Canthaxanthin

Names

[ CAS No. ]:
514-78-3

[ Name ]:
Canthaxanthin

[Synonym ]:
MFCD00016364
β,β-Carotene-4,4'-dione, (7cis,9cis,11cis,13cis)-
(7cis,9cis,11cis,13cis)-β,β-Carotene-4,4'-dione
Canthaxanthin
all-trans-Canthaxanthin
EINECS 208-187-2

Biological Activity

[Description]:

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

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Terpenoids and Glycosides

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

[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].

[Animal admin]

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.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
717.0±40.0 °C at 760 mmHg

[ Molecular Formula ]:
C₄₀H₅₂O₂

[ Molecular Weight ]:
564.840

[ Flash Point ]:
253.9±24.3 °C

[ Exact Mass ]:
564.396729

[ PSA ]:
34.14000

[ LogP ]:
10.69

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.575

[ Storage condition ]:
0-6°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FI0330000

CHEMICAL NAME :: beta-Carotene-4,4'-dione, all-trans-

CAS REGISTRY NUMBER :: 514-78-3

BEILSTEIN REFERENCE NO. :: 1898520

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C40-H52-O2

MOLECULAR WEIGHT :: 564.92

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 86 mg/kg/15W-I

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - retinal changes (pigmentary depositions, retinitis, other)

REFERENCE :: MJAUAJ Medical Journal of Australia. (Australasian Medical Pub. Co. Ltd., 71-79 Arundel St., Glebe, N.S.W., Australia) V.1- 1914- Volume(issue)/page/year: 143,622,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: SCPHA4 Scientia Pharmaceutica. (Oesterreichische Apotheker-Verlagsgesellschaft MBH, Spitalgasse 31, 1094 Vienna 9, Austria) V.1- 1930- Volume(issue)/page/year: 47,39,1979

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Risk Phrases ]:
25-36/37/38

[ Safety Phrases ]:
45-36/37/39-28A-26

[ RIDADR ]:
UN 2811 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
GA0875000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1

[ HS Code ]:
3204199000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 3204199000

Articles

Developing an emulsion model system containing canthaxanthin biosynthesized by Dietzia natronolimnaea HS-1.

Int. J. Biol. Macromol. 51(4) , 618-26, (2012)

An acceptable strategy to incorporate canthaxanthin (CX) as a natural colorant into products is by means of oil-in-water emulsions. The used CX in this study was produced by bacterium Dietzia natronol...

Influence of canthaxanthin on broiler breeder reproduction, chick quality, and performance.

Poult. Sci. 90(7) , 1516-22, (2011)

To investigate the effect of canthaxanthin supplied via a maternal route on the production of both breeder hens and chickens, 270 Chinese Three-Yellow breeder hens were randomly divided into 2 groups ...

Determination of supplemental feeding needs for astaxanthin and canthaxanthin in salmonids by supramolecular solvent-based microextraction and liquid chromatography-UV/VIS spectroscopy.

Food Chem. 134(2) , 1244-9, (2012)

Development of simple and rapid analytical methods for predicting supplemental feeding requirements in aquaculture is a need to reduce production costs. In this article, a supramolecular solvent (SUPR...