Astaxanthin

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(6"S")-6-Hydroxy-3- [(1"E",3"E",5"E",7"E",9"E",11"E",13"E",15"E",17"E")-18- [(4"S")-4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl] -3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl] -2,4,4-trimethyl-1-cyclohex-2-enone

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Section1= Chembox Identifiers
CASNo=472-61-7
PubChem=5281224
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CC1=C(C(C [C@@H] (C1=O)O)(C)C)C=CC (=CC=CC(=CC=CC=C(/C)C=CC=C (/C)C=CC2=C(C(=O) [C@H] (CC2(C)C)O)C)C)C

Section2= Chembox Properties
Formula=C₄₀H₅₂O₄
MolarMass=596.84 g/mol
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Astaxanthin (pronounced as-tuh-zan'-thin) is a carotenoid. It belongs to a larger class of phytochemicals known as terpenes. It is classified as a xanthophyll, which means "yellow leaves". Like many carotenoids, it is a colorful, fat/oil-soluble pigment. Astaxanthin can be found in microalgae, yeast, salmon, trout, krill, shrimp, crayfish, crustaceans, and the feathers of some birds. [1] [2] Professor Basil Weedon was the first to map the structures of astaxanthin.

Astaxanthin, unlike some carotenoids, does not convert to Vitamin A (retinol) in the human body. Too much Vitamin A is toxic for a human, but astaxanthin is not. However, it is a powerful antioxidant; it is 10 times more capable than other carotenoids. [3]

While astaxanthin is a natural nutritional component, it can be found as a food supplement. The supplement is intended for human, animal, and aquaculture consumption. The commercial production of astaxanthin comes from both natural and synthetic sources.

The FDA approved astaxanthin (See: Regulations below) as a food coloring (or color additive) for specific uses in animal and fish foods [3a] . The European Union (actually European Commission) considers it food dye within the E number system, E161j [3b] .

Natural sources

The following sources are being used for the commercial production of astaxanthin.
* [http://microscope.mbl.edu/scripts/microscope.php?func=imgDetail&imageID=8688 Haematococcus pluvialis] (microalge)
* [http://www.microbelibrary.org/ASMOnly/details.asp?id=1971&Lang= Xanthophyllomyces dendrorhous] , formerly Phaffia rhodozyma (yeast)
* Euphausia pacifica (Pacific krill)
* Euphausia superba (Antarctic krill)
* Pandalus borealis (shrimp)

As a natural source, the following can be found in nature (or a production facility) with the approximate concentrations listed.

Source: http://algatech.com/astax.htm

With that, each source has its own production issues.

Currently, the primary natural source for astaxanthin is "haematococcus pluvialis" (microalge) [6] . It seems to accumulate the highest levels of astaxanthin in nature [4a] ; commercially more than 40 g of astaxanthin per kilo of dry biomass. [4] It has the advantage of the population doubling every week, which means scaling up is not an issue; simply open another plant. However, it does require some expertise among the personnel and that might be its downfall.

For "Xanthophyllomyces dendrorhous" (yeast), interestingly enough it has similar advantages, but requires refrigeration once harvested (above freezing, <6 degrees Celsius/43 degrees Fahrenheit). It also has the problem of being low in nutritional value, unlike krill or shrimp. Since it is not ocean-based, it has the issue of not carrying those ocean-like traits. Since its chief advantage is price, it will certainly be available for the cost-conscious consumer.

For "Euphausia superba" (krill), this report from [http://www.aquafeed.com/article.php?id=365 aquafeed.com] points to some of the issues:

The Krill fishing operation is complex. It is done in Antarctic waters, under extreme weather conditions and far away from ports with substantial operational complexities. Krill's fishing location and the difficult weather conditions in the main fishing area, together with the costs involved in the operation, have contributed to a slow development of the industry. Krill fishing is by far different to any other fishing operation today known. The knowledge to work with it belongs to very few people in the world.

Nonetheless as the article points out, producers still venture out. They include the Japanese, the Polish, the Russians, and Ukrainians. Lastly, krill will always have environmental issues, but being lower on the food chain allows it to reproduce more, and faster than larger ocean creatures—at least we hope.

"Pandalus Borealis" (shrimp) might be seen as "shrimp meat" from the grocery store, or in a shrimp cocktail, or shrimp salad. Nutritious, tasty, and in danger of overfishing. [17] Nonetheless, just the head and shell are used. That leads to this source having limitations one way or another.

* Formerly Carophyll Pink - certified by AFAQ (1993/1015) - in use since 1985 [14] - product purchased from HR in 2003 [15]

Source: http://www.didgood.com/recipes/information/salmon/astaxanthin/astaxanthin.html

Difference between Natural and Synthetic

Astaxanthin has two chiral centers, at the 3 and 3' positions. Therefore, there are three stereoisomers; (3-R,3'-R), (3-R,3'-S) (meso), and (3-S,3'-S). Synthetic astaxanthin contains a mixture of the three, in approximately 1:2:1 proportions. Naturally occurring astaxanthin varies considerably from one organism to another. The astaxanthin in fish is of whatever stereoisomer the fish ingested. [3c]

Uses

In 1948, Nobel prizewinner George Wald surmized, "This could lead to an important new use of astaxanthin as a drug delivery for medicines that are insoluble in water, and give designers of new food colourants or dyestuffs an interesting new capability." [19]

Astaxanthin is used as a feed supplement for salmon, crabs, shrimp, chickens and egg production [4b] . Regardless of the source, astaxanthin provides some important benefits beyond coloration. It also has been found to be essential for proper growth and survival. [4]

For seafood and animals

The primary use of synthetic astaxanthin today is as an animal feed additive to impart coloration, this includes farm-raised salmon and egg yolks. [4] In that, synthetic carotenoid (i.e., coloured yellow, red or orange) pigments represent about 15-25% of the cost of production of commercial salmon feed. [4c] Today, essentially all commercial astaxanthin for aquaculture is produced synthetically from petrochemical sources, with an annual turnover of over $200 million, and a selling price of ~$2000 per kilo of pure astaxanthin. [4]

For humans

Currently, the primary use for humans is as a food supplement. Research shows that due to astaxanthin's potent antioxidant activity, it may be beneficial in cardiovascular, immune, inflammatory and neurodegenerative diseases. [9] Research supports the assumption that it protects body tissues from oxidative damage. [5] [7] It also crosses the blood-brain barrier, which makes it available to the eye, brain and central nervous system to alleviate oxidative stress that contributes to ocular, and neurodegenerative diseases such as glaucoma and Alzheimer's. [8]

The farm-raised salmon lawsuit

The class action lawsuits were filed against some major grocery store chains for not clearly labeling the salmon "color added". [23] The chains follow up quickly by labeling all such salmon as "color added". "However, Smith & Lowney persisted with the suit for damages, but a Seattle judge dismissed (...)(the case) , ruling that enforcement of the applicable food laws was up to government and not individuals." [24]

Astaxanthin in the food chain

It's been speculated that gulls are "flushed" pink when molting, especially in areas with farm-raised salmon. [20] To say the least, this is intriguing. However, those speculating quite readily admit they don't know why. Even so, the bottom line is that not enough is known about [http://www.didgood.com/recipes/information/salmon/astaxanthin/research-Bird-Plumage/pdf.html the relationship between astaxanthin and plumage] - they admit this as well.

More research is need, as proposed by all.

Regulations

FDA [http://www.cfsan.fda.gov/~lrd/cfr73-35.html Title 21: Sec. 73.35 Astaxanthin]

FDA [http://www.cfsan.fda.gov/~lrd/cfr73185.html Title 21: Sec. 73.185 Haematococcus algae meal]

FDA [http://www.cfsan.fda.gov/~dms/opa-col2.html Note 1.]
The color additives Astaxanthin, Ultramarine blue, Canthaxanthin, Synthetic iron oxide, Dried algae meal, Tagetes (Aztec marigold) meal and extract, and Corn endosperm oil are approved for specific uses in animal foods (see 21 CFR 73.35,73.50, 73.75, 73.200, 73.275, 73.295, 73.315, respectively). Haematococcus algae meal (21 CFR 73.185) and Phaffia yeast (21 CFR 73.355) for use in fish feed to color salmoids were added in 7/6/2000.

[pdf] [http://www.cfsan.fda.gov/~acrobat/opa-appa.pdf FOOD ADDITIVE STATUS LIST] 2005

FDA ledger on applications for
[http://www.cfsan.fda.gov/~dms/ds-ingrd.html New Dietary Ingredients in Dietary Supplements] 1999-2001

Trivia

*There are over 600 known carotenoids. 100 different carotenoids are generally encountered in foods. [1] About half of the roughly 50 carotenoids in the human diet are absorbed into the blood stream. [1a] .

*Astaxanthin has 100-500 times the antioxidant capacity of Vitamin E and 10 times the antioxidant capacity of beta-carotene. Many laboratory studies also indicate astaxanthin is a stronger antioxidant than lutein, lycopene and tocotrienols. [8]

*Only two (2) companies world-wide synthesize Astaxanthin. [16]

*Synthetic astaxanthin fetches $2000 a kilogram on the market, while the natural product is sold for over $7000 a kilo. [18]

*Salmon roes contain astaxanthin that gives them their reddish color and protects them from ultraviolet.

*It is believed that algae will expose its astaxanthin when the sun hits it, to protect itself.

*Flamingos can't make use of astaxanthin, so it goes to their feathers.

*Lobsters, shrimp, and some crabs turn red when cooked because the astaxanthin, which was bound to the protein, unwinds. [21]

*Cardinals seem to produce astaxanthin from carotenoids when molting, even when fed primarily seed with natural yellow dye. [22]

*While it constitutes a tiny portion of salmon feed (50 to 100 parts per million), astaxanthin represents a major share of the cost, up to 20 percent. [23]

References

Note: Must align numbers.

* [1] http://www.herbalchem.net/Carotenoids_Introductory.htm
* [1a] http://www.benbest.com/nutrceut/phytochemicals.html#carotenoids
* [2] http://www.herbalchem.net/Carotenoids_Intermediate.htm - See: Astaxanthin
* [3] http://www.benbest.com/nutrceut/phytochemicals.html#astaxanthin
* [3a] http://www.cfsan.fda.gov/~dms/opa-col2.html - See Note 1.
* [3b] http://www.food-info.net/uk/e/e100-200.htm - Currently unlisted. Will look for a better ref.
* [3c] cite patent|US|20050014824|application ( [http://www.patentdebate.com/PATAPP/20050014824 online here] ) (also cite patent|EP|1442083)
* [4] http://algatech.com/astax.htm
* [4a] http://www.astafactor.com/algae.htm
* [4b] http://www.astaxanthin.org/wellness.htm - just the egg part
* [4c] http://www.pac.dfo-mpo.gc.ca/aquaculture/topics/colour_e.htm
* [5] http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=12727382
* [6] http://microscope.mbl.edu/scripts/microscope.php?func=imgDetail&imageID=8688 - Haematococcus pluvialis
* [7] http://www.cyanotech.com/pdfs/bioastin/batl09.pdf
* [8] http://www.beta-glucan-info.com/astaxanthin-questions-answers.htm
* [9] http://www.didgood.com/recipes/information/salmon/astaxanthin/resources/NutrientReview.search.html
* [10] http://www.aquafeed.com/article.php?id=365
* [11] http://ift.confex.com/ift/2002/techprogram/paper_12592.htm
* [12] http://www.bioprawns.no/product.html
* [13] http://www.certifiedorganic.bc.ca/rcbtoa/services/aquaculture-standards.html
* [14] http://www.dsm.com/en_US/downloads/dnp/51643_aqua.pdf
* [15] http://www.dsm.com/en_US/html/dnp/about_history.htm
* [16] http://www.corporate.basf.com/en/innovationen/labors/wirk_effektstoffe/wirk_effekt/astaxanthin.htm?id=V00-3Y-b*8bCcbcp0l0
* [17] http://www.nefsc.noaa.gov/sos/spsyn/iv/shrimp/
* [18] http://www.israel21c.org/bin/en.jsp?enZone=Health&enDisplay=view&enPage=BlankPage&enDispWhat=object&enDispWho=Articles%5El986
* [19] http://www.guardian.co.uk/uk_news/story/0,3604,765263,00.html
* [20] http://www.public.asu.edu/~kjmcgraw/pubs/JFO2006.pdf
* [21] http://www.ochef.com/718.htm
* [22] http://www.colorado.edu/chemistry/chem5181/HP_GCMS_Paper2.pdf
* [23] http://www.smithandlowney.com/salmon/
* [24] http://www.seafoodmonitor.com/sample/salmon.html

External links

* [http://www.beta-glucan-info.com/astaxanthin-questions-answers.htm Astaxanthin - Frequently Asked Questions]
* AstaFactor Technical Report [http://www.astafactor.com/techreports/tr3005-001.htm Haematococcus Pluvialis and Astaxanthin Safety For Human Consumption]
* [http://www.algatech.com/astax2.htm Articles on Astaxanthin] See reference table for a large well researched list of articles.
* aquafeed.com [http://www.aquafeed.com/article.php?id=439 Natural Foods through marine Krill Meal ] - 09/09/2003
* [http://www.biomatnet.org/secure/Fair/R1518.htm Development of microalgal pigments for aquaculture] in Europe; Final Report, February, 2001.
* [http://www.scielo.cl/scielo.php?pid=S0716-97602004000100009&script=sci_arttext Study of the expression of carotenoid biosynthesis genes in wild-type and deregulated strains of Xanthophyllomyces dendrorhous (Ex.: Phaffia rhodozyma).]
* Multibudding in Xanthophyllomyces dendrorhous Cells Under Hydric and Nitrogen Stress [http://www.microbelibrary.org/ASMOnly/details.asp?id=1971]
* [http://www.agri.gov.il/AnimalScience/Aquaculture/Rep-Harpaz2.html The Effects of Three Carotenoid Sources on Growth and Pigmentation of Juvenile Freshwater Crayfish Cherax quadricarinatus]
* [http://www.dsm.com/en_US/downloads/dnp/51640_aqua.pdf Carophyll Pink 10% CWS] - Astaxanthin for aquaculture, a DSM Product
* [http://www.dsm.com/en_US/html/dnpus/an_carot_caro_pink1985.htm Astaxanthin for aquaculture] - Carophyll Pink since 1985