| Canthaxanthin is a keto-carotenoid pigment widely distributed in nature. Carotenoids belong to a larger class of phytochemicals known as terpenoids. The chemical formula of canthaxanthin is C40H52O2. It was first isolated in edible mushrooms. It has also been found in green algae, bacteria, crustaceans, and bioaccumulates in fish such as carp, golden grey mullet, seabream and trush wrasse.
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 in feed for egg laying hens and 25 mg/kg in feed for other poultry and salmonids.
Canthaxanthin is a potent lipid-soluble antioxidant. The biological functions of canthaxanthin are related, at least in part, to its ability to function as an antioxidant (free radical scavenging/vitamin E sparing) in animal tissues. |
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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+ |
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| 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/C1=C(C)C(=O)CCC1(C)C |
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Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
biological pigment
An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
food colouring
A food additive that imparts colour to food. In European countries, E-numbers for permitted food colours are from E 100 to E 199, divided into yellows (E 100-109), oranges (E 110-119), reds (E 120-129), blues and violets (E 130-139), greens (E 140-149), browns and blacks (E 150-159), and others (E 160-199).
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food colouring
A food additive that imparts colour to food. In European countries, E-numbers for permitted food colours are from E 100 to E 199, divided into yellows (E 100-109), oranges (E 110-119), reds (E 120-129), blues and violets (E 130-139), greens (E 140-149), browns and blacks (E 150-159), and others (E 160-199).
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View more via ChEBI Ontology
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4,4'-dioxo-β-carotene
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ChemIDplus
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all-trans-β-carotene-4,4'-dione
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ChemIDplus
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canthaxanthin
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UniProt
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Canthaxanthin
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KEGG COMPOUND
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Carophyll Red
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ChemIDplus
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E 161g
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ChEBI
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Food Orange 8
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ChemIDplus
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Orobronze
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ChemIDplus
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1898520
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Reaxys Registry Number
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Reaxys
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514-78-3
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CAS Registry Number
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KEGG COMPOUND
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514-78-3
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CAS Registry Number
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ChemIDplus
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Suzuki K, Honjo H, Ichino N, Osakabe K, Sugimoto K, Yamada H, Kusuhara Y, Watarai R, Hamajima T, Hamajima N, Inoue T (2013)
Association of serum carotenoid levels with urinary albumin excretion in a general Japanese population: the Yakumo study.
Journal of epidemiology 23, 451-456 [PubMed:24097248]
[show Abstract]
BackgroundAlbuminuria is a risk factor for not only nephropathy progression but also cardiovascular disease. Oxidative stress may have a role in the positive association between albuminuria and cardiovascular disease.MethodsThis cross-sectional study investigated the associations of serum levels of carotenoids, which are dietary antioxidants, with albuminuria among 501 Japanese adults (198 men, mean age ± SD: 66.4 ± 10.0 years; 303 women, mean age ± SD: 65.4 ± 9.8 years) who attended a health examination. Serum levels of carotenoids were determined by high-performance liquid chromatography. Logistic regression analysis was used to estimate odds ratios (ORs) with 95% CIs for albuminuria after adjustment for age, body mass index, smoking habits, drinking habits, hypertension, diabetes mellitus, and dyslipidemia.ResultsPrevalence of albuminuria was 15.4% among men and 18.1% among women. Among women with albuminuria, geometric mean serum levels of canthaxanthin, lycopene, β-carotene, total carotenes, and provitamin A were significantly lower than those of normoalbuminuric women. Adjusted ORs for albuminuria among women in the highest tertiles of serum β-carotene (OR, 0.45; 95% CI, 0.20-0.98) and provitamin A (OR, 0.45; 95% CI, 0.20-0.97) were significantly lower as compared with those for women in the lowest tertile. There were no associations between serum carotenoids and albuminuria in men.ConclusionsAn increased level of serum provitamin A, especially serum β-carotene, was independently associated with lower risk of albuminuria among Japanese women. | Sujak A (2012)
Exceptional molecular organization of canthaxanthin in lipid membranes.
Acta biochimica Polonica 59, 31-33 [PubMed:22428120]
[show Abstract]
Canthaxanthin (β,β-carotene 4,4' dione) used widely as a drug or as a food and cosmetic colorant may have some undesirable effects on human health, caused mainly by the formation of crystals in the macula lutea membranes of the retina of an eye. Experiments show the exceptional molecular organization of canthaxanthin and a strong effect of this pigment on the physical properties of lipid membranes. The most striking difference between canthaxanthin and other macular pigments is that the effects of canthaxanthin at a molecular level are observed at much lower concentration of this pigment with respect to lipid (as low as 0.05 mol%). An analysis of the molecular interactions of canthaxanthin showed molecular mechanisms such as: strong van der Waals interactions between the canthaxanthin molecule and the acyl chains of lipids, restrictions to the segmental molecular motion of lipid molecules, modifications of the surface of the lipid membranes, effect on the membrane thermotropic properties and finally interactions based on the formation of the hydrogen bonds. Such interactions can lead to a destabilization of the membrane and loss of membrane compactness. In the case of the retinal vasculature, it can lead to an increase in the permeability of the retinal capillary walls and the development of retinopathy. | Goswami G, Chakraborty S, Chaudhuri S, Dutta D (2012)
Optimization of process parameters by response surface methodology and kinetic modeling for batch production of canthaxanthin by Dietzia maris NIT-D (accession number: HM151403).
Bioprocess and biosystems engineering 35, 1375-1388 [PubMed:22451081]
[show Abstract]
Dietzia maris NIT-D, a canthaxanthin producer, was isolated during routine screening of pigment-producing bacteria. Response surface methodology was applied for statistical designing of process parameters for biomass and canthaxanthin production. The effects of four process parameters (considered as independent variables), namely temperature (10-30 °C), pH (4.75-5.75), shaker speed (75-135 rpm) and percentage inoculum (0.5-2.5 %) on the biomass and canthaxanthin yield (considered as dependent variables) were studied. As much as 122 mg L(-1) of canthaxanthin was obtained when Dietzia maris NIT-D was incubated for 120 h at 25 °C and 120 rpm, initial pH and percentage inoculum being 5.5 and 2 % respectively. The pigment yield is the highest reported till date, with Dietzia maris as the test organism. The maximum biomass yield was 7.39 g L(-1) under optimized process parameters. The predicted values were also verified by validation experiments in 5-day fermentation. Different mathematical models were used to describe growth and production, considering the effect of glucose in batch mode. The kinetic constants were calculated by fitting the experimental data to the models. Cell growth was inhibited beyond a glucose concentration of 15 g L(-1). Andrews' model gave the best fit with a R (2) value of 0.9993. During the exponential growth phase, the specific growth rate was found to remain fairly constant with respect to time. There was no inhibitory effect due to intracellular product accumulation for all concentrations of glucose. This observation is the first of its kind, as previous studies have reported that increasing accumulation of intracellular carotenoid exerts greater degree of inhibition on growth. | Scaife MA, Ma CA, Armenta RE (2012)
Efficient extraction of canthaxanthin from Escherichia coli by a 2-step process with organic solvents.
Bioresource technology 111, 276-281 [PubMed:22353211]
[show Abstract]
Canthaxanthin has a substantial commercial market in aquaculture, poultry production, and cosmetic and nutraceutical industries. Commercial production is dominated by chemical synthesis; however, changing consumer demands fuel research into the development of biotechnology processes. Highly productive microbial systems to produce carotenoids can be limited by the efficiency of extraction methods. Extraction with hexane, acetone, methanol, 2-propanol, ethanol, 1-butanol, tetrahydrofuran and ethyl acetate was carried out with each solvent separately, and subsequently the most efficient solvents were tested in combination, both as mixtures and sequentially. Sequential application of methanol followed by acetone proved most efficient. Extraction efficiency remained stable over a solvent to biomass range of 100:1 to 55:1, but declined significantly at a ratio of 25:1. Application of this method to a canthaxanthin-producing Escherichia coli production system enabled efficient canthaxanthin extraction of up to 8.5 mg g(-1) dry biomass. | Kumar A, Srikanta AH, Peddha MS, Sukumaran UK, Govindaswamy V (2012)
A short-term toxicity study of Aspergillus carbonarius carotenoid.
International journal of toxicology 31, 158-165 [PubMed:22366116]
[show Abstract]
In a pharmacokinetic study, high-performance liquid chromatography analysis of blood samples of Wistar female rats fed with partially saturated canthaxanthin (PSC) of Aspergillus carbonarius showed the presence of the carotenoid in the plasma within 6 hours of feeding. In another study for safety assessment of PSC fed to rats over a period of 28 days at 0.05%, 0.10%, and 0.25%, the rats showed no changes in food intake. There were no significant differences observed in body weight, hematological parameters, or serum clinical enzymes compared to the control group not fed with PSC. Deposition of PSC in the eyes of the rats was also not observed. The results showed that PSC-fed rats were not adversely affected as far as toxicological studies were concerned. | Tanaka T, Shnimizu M, Moriwaki H (2012)
Cancer chemoprevention by carotenoids.
Molecules (Basel, Switzerland) 17, 3202-3242 [PubMed:22418926]
[show Abstract]
Carotenoids are natural fat-soluble pigments that provide bright coloration to plants and animals. Dietary intake of carotenoids is inversely associated with the risk of a variety of cancers in different tissues. Preclinical studies have shown that some carotenoids have potent antitumor effects both in vitro and in vivo, suggesting potential preventive and/or therapeutic roles for the compounds. Since chemoprevention is one of the most important strategies in the control of cancer development, molecular mechanism-based cancer chemoprevention using carotenoids seems to be an attractive approach. Various carotenoids, such as β-carotene, a-carotene, lycopene, lutein, zeaxanthin, β-cryptoxanthin, fucoxanthin, canthaxanthin and astaxanthin, have been proven to have anti-carcinogenic activity in several tissues, although high doses of β-carotene failed to exhibit chemopreventive activity in clinical trials. In this review, cancer prevention using carotenoids are reviewed and the possible mechanisms of action are described. | Rosa AP, Scher A, Sorbara JO, Boemo LS, Forgiarini J, Londero A (2012)
Effects of canthaxanthin on the productive and reproductive performance of broiler breeders.
Poultry science 91, 660-666 [PubMed:22334741]
[show Abstract]
The effects of supplementing canthaxanthin on productive and reproductive aspects of broiler breeders were examined in this study. In total, 360 female pullets and 36 roosters were placed in an open-sided house with 12 pens, each pen with an area of 7.0 m(2) (3.5 × 2.0 m). At 42 wk of age, the breeder hens and roosters were distributed into 2 experimental groups with similar BW and uniformity. From 46 to 66 wk of age, one group received 6 mg/kg of canthaxanthin supplemented in the diet and the other group received the diet without the addition of canthaxanthin (control diet). Body weight was measured every 28 d, the laying rate was calculated weekly, and mortality was evaluated at the end of the study. Twenty-one weekly incubations were performed to evaluate fertility and incubation responses. To evaluate the antioxidant effect of canthaxanthin at different storage times and during the incubation process, eggs from each treatment were subject to thiobarbituric reactive substances analysis. Body weight, mortality, and laying rate were not affected by the inclusion of canthaxanthin in the breeder's diets. An increase in hatchability of total and fertile eggs (P ≤ 0.0001 and P ≤ 0.0003, respectively) in breeders fed canthaxanthin during the experimental period was observed. Canthaxanthin also improved breeder fertility and reduced embryo mortality. This can be attributed to reductions in embryo mortality in the first 48 h of incubation and in the last wk of incubation. No differences were observed in BW and quality of the chicks. A reduction of thiobarbituric reactive substances was observed in yolks from stored hatching eggs produced by breeders fed diets plus canthaxanthin. The same effect was observed in yolks of eggs stored for 4 d and incubated for 7 d. The supplementation of broiler breeder diets with canthaxanthin improved the hatchability rate, fertility, and reduced the presence of thiobarbituric reactive substances in eggs. | He KH, Zou XL, Liu X, Zeng HY (2012)
[Determination of canthaxanthin and astaxanthin in egg yolks by reversed phase high performance liquid chromatography with diode array detection].
Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition 43, 113-117 [PubMed:22455145]
[show Abstract]
ObjectiveA method using reversed phase high performance liquid chromatography (RP-HPLC) coupled with diode array detector (DAD) was developed for the simultaneous determination of canthaxanthin and astaxanthin in egg yolks.MethodsSamples were extracted with acetonitrile in ultrasonic bath for 20 minutes and then purified by freezing-lipid filtration and solid phase extraction (SPE). After being vaporized to dryness by nitrogen blowing and made up to volume with methanol, the extract solution was chromatographically separated in C18 column with a unitary mobile phase consisting of acetonitrile. The proposed method was validated in terms of linearity, precision, accuracy, and limit of detection (LOD).ResultRegression analysis revealed a good linearity between peak area of each analyte and its concentration (r > or = 0.998). The intra- and inter-day relative standard deviations (RSDs) were less than 3.6% and 5.2%, respectively. LODs of canthaxanthin and astaxanthin were 0.035 and 0.027 microg/mL (S/N = 3). The average recoveries of canthaxanthin and astaxanthin were 91.5% and 88.7%.ConclusionThe proposed method is simple, fast and easy to apply. |
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