Canthaxanthin
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MedKoo CAT#: 597684

CAS#: 514-78-3

Description: Canthaxanthin is a trans-carotenoid pigment widely distributed in nature. The compound is used as an oral suntanning agent and as a food and drug coloring agent. Oral ingestion of the compound causes canthaxanthin retinopathy.


Chemical Structure

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Canthaxanthin
CAS# 514-78-3

Theoretical Analysis

MedKoo Cat#: 597684
Name: Canthaxanthin
CAS#: 514-78-3
Chemical Formula: C40H52O2
Exact Mass: 564.3967
Molecular Weight: 564.85
Elemental Analysis: C, 85.06; H, 9.28; O, 5.66

Price and Availability

Size Price Availability Quantity
10.0mg USD 300.0 2 Weeks
25.0mg USD 680.0 2 Weeks
100.0mg USD 1280.0 2 Weeks
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Synonym: Canthaxanthin; CI 40850; E 161 G; Ro 1-9915; C.I. Food Orange 8;

IUPAC/Chemical Name: 3,3'-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl)bis(2,4,4-trimethylcyclohex-2-en-1-one)

InChi Key: FDSDTBUPSURDBL-DKLMTRRASA-N

InChi Code: 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+

SMILES Code: CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C(C(C)(C)CC2)=C(C)C2=O)C(C)(C)CCC1=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

Product Data:

Biological target: Canthaxanthin is a red-orange carotenoid with various biological activities, such as antioxidant, antitumor properties.
In vitro activity: The antitumorigenic effects of carotenoids, in addition to their immuno-enhancing effects, may occur by their direct action on growing tumor cells. To test this hypothesis the direct inhibitory effect of various concentrations of canthaxanthin (CX; 4,4'-diketo-beta-carotene), a non-provitamin A carotenoid, was tested on the in vitro growth of JB/MS, B16F10 melanomas and PYB6 fibrosarcoma and murine non-transformed NIH-3T3 (ATCC CRL 1658) cells. At concentrations of 1 x 10(-8) M up to 1 x 10(-4) M, CX significantly reduced the overall number of tumor cells. The greatest inhibition was observed at a CX concentration of 1 x 10(-4) M after 72 h and 96 h of incubation. However, CX had no inhibitory effect on the growth of the non-transformed NIH-3T3 cell line; rather it significantly enhanced growth of this cell line (P less than 0.05) after 96 h of incubation. Thus, the inhibitory action of CX on growing tumor cells appears to be due to its direct actions on tumor cells and not via its conversion to vitamin A or its immuno-enhancing effects. Reference: Cancer Lett. 1992 Aug 31;65(3):209-13. https://linkinghub.elsevier.com/retrieve/pii/0304-3835(92)90233-L
In vivo activity: The 4,4'-diketo-beta-carotene, canthaxanthin, alters tocopherol status when fed to Balb/c mice, suggesting an involvement of carotenoids in the modulation of oxidative stress in vivo. We investigated further the modifications induced by an oral administration of canthaxanthin on lipid peroxidation, antioxidant enzymes and iron status in liver of Balb/c mice. Female 6-wk-old Balb/c mice were randomly divided into two groups (n = 10/group). The control group (C) received olive oil alone (vehicle) and the canthaxanthin-treated group (Cx) received canthaxanthin at a dose of 14 microg/(g body wt.d). The 15-d canthaxanthin treatment resulted in carotenoid incorporation but did not modify lipid peroxidation as measured by endogenous production of malondialdehyde (MDA). However, glutathione peroxidase activity was 35% lower (P<0.01) and catalase (59%, P<0.005) and manganese superoxide dismutase (MnSOD) (28%, P<0.05) activities were higher in canthaxanthin-treated mice than in controls. Moreover, carotenoid feeding caused a significant (P<0.05) overexpression of the MnSOD gene; mRNA levels of the enzyme were greater in treated mice than in controls. Concomitantly, a 27% (P<0.05) greater iron concentration was found in liver from canthaxanthin-treated mice compared with controls. These findings support the hypothesis that canthaxanthin alters the protective ability of tissues against oxidative stress in vivo. Reference: J Nutr. 2000 May;130(5):1303-8. https://academic.oup.com/jn/article-lookup/doi/10.1093/jn/130.5.1303

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 1.0 1.77

Preparing Stock Solutions

The following data is based on the product molecular weight 564.85 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
In vitro protocol: 1. Huang DS, Odeleye OE, Watson RR. Inhibitory effects of canthaxanthin on in vitro growth of murine tumor cells. Cancer Lett. 1992 Aug 31;65(3):209-13. doi: 10.1016/0304-3835(92)90233-l. PMID: 1516035. 2. Esatbeyoglu T, Rimbach G. Canthaxanthin: From molecule to function. Mol Nutr Food Res. 2017 Jun;61(6). doi: 10.1002/mnfr.201600469. Epub 2016 Nov 15. PMID: 27687695.
In vivo protocol: 1. Palozza P, Calviello G, Emilia De Leo M, Serini S, Bartoli GM. Canthaxanthin supplementation alters antioxidant enzymes and iron concentration in liver of Balb/c mice. J Nutr. 2000 May;130(5):1303-8. doi: 10.1093/jn/130.5.1303. PMID: 10801934. 2. Esatbeyoglu T, Rimbach G. Canthaxanthin: From molecule to function. Mol Nutr Food Res. 2017 Jun;61(6). doi: 10.1002/mnfr.201600469. Epub 2016 Nov 15. PMID: 27687695.

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1: Papp T, Csernetics A, Nagy G, Bencsik O, Iturriaga EA, Eslava AP, Vágvölgyi C. Canthaxanthin production with modified Mucor circinelloides strains. Appl Microbiol Biotechnol. 2013 Jun;97(11):4937-50. doi: 10.1007/s00253-012-4610-2. Epub 2012 Dec 9. PubMed PMID: 23224586.

2: Mordi RC, Walton JC. Identification of products from canthaxanthin oxidation. Food Chem. 2016 Apr 15;197(Pt A):836-40. doi: 10.1016/j.foodchem.2015.11.053. Epub 2015 Nov 12. PubMed PMID: 26617024.

3: Grama BS, Chader S, Khelifi D, Agathos SN, Jeffryes C. Induction of canthaxanthin production in a Dactylococcus microalga isolated from the Algerian Sahara. Bioresour Technol. 2014 Jan;151:297-305. doi: 10.1016/j.biortech.2013.10.073. Epub 2013 Nov 1. PubMed PMID: 24262839.

4: Sujak A. Exceptional molecular organization of canthaxanthin in lipid membranes. Acta Biochim Pol. 2012;59(1):31-3. Epub 2012 Mar 17. Review. PubMed PMID: 22428120.

5: Gharibzahedi SM, Razavi SH, Mousavi M. Characterizing the natural canthaxanthin/2-hydroxypropyl-β-cyclodextrin inclusion complex. Carbohydr Polym. 2014 Jan 30;101:1147-53. doi: 10.1016/j.carbpol.2013.10.074. Epub 2013 Oct 27. PubMed PMID: 24299886.

6: Grama BS, Delhaye A, Chader S, Khelifi D, Agathos S, Jeffryes C. Canthaxanthin, astaxanthin and adonixanthin production from a dactylococcus microalga in a new flat plate airlift photobioreactor. Commun Agric Appl Biol Sci. 2014;79(1):65-70. PubMed PMID: 25864315.

7: Rostami F, Razavi SH, Sepahi AA, Gharibzahedi SM. Canthaxanthin biosynthesis by Dietzia natronolimnaea HS-1: effects of inoculation and aeration rate. Braz J Microbiol. 2014 Aug 29;45(2):447-56. eCollection 2014. PubMed PMID: 25242927; PubMed Central PMCID: PMC4166268.

8: Zhou X, Xie JR, Tao L, Xin ZJ, Zhao FW, Lu XH, Zhao MR, Wang L, Liang JP. The effect of microdosimetric 12C6+ heavy ion irradiation and Mg2+ on canthaxanthin production in a novel strain of Dietzia natronolimnaea. BMC Microbiol. 2013 Sep 28;13:213. doi: 10.1186/1471-2180-13-213. PubMed PMID: 24074304; PubMed Central PMCID: PMC3849488.

9: Gao Y, Xu D, Kispert LD. Hydrogen Bond Formation between the Carotenoid Canthaxanthin and the Silanol Group on MCM-41 Surface. J Phys Chem B. 2015 Aug 20;119(33):10488-95. doi: 10.1021/acs.jpcb.5b05645. Epub 2015 Aug 10. PubMed PMID: 26230844.

10: Veiga-Crespo P, Vinuesa T, Viñas M, Villa TG. Analysis of canthaxanthin production by Gordonia jacobaea. Methods Mol Biol. 2012;892:159-72. doi: 10.1007/978-1-61779-879-5_8. PubMed PMID: 22623301.

11: Hojjati M, Razavi SH, Rezaei K, Gilani K. Stabilization of canthaxanthin produced by Dietzia natronolimnaea HS-1 with spray drying microencapsulation. J Food Sci Technol. 2014 Sep;51(9):2134-40. doi: 10.1007/s13197-012-0713-0. Epub 2012 May 5. PubMed PMID: 25190874; PubMed Central PMCID: PMC4152546.

12: Chang CS, Chang CL, Lai GH. Reactive oxygen species scavenging activities in a chemiluminescence model and neuroprotection in rat pheochromocytoma cells by astaxanthin, beta-carotene, and canthaxanthin. Kaohsiung J Med Sci. 2013 Aug;29(8):412-21. doi: 10.1016/j.kjms.2012.12.002. Epub 2013 Feb 8. PubMed PMID: 23906231.

13: Schöpf L, Mautz J, Sandmann G. Multiple ketolases involved in light regulation of canthaxanthin biosynthesis in Nostoc punctiforme PCC 73102. Planta. 2013 May;237(5):1279-85. doi: 10.1007/s00425-013-1846-8. Epub 2013 Jan 30. PubMed PMID: 23361890.

14: Rosa AP, Scher A, Sorbara JO, Boemo LS, Forgiarini J, Londero A. Effects of canthaxanthin on the productive and reproductive performance of broiler breeders. Poult Sci. 2012 Mar;91(3):660-6. doi: 10.3382/ps.2011-01582. PubMed PMID: 22334741.

15: Zheng YF, Bae SH, Kwon MJ, Park JB, Choi HD, Shin WG, Bae SK. Inhibitory effects of astaxanthin, β-cryptoxanthin, canthaxanthin, lutein, and zeaxanthin on cytochrome P450 enzyme activities. Food Chem Toxicol. 2013 Sep;59:78-85. doi: 10.1016/j.fct.2013.04.053. Epub 2013 May 11. PubMed PMID: 23669408.

16: Yuri T, Yoshizawa K, Emoto Y, Kinoshita Y, Yuki M, Tsubura A. Effects of Dietary Xanthophylls, Canthaxanthin and Astaxanthin on N-Methyl-N-nitrosourea-induced Rat Mammary Carcinogenesis. In Vivo. 2016 11-12;30(6):795-800. PubMed PMID: 27815463.

17: Niu J, Li CH, Liu YJ, Tian LX, Chen X, Huang Z, Lin HZ. Dietary values of astaxanthin and canthaxanthin in Penaeus monodon in the presence and absence of cholesterol supplementation: effect on growth, nutrient digestibility and tissue carotenoid composition. Br J Nutr. 2012 Jul 14;108(1):80-91. doi: 10.1017/S0007114511005423. Epub 2011 Dec 6. PubMed PMID: 22142867.

18: Brizio P, Benedetto A, Righetti M, Prearo M, Gasco L, Squadrone S, Abete MC. Astaxanthin and canthaxanthin (xanthophyll) as supplements in rainbow trout diet: in vivo assessment of residual levels and contributions to human health. J Agric Food Chem. 2013 Nov 20;61(46):10954-9. doi: 10.1021/jf4012664. Epub 2013 Nov 5. PubMed PMID: 24156372.

19: Venugopalan V, Tripathi SK, Nahar P, Saradhi PP, Das RH, Gautam HK. Characterization of canthaxanthin isomers isolated from a new soil Dietzia sp. and their antioxidant activities. J Microbiol Biotechnol. 2013 Feb;23(2):237-45. PubMed PMID: 23412067.

20: Gharibzahedi SM, Razavi SH, Mousavi M. Feeding strategies for the improved biosynthesis of canthaxanthin from enzymatic hydrolyzed molasses in the fed-batch fermentation of Dietzia natronolimnaea HS-1. Bioresour Technol. 2014 Feb;154:51-8. doi: 10.1016/j.biortech.2013.12.013. Epub 2013 Dec 11. PubMed PMID: 24384310.