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Details

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
Structure of CANTHAXANTHIN

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+

HIDE SMILES / InChI

Molecular Formula C40H52O2
Molecular Weight 564.8397
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 9
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6432595 | https://www.ncbi.nlm.nih.gov/pubmed/3935496 | https://www.ncbi.nlm.nih.gov/pubmed/6819749 | https://www.ncbi.nlm.nih.gov/pubmed/22770743

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Psoriasis and vitamin A. Plasma transport and skin content of retinol, dehydroretinol and carotenoids in adult patients versus healthy controls.
1985
Plasma concentrations of beta-carotene and canthaxanthin during and after stopping intake of a combined preparation.
1985
Aplastic anemia associated with canthaxanthin ingested for 'tanning' purposes.
1990 Sep 5
Ah receptor-dependent CYP1A induction by two carotenoids, canthaxanthin and beta-apo-8'-carotenal, with no affinity for the TCDD binding site.
1997 Jul 15
Interactions in the postprandial appearance of beta-carotene and canthaxanthin in plasma triacylglycerol-rich lipoproteins in humans.
1997 Nov
Ocular side effects from herbal medicines and nutritional supplements.
2004 Oct
A study in scarlet: enzymes of ketocarotenoid biosynthesis in the flowers of Adonis aestivalis.
2005 Feb
Patents

Sample Use Guides

In Vivo Use Guide
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:18:44 GMT 2023
Edited
by admin
on Fri Dec 15 15:18:44 GMT 2023
Record UNII
4C3C6403MU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CANTHAXANTHIN
FCC   MART.   MI   WHO-DD  
Common Name English
CANTHAXANTHIN [MI]
Common Name English
ALL-TRANS-CANTHAXANTHIN
Common Name English
CANTHAXANTHIN [FCC]
Common Name English
CAROPHYLL RED
Common Name English
CANTHAXANTHIN (E 161G)
Common Name English
INS-161G
Code English
FOOD ORANGE 8
Common Name English
KANTAKISANTIN
Brand Name English
CI 40850
INCI  
INCI  
Official Name English
CANTHAXANTHIN [MART.]
Common Name English
CI 40850 [INCI]
Common Name English
Canthaxanthin [WHO-DD]
Common Name English
INS NO.161G
Code English
NSC-374110
Code English
E-161G
Code English
ROXANTHIN RED 10
Common Name English
CANTHA
Common Name English
LUCANTIN RED
Common Name English
CI-(1975)NO.40850
Code English
4,4'-DIKETO-.BETA.-CAROTENE
Common Name English
CI-FOOD ORANGE 8
Common Name English
.BETA.-CAROTENE-4,4'-DIONE
Common Name English
Classification Tree Code System Code
CODEX ALIMENTARIUS (GSFA) INS-161G
Created by admin on Fri Dec 15 15:18:44 GMT 2023 , Edited by admin on Fri Dec 15 15:18:44 GMT 2023
DSLD 1037 (Number of products:1)
Created by admin on Fri Dec 15 15:18:44 GMT 2023 , Edited by admin on Fri Dec 15 15:18:44 GMT 2023
JECFA EVALUATION INS-161G
Created by admin on Fri Dec 15 15:18:44 GMT 2023 , Edited by admin on Fri Dec 15 15:18:44 GMT 2023
Code System Code Type Description
MERCK INDEX
m3026
Created by admin on Fri Dec 15 15:18:44 GMT 2023 , Edited by admin on Fri Dec 15 15:18:44 GMT 2023
PRIMARY Merck Index
SMS_ID
100000076626
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PRIMARY
NSC
374110
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PRIMARY
EVMPD
SUB13228MIG
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PRIMARY
NCI_THESAURUS
C68309
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PRIMARY
RXCUI
42348
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PRIMARY RxNorm
EPA CompTox
DTXSID0022727
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PRIMARY
FDA UNII
4C3C6403MU
Created by admin on Fri Dec 15 15:18:44 GMT 2023 , Edited by admin on Fri Dec 15 15:18:44 GMT 2023
PRIMARY
CAS
514-78-3
Created by admin on Fri Dec 15 15:18:44 GMT 2023 , Edited by admin on Fri Dec 15 15:18:44 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-187-2
Created by admin on Fri Dec 15 15:18:44 GMT 2023 , Edited by admin on Fri Dec 15 15:18:44 GMT 2023
PRIMARY
WIKIPEDIA
CANTHAXANTHIN
Created by admin on Fri Dec 15 15:18:44 GMT 2023 , Edited by admin on Fri Dec 15 15:18:44 GMT 2023
PRIMARY
MESH
D016644
Created by admin on Fri Dec 15 15:18:44 GMT 2023 , Edited by admin on Fri Dec 15 15:18:44 GMT 2023
PRIMARY
CHEBI
3362
Created by admin on Fri Dec 15 15:18:44 GMT 2023 , Edited by admin on Fri Dec 15 15:18:44 GMT 2023
PRIMARY
PUBCHEM
5281227
Created by admin on Fri Dec 15 15:18:44 GMT 2023 , Edited by admin on Fri Dec 15 15:18:44 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY