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Canthaxanthin

CAS# 514-78-3

Canthaxanthin

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Chemical structure

Canthaxanthin

3D structure

Chemical Properties of Canthaxanthin

Cas No. 514-78-3 SDF Download SDF
PubChem ID 5281227 Appearance Powder
Formula C40H52O2 M.Wt 564.8
Type of Compound N/A Storage Desiccate at -20°C
Synonyms E 161g; all-trans-Canthaxanthin
Solubility DMSO : 1 mg/mL (1.77 mM; ultrasonic and warming and heat to 80°C)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name 2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-2-en-1-one
SMILES CC1=C(C(CCC1=O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2=C(C(=O)CCC2(C)C)C)C)C
Standard InChIKey FDSDTBUPSURDBL-DKLMTRRASA-N
Standard InChI 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+
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Protocol

Animal Administration [3]
Mice: Female 6-wk-old Balb/c mice are randomly divided into two groups (n = 10/group). The control group receives olive oil alone (vehicle) and the canthaxanthin-treated group receives canthaxanthin at a dose of 14 μg/kg body weight per day. At the end of the treatment, mice are killed by cervical dislocation and liver is excised, frozen in liquid nitrogen and stored at −80°C[3].

References:
[1]. Esatbeyoglu T, et al. Canthaxanthin: From molecule to function. Mol Nutr Food Res. 2017 Jun;61(6). [2]. Huang DS, et al. Inhibitory effects of canthaxanthin on in vitro growth of murine tumor cells. Cancer Lett. 1992 Aug 31;65(3):209-13. [3]. Palozza P, et al. Canthaxanthin supplementation alters antioxidant enzymes and iron concentration in liver of Balb/c mice. J Nutr. 2000 May;130(5):1303-8. [4]. Chew BP, et al. A comparison of the anticancer activities of dietary beta-carotene, canthaxanthin and astaxanthin in mice in vivo. Anticancer Res. 1999 May-Jun;19(3A):1849-53. [5]. Grubbs CJ, et al. Effect of canthaxanthin on chemically induced mammary carcinogenesis. Oncology. 1991;48(3):239-45.

Canthaxanthin Dilution Calculator

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Canthaxanthin Molarity Calculator

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Preparing Stock Solutions of Canthaxanthin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.7705 mL 8.8527 mL 17.7054 mL 35.4108 mL 44.2635 mL
5 mM 0.3541 mL 1.7705 mL 3.5411 mL 7.0822 mL 8.8527 mL
10 mM 0.1771 mL 0.8853 mL 1.7705 mL 3.5411 mL 4.4263 mL
50 mM 0.0354 mL 0.1771 mL 0.3541 mL 0.7082 mL 0.8853 mL
100 mM 0.0177 mL 0.0885 mL 0.1771 mL 0.3541 mL 0.4426 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Canthaxanthin

Canthaxanthin is a red-orange carotenoid with various biological activities, such as antioxidant, antitumor properties.

In Vitro:Canthaxanthin enrichment of LDL has the potential to protect cholesterol from oxidation. In addition to its free radical scavenging and antioxidant properties (e.g., the induction of catalase and superoxide dismutase), canthaxanthin shows immunomodulatory activity (e.g. enhancing the proliferation and function of immune competent cells) and plays important role in gap junction communication (e.g. induction of the transmembrane protein connexin)[1]. At concentrations of 0.1 to 1 x 1000 μM, canthaxanthin significantly reduces the overall number of tumor cells. The greatest inhibition is observed at a canthaxanthin concentration of 1000 after 72 h and 96 h of incubation[2].

In Vivo:Canthaxanthin alters the protective ability of tissues against oxidative stress. Canthaxanthin treatment for 15 d at the dose of 14 μg/kg body weight results in hepatic incorporation of the carotenoid, which is maximum in liver and reaches 0.52 ± 0.05 nmol/g liver. Glutathione peroxidase activity is 35% lower and catalase (59%) and manganese superoxide dismutase (28%) activities are higher in canthaxanthin-treated mice than in controls[3]. Canthaxanthin inhibit the growth of mammary tumors in mice and the anti-tumor activity is also influenced by the supplemental dose[4]. Diet supplementation with canthaxanthin for 3 weeks prior to the carcinogen results in a 65% reduction in the number of mammary cancers by a mechanism not involving pro-vitamin A activity[5].

References:
[1]. Esatbeyoglu T, et al. Canthaxanthin: From molecule to function. Mol Nutr Food Res. 2017 Jun;61(6). [2]. Huang DS, et al. Inhibitory effects of canthaxanthin on in vitro growth of murine tumor cells. Cancer Lett. 1992 Aug 31;65(3):209-13. [3]. Palozza P, et al. Canthaxanthin supplementation alters antioxidant enzymes and iron concentration in liver of Balb/c mice. J Nutr. 2000 May;130(5):1303-8. [4]. Chew BP, et al. A comparison of the anticancer activities of dietary beta-carotene, canthaxanthin and astaxanthin in mice in vivo. Anticancer Res. 1999 May-Jun;19(3A):1849-53. [5]. Grubbs CJ, et al. Effect of canthaxanthin on chemically induced mammary carcinogenesis. Oncology. 1991;48(3):239-45.

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References on Canthaxanthin

Retinal toxicity due to canthaxanthin. Case series.[Pubmed:29573837]

Arch Soc Esp Oftalmol. 2018 Aug;93(8):411-415.

INTRODUCTION: Canthaxanthin is a chemical product used to tan the skin. Its most frequent adverse effect is Canthaxanthin retinopathy. PURPOSE/ METHODS: Report, case series. RESULTS: Two female patients, one 42 years-old and the other 72 years-old, with signs of retinopathy due to Canthaxanthin. Complete ophthalmology examinations were carried out. The peripheral fovea birefringent deposits with internal retinal involvement were studied using multimodal imaging. CONCLUSION: Canthaxanthin retinopathy is rare. Multimodal imaging may provide important data for the differential diagnosis of crystalline retinopathy.

Description

Canthaxanthin is a red-orange carotenoid with various biological activities, such as antioxidant, antitumor properties.

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