034978)

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0034978)

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034978)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0011 g/L	ALOGPS
logP	7	ALOGPS
logP	6.64	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	12.91	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	197.15 m³·mol⁻¹	ChemAxon
Polarizability	74.19 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

HMDB0034978

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021644

KNApSAcK ID

C00022927

Chemspider ID

35013808

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751644

PDB ID

Not Available

ChEBI ID

176201

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 5,6-Dihydro-b,b-carotene-3,3',5,6-tetrol (CFc000336873)

MOL for CFc000336873 (5,6-Dihydro-b,b-carotene-3,3',5,6-tetrol)

3D MOL for CFc000336873 (5,6-Dihydro-b,b-carotene-3,3',5,6-tetrol)

3D SDF for CFc000336873 (5,6-Dihydro-b,b-carotene-3,3',5,6-tetrol)

3D-SDF for CFc000336873 (5,6-Dihydro-b,b-carotene-3,3',5,6-tetrol)

PDB for CFc000336873 (5,6-Dihydro-b,b-carotene-3,3',5,6-tetrol)

3D PDB for CFc000336873 (5,6-Dihydro-b,b-carotene-3,3',5,6-tetrol)

SMILES for CFc000336873 (5,6-Dihydro-b,b-carotene-3,3',5,6-tetrol)

INCHI for CFc000336873 (5,6-Dihydro-b,b-carotene-3,3',5,6-tetrol)

Structure for CFc000336873 (5,6-Dihydro-b,b-carotene-3,3',5,6-tetrol)

3D Structure for CFc000336873 (5,6-Dihydro-b,b-carotene-3,3',5,6-tetrol)