Canthaxanthin
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Canthaxanthin is a keto-carotenoid pigment widely distributed in nature.
Carotenoids Carotenoids (), also called tetraterpenoids, are yellow, orange, and red organic pigments that are produced by plants and algae, as well as several bacteria, and fungi. Carotenoids give the characteristic color to pumpkins, carrots, parsnips, co ...
belong to a larger class of phytochemicals known as
terpenoid The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes" ...
s. The chemical formula of canthaxanthin is C40H52O2.Opinion on the use of canthaxanthin in feedingstuffs for salmon ...
/ref> It was first isolated in edible mushrooms. It has also been found in
green alga The green algae (singular: green alga) are a group consisting of the Prasinodermophyta and its unnamed sister which contains the Chlorophyta and Charophyta/Streptophyta. The land plants (Embryophytes) have emerged deep in the Charophyte alga as ...
e,
bacteria Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one Cell (biology), biological cell. They constitute a large domain (biology), domain of prokaryotic microorganisms. Typically a few micrometr ...
,
crustacean Crustaceans (Crustacea, ) form a large, diverse arthropod taxon which includes such animals as decapods, seed shrimp, branchiopods, fish lice, krill, remipedes, isopods, barnacles, copepods, amphipods and mantis shrimp. The crustacean group can ...
s, and
bioaccumulate Bioaccumulation is the gradual accumulation of substances, such as pesticides or other chemicals, in an organism. Bioaccumulation occurs when an organism absorbs a substance at a rate faster than that at which the substance is lost or eliminated ...
s in fish such as carp,
golden grey mullet The golden grey mullet (''Chelon aurata'') is a fish in the family Mugilidae. Description It has hydrodynamic, very elegant elongated, more or less cylindrical body, with strong tail-fin. It has dark gray back that transit into silver white towa ...
,
seabream The Sparidae are a family of fish in the order Perciformes, commonly called sea breams and porgies. The sheepshead, scup, and red seabream are species in this family. Most sparids are deep-bodied compressed fish with a small mouth separated by ...
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 Trout are species of freshwater fish belonging to the genera '' Oncorhynchus'', '' Salmo'' and '' Salvelinus'', all of the subfamily Salmoninae of the family Salmonidae. The word ''trout'' is also used as part of the name of some non-salm ...
feed, salmon feed and poultry feed. The
European Union The European Union (EU) is a supranational political and economic union of member states that are located primarily in Europe. The union has a total area of and an estimated total population of about 447million. The EU has often been de ...
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.


Biosynthesis

Due to the commercial value of carotenoids, their biosynthesis has been studied extensively in both natural producers, and non-natural (heterologous) systems such as the bacteria ''Escherichia coli'' and yeast ''Saccharomyces cerevisiae''. Canthanaxanthin biosynthesis proceeds from beta-carotene via the action of a single protein, known as a beta-carotene ketolase, that is able to add a
carbonyl In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containi ...
group to carbon 4 and 4' of the beta carotene molecule. Although functionally identical, several distinct beta-carotene ketolase proteins are known. That is to say they differ from an evolutionary perspective in their primary amino acid/protein sequence. They are different proteins that complete the same function. Thus, bacterial (CrtW) and micro-algal beta-carotene ketolase proteins such as ''BKT'' isolated from ''
Haematococcus pluvialis ''Haematococcus pluvialis'' is a freshwater species of Chlorophyta from the family Haematococcaceae. This species is well known for its high content of the strong antioxidant astaxanthin, which is important in aquaculture, and cosmetics. The hig ...
'' are known. Due to the nature of canthaxanthin, relative to
astaxanthin Astaxanthin is a keto- carotenoid within a group of chemical compounds known as terpenes. Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups. It is a lipid-soluble pigment with r ...
(a carotenoid of significant commercial value) these beta-carotene ketolase proteins have been studied extensively. An ''E. coli'' based production system has been developed, that achieved canthanaxanthin production at 170 mg/L in lab scale fermentation.


Presence in fish

Canthaxanthin is not found in wild Atlantic Salmon, but is a minor carotenoid in
Pacific Salmon ''Oncorhynchus'' is a genus of fish in the family Salmonidae; it contains the Pacific salmon and Pacific trout. The name of the genus is derived from the Greek ὄγκος (ónkos, “lump, bend”) + ῥύγχος (rhúnkhos, “snout”), i ...
. Canthaxanthin is used in farm-raised trout. Canthaxanthin is used in combination with
astaxanthin Astaxanthin is a keto- carotenoid within a group of chemical compounds known as terpenes. Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups. It is a lipid-soluble pigment with r ...
for some salmon feeds.


Presence in birds

The antioxidant characteristics of canthaxanthin have been studied by a number of authors and experiments have shown that the presence of canthaxanthin can potentially help to reduce oxidation in a number of tissues including broiler meat and the chick embryo. In the egg, canthaxanthin is transferred from yolk to the developing embryo where it might help to protect the developing bird against oxidative damage, particularly during the sensitive periods of hatching and early posthatch life.


Effects on human pigmentation and health

When ingested for the purpose of simulating a tan, its deposition in the
panniculus Panniculus, often incorrectly referred to as pannus, is a medical term describing a dense layer of fatty tissue, consisting of excess subcutaneous fat within the lower abdominal region. Panniculi can form after rapid weight loss, as seen with st ...
imparts a golden orange hue to the skin.James, William; Berger, Timothy; Elston, Dirk (2005). ''Andrews' Diseases of the Skin: Clinical Dermatology''. (10th ed.). Saunders. . In the late 1980s, the safety of canthaxanthin as a feed and a food additive was drawn into question as a result of a completely un-related use of the same carotenoid. A reversible deposition of canthaxanthin crystals was discovered in the retina of a limited number of people who had consumed very high amounts of canthaxanthin via sun- tanning pills – after stopping the pills, the deposits disappeared and the health of those people affected was fully recovered. However, the level of canthaxanthin intake in the affected individuals was many times greater than that which could ever be consumed via poultry products - to reach a similar intake, an individual would have to consume more than 50 eggs per day, produced by hens fed practical levels of canthaxanthin in their diets. Moreover, it was demonstrated by Hueber et al. that ingestions of canthaxanthin cause no long-term adverse effects, and that the phenomenon of crystal deposition on the retina is reversible and does not result in morphological changes. Although this incidence was totally unrelated and very different from the feed or food use of canthaxanthin, as a link had been drawn between canthaxanthin and human health, it was important that the use of canthaxanthin as a feed and food additive should be reviewed in detail by the relevant authorities, both in the EU and at an international level. The first stage of this review process was completed in 1995 with the publication by
Joint FAO/WHO Expert Committee on Food Additives The Joint FAO/WHO Expert Committee on Food Additives (JECFA) is an international scientific expert committee that is administered jointly by the Food and Agriculture Organization of the United Nations (FAO) and the World Health Organization (WHO). ...
(JECFA) of an Acceptable Daily Intake (ADI) for canthaxanthin of 0.03 mg/kg bodyweight. The work of JECFA was subsequently reviewed and accepted within the EU by the SCF (EU Scientific Committee for Food) in 1997. The conclusion of both these committees was that canthaxanthin is safe for humans. Recently (2010), the EFSA Panel on Food Additives and Nutrient sources added to food (ANS) published a revised version of the safety assessment of Canthaxanthin, reconfirming the already set ADI. The
Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respon ...
(FDA) has no "tanning pills" approved for sale in the United States. In spite of this, there are companies that continue to market such products, some of which contain canthaxanthin. The FDA considers such items "adulterated cosmetics" and as a result sent warning letters to the firms citing such products as containing "a color additive that is unsafe within the meaning of section 721(a) of the FD&C Act (FD&C Act, sec. 601(e))." According to the FDA, :


References

{{Carotenoids Food colorings Carotenoids Cosmetics chemicals Disturbances of human pigmentation Tetraterpenes Cyclohexenes E-number additives