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14-September-2008 18:38:39 - Astaxanthin Astaxanthin IUPAC name 6S-6-Hydroxy-3-1E,3E,5E,7E,9E,11E,13E,15E,17E-18-4S-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 Identifiers CAS number 472-61-7 PubChem 5281224 SMILES CC1=CCCC@@HC1=OOCC\C=C\C =C\C=C\C=C\C=C\C=C/C\C=C\C=C /C\C=C\C2=CC=OC@HCC2CCOC\C\C Properties Molecular formula C40H52O4 Molar mass 596.84 g/mol Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references 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. 12 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 foods3a. The European Union actually European Commission considers it food dye within the E number system, E161j3b. Contents 1 Natural sources 2 Synthetic sources 3 Difference between Natural and Synthetic 4 Uses 4.1 For seafood and animals 4.2 For humans 5 The farm-raised salmon lawsuit 6 Astaxanthin in the food chain 7 Regulations 8 Trivia 9 References 10 External links Natural sources The following sources are being used for the commercial production of astaxanthin. Haematococcus pluvialis microalge 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. Amounts of Astaxanthin Found in Food Natural Astaxanthin Sources Astaxanthin Concentrationppm Salmonids Plankton Krill Arctic shrimp Phaffia Yeast Haematococcus pluvialis ~ 5 ~ 60 ~ 120 ~ 1200 ~ 8000 ~40,000 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 microalge6. It seems to accumulate the highest levels of astaxanthin in nature4a; 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 aquafeed.com points to some of the issues: Krill Krill 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. P. borealis P. borealis 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. Fuji Chemical Industry Japan Subsidiaries include: Astavita, BioReal, Inc. USA and Bioreal Sweden AB Formerly AstaReal AB and Fuji Health Science Inc., NJ, USA. Source: http://www.didgood.com/recipes/information/salmon/astaxanthin/astaxanthin.html Synthetic sources DSM Carophyll Pink 10% CWS formerly Hoffmann La Roche Carophyll Pink BASF Lucantin Pink The sources of synthetic astaxanthin are not available. It's definitely not in the literature, and the only information available is third-party. There are patents. There is one report of it being made from petrochemicals or petroleum. That said here is this: 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 Producers of Synthetic Astaxanthin Producers of Natural Astaxanthin Brand Name Producer Geographic Location Source AstaREAL Fuji Health Science Inc sub of Fuji USA Haematococcus pluvialis ECOTONE Acher Daniel Midland Illinois, USA Phaffia Rhodozyma Seeks Funding AlgaTech Israel Haematococcus pluvialis BioPrawns BioPrawns Norway Pandalus Borealis BioAstin Cyanotech Hawaii, USA Haematococcus pluvialis astaxanthin and Astafactor Mera Pharmaceuticals Hawaii, USA Haematococcus pluvialis - BioReal Inc. sub of Fuji Hawaii, USA Haematococcus pluvialis AstaCarox BioReal Sweden AB sub of Fuji Gustavsberg, Sweden Haematococcus pluvialis Parry's Natural Astaxanthin Parry Nutraceuticals Oonaiyur, India Haematococcus pluvialis Red-A Natural Astaxanthin Yunnan Green A Biological Project Co., LTD Yunnan, China Haematococcus pluvialis AQUASTA Tate and Lyle UK fermentation of carbohydrates dextrose - No website/Necton Portugal algae - No website/Sandypool Ltd. Ukraine krill Astazine Beijing Gingko Group Beijing, China Haematococcus pluvialis Brand Name Producer Geographic Location Source Carophyll Pink 10% CWS DSM - - Lucantin Pink BASF - - Formerly Carophyll Pink - certified by AFAQ 1993/1015 - in use since 198514 - product purchased from HR in 200315 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 production4b. 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.57 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 the relationship between astaxanthin and plumage - they admit this as well. More research is need, as proposed by all. Regulations FDA Title 21: Sec. 73.35 Astaxanthin FDA Title 21: Sec. 73.185 Haematococcus algae meal FDA 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 FOOD ADDITIVE STATUS LIST 2005 FDA ledger on applications for 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 roe at the Shiogama seafood market in Japan Salmon roe at the Shiogama seafood market in Japan 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 The references used in this article may be clearer with a different or consistent style of citation, footnoting, or external linking. 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 US patent application 20050014824 online here also EP patent 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=Retrievedb=pubmeddopt=Abstractlist_uids=12727382 6 http://microscope.mbl.edu/scripts/microscope.php?func=imgDetailimageID=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-b8bCcbcp0l0 17 http://www.nefsc.noaa.gov/sos/spsyn/iv/shrimp/ 18 http://www.israel21c.org/bin/en.jsp?enZone=HealthenDisplay=viewenPage=BlankPageenDispWhat=objectenDispWho=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 Astaxanthin - Frequently Asked Questions AstaFactor Technical Report Haematococcus Pluvialis and Astaxanthin Safety For Human Consumption Articles on Astaxanthin See reference table for a large well researched list of articles. aquafeed.com Natural Foods through marine Krill Meal - 09/09/2003 Development of microalgal pigments for aquaculture in Europe; Final Report, February, 2001. 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 1 The Effects of Three Carotenoid Sources on Growth and Pigmentation of Juvenile Freshwater Crayfish Cherax quadricarinatus Carophyll Pink 10% CWS - Astaxanthin for aquaculture, a DSM Product Astaxanthin for aquaculture - Carophyll Pink since 1985 v d e Carotenoids Carotenes: Carotene Alpha-carotene · Beta-carotene · Lycopene · Phytoene Phytofluene · Neurosporene Retinoids: Acitretin · Alitretinoin · Apocarotenal · Bexarotene · Etretinate · Fenretinide · Isotretinoin · Retinaldehyde · Tazarotene · Vitamin A Retinol, Tretinoin Xanthophylls: Antheraxanthin · Astaxanthin · Canthaxanthin · Citranaxanthin · Cryptoxanthin · Diadinoxanthin · Diatoxanthin · Dinoxanthin · Flavoxanthin · Fucoxanthin · Lutein · Neoxanthin · Rhodoxanthin · Rubixanthin · Violaxanthin · Zeaxanthin Other: Crocin · Crocetin · Peridinin · Food orange 7 Retrieved from http://en..org/wiki/Astaxanthin Categories: Food colorings | Pigments | CarotenoidsHidden category: references cleanup Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Esperanto Français Nederlands 日本語 SlovenÅ¡Ä?ina Svenska ä¸æ–‡ This page was last modified on 11 September 2008, at 23:31
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