Stereochemistry | ACHIRAL |
Molecular Formula | C40H52O2 |
Molecular Weight | 564.8397 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 9 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(\C=C\C=C(C)\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)CCC2(C)C
InChI
InChIKey=FDSDTBUPSURDBL-DKLMTRRASA-N
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+
Molecular Formula | C40H52O2 |
Molecular Weight | 564.8397 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 9 |
Optical Activity | NONE |
Canthaxanthin is a keto-carotenoid pigment and potent lipid-soluble antioxidant widely distributed in nature. Canthaxanthin has been found in edible mushrooms green algae, bacteria, crustaceans, and bioaccumulates in fish such as carp, golden mullet, seabream and trash wrasse. Canthaxanthin is used to reduce sensitivity to sunlight (photosensitivity) experienced by people who have a rare genetic disease called erythropoietic protoporphyria (EPP). In these people, sunlight can cause skin reactions such as rash, itch, and eczema. Canthaxanthin is also used to reduce sun sensitivity caused by certain medications. Some people also try it for relieving itching caused by sun exposure. 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; however, it is not approved for use in Australia and New Zealand. It is generally authorized for feed applications in at least the following countries: US, Canada, EU. In the EU, canthaxanthin is allowed by law to be added to trout feed, salmon feed, and poultry feed. The European Union limit is 80 mg/kg of feedstuffs, 8 mg/kg feed for egg-laying hens and 25 mg/kg in feed for other poultry and salmonids.
Originator
Approval Year
Sample Use Guides
For reducing and treating rash, itch, and/or eczema (symptoms of photosensitivity) in people with erythropoietic protoporphyria (EPP) when they are exposed to sunlight: 60 to 90 mg of canthaxanthin daily on average for three to five months per year.
Route of Administration:
Oral
Caco-2 cells (2 x 10^3 cells/well in 96-well plates) were incubated at 37 ◦C until a confluent monolayer was formed (after 4–6 days). Then cells were pre-incubated for 30 min at 37C with different concentrations of Canthaxanthin (1-200mkM). Verapamil was used as a positive substrate control. Cells were then incubated for 90 min with either rhodamine 123 (Rho123) (1 mkg/ml), or calcein-AM (150 nM); afterwards they were washed with substrate free medium. Rho123 and calcein fluorescence was measured at excitation/emission wavelengths of 485/535 nm using Tecan Safire IITM spectrofluorometer (Tecan Crailsheim, Germany). The same protocol was applied by using different concentrations of the substrate doxorubicin with and without selected carotenoids (40 mkM); fluorescence of doxorubicin was measured at excitation/emission wavelengths of 480/590.