ChemFOnt: Showing chemical card for Canthaxanthin (CFc000001788)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:30 UTC

Chemfont ID

CFc000001788

Molecule Identification

Common Name

Canthaxanthin

Definition

Canthaxanthin, also known as Cantaxanthin, Cantaxanthine, or Canthaxanthine is a keto-carotenoid, a pigment widely distributed in nature. Carotenoids belong to a larger class of phytochemicals known as terpenoids. Canthaxanin is also classified as a xanthophyll. Xanthophylls are yellow pigments and form one of two major divisions of the carotenoid group; the other division is formed by the carotenes. Both are carotenoids. Xanthophylls and carotenes are similar in structure, but xanthophylls contain oxygen atoms while carotenes are purely hydrocarbons, which do not contain oxygen. Their content of oxygen causes xanthophylls to be more polar (in molecular structure) than carotenes and causes their separation from carotenes in many types of chromatography. (Carotenes are usually more orange in color than xanthophylls. Canthaxanthin is naturally found in bacteria, algae and some fungi. Canthaxanthin is associated with E number E161g and is approved for use as a food coloring agent in different countries, including the United States and the EU. Canthaxanthin is used as poultry feed additive to yield red color in skin and yolks. The European Union permits the use of canthaxanthin in feedstuff at a maximum content of 25 mg/kg of final feedstuff while the United States allows the use of this pigment in broiler chicken and salmonid fish feeds. Canthoxanthin was first isolated in edible chanterelle mushroom (Cantharellus cinnabarinus), from which it derived its name. It has also been found in green algae, bacteria, archea (a halophilic archaeon called Haloferax alexandrines), fungi and bioaccumulates in tissues and egg yolk from wild birds and at low levels in crustaceans and fish such as carp, golden grey mullet, and seabream. Canthaxanthin is not found in wild Atlantic Salmon, but is a minor carotenoid in Pacific Salmon. Canthaxanthin is used in farm-raised trout to give a red/orange color to their flesh similar to wild trout. Canthaxanthin has been used as a food additive for egg yolk, in cosmetics and as a pigmenting agent for human skin applications. It has also been used as a feed additive in fish and crustacean farms. Canthaxanthin is a potent lipid-soluble antioxidant (PMID: 2505240 ). Canthaxanthin increases resistance to lipid peroxidation primarily by enhancing membrane alpha-tocopherol levels and secondarily by providing weak direct antioxidant activity. Canthaxanthin biosynthesis in bacteria and algae proceeds from beta-carotene via the action of an enzyme known as a beta-carotene ketolase, that is able to add a carbonyl group to carbon 4 and 4' of the beta carotene molecule.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄₀H₅₂O₂

Average Molecular Weight

564.8397

Monoisotopic Molecular Weight

564.396730908

IUPAC Name

2,4,4-trimethyl-3-[(1Z,3Z,5E,7E,9Z,11E,13E,15Z,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one

Traditional Name

2,4,4-trimethyl-3-[(1Z,3Z,5E,7E,9Z,11E,13E,15Z,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one

CAS Registry Number

514-78-3

SMILES

[H]\C(=C(/[H])\C(\[H])=C(/C)C([H])=C([H])C(\[H])=C(\C)/C(/[H])=C(/[H])C1=C(C)C(=O)CCC1(C)C)C([H])=C(C)C(\[H])=C(/[H])\C(\[H])=C(\C)C([H])=C([H])C1=C(C)C(=O)CCC1(C)C

InChI Identifier

InChI=1S/C40H52O2/c1-29(17-13-19-31(3)21-23-35-33(5)37(41)25-27-39(35,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-36-34(6)38(42)26-28-40(36,9)10/h11-24H,25-28H2,1-10H3/b12-11-,17-13+,18-14+,23-21-,24-22+,29-15+,30-16+,31-19-,32-20-

InChI Key

FDSDTBUPSURDBL-MFMWEGPCSA-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
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8895059)

Tissue

Epithelium

Epidermis (HMDB: HMDB0003154)

Cellular substructure

Membrane (HMDB: HMDB0003154)
Extracellular (HMDB: HMDB0003154)

Source

Exogenous

Exogenous (HMDB: HMDB0003154)

Fishes (FooDB: FOOD00865)

Crustacean

Crustaceans (FooDB: FOOD00862)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00046 g/L	ALOGPS
logP	8.71	ALOGPS
logP	9.79	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	19.59	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	193 m³·mol⁻¹	ChemAxon
Polarizability	70.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015890

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Canthaxanthin

METLIN ID

Not Available

PubChem Compound

124511599

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Canthaxanthin (CFc000001788)

MOL for CFc000001788 (Canthaxanthin)

3D MOL for CFc000001788 (Canthaxanthin)

3D SDF for CFc000001788 (Canthaxanthin)

3D-SDF for CFc000001788 (Canthaxanthin)

PDB for CFc000001788 (Canthaxanthin)

3D PDB for CFc000001788 (Canthaxanthin)

SMILES for CFc000001788 (Canthaxanthin)

INCHI for CFc000001788 (Canthaxanthin)

Structure for CFc000001788 (Canthaxanthin)

3D Structure for CFc000001788 (Canthaxanthin)