2ri2017
Astaxanthin
From Wikipedia, the free encyclopedia
Astaxanthin /esto'2en9ny is a keto-carorenoid. "4151 Jt
belongs to a larger class of chemical compounds known as
terpenes (in Asthaxanthin's case, a tetraterpenoid); terpen:
are built from five carbon precursors: isopenteny! diphosphate
(or IPP) and dimethylally! diphosphate (or DMAPP).
Astaxanthin is classified as a xanthophyll (originally derived
from a word meaning "ycllow leaves" since yellow plant leat
pigments were the first recognized of the xanthophyll family
of carotenoids), but currently employed to describe
carotenoid compounds that have oxygen-containing moities,
hydroxyl (OH) or ketone (C=O), such as zeaxanthin and
canthaxanthin, Indeed, astaxanthin is a metabolite of
zeaxanthin and/or canthaxanthin, containing both hydroxyl
and ketone functional groups. Like many carotenoids,
astaxanthin is a colorful, lipid-soluble pigment. This colour is
due to the extended chain of conjugated (alternating double
and single) double bonds at the centre of the compound, This,
chain of conjugated double bonds is also responsible for the
antioxidant function of astaxanthin (as well as other
carotenoids) as it results in a region of decentralized electrons
that can be donated to reduce a reactive oxidizing molecule.
Astaxanthin is found in microalgae, yeast, salmon, trout, krill,
shrimp, crayfish, crustaceans, and the feathers of some birds.
It provides the red color of salmon meat and the red color of
cooked shellfish. Professor Basil Weedon's group was the first
to prove the structure of astaxanthin by synthesis, in 1975.{9]
Astaxanthin, unlike several carotenes and one other known,
carotenoid, is not converted to vitamin A (retinol) in the
human body. Like other carotenoids, astaxanthin has self
limited absorption orally and such low toxicity by mouth that
no toxic syndrome is known, It is an antioxidant with a
slightly lower antioxidant activity in some model systems
than other carotenoids. However, in living organisms the free~
radical terminating effectiveness of each carotenoid is heavily
modified by its lipid solubility, and thus varies with the type
of system being protected.(7]
While astaxanthin is a natural dietary component, it can also
be used as a food supplement. The supplement is intended for
human, animal, and aquaculture consumption. The industrial
production of astaxanthin comes from both natural and
synthetic sources.
iteev/enwikipedia.craNwiki“Astexerthin
Astaxanthin Wikipedia
Astaxant
Names
TUPAC name
(65)-6-Hydroxy-3-
[(1E,3E,5E,7E,9E, 11E, 13E,1SE,17B)-18-[(45)-4-
hydroxy
cyclohexenyl]-3,7, 12, 16-tetramethyloctadeca-
1,3,5,7,9,11,13,15, 1 7nonaenyl]-2,4.4
cyclohex
6,6-trimethyl-3-ox0-1+
‘imethyl-
(Other names
3,3'-dihydroy-fecarotene-4,4'-dione; Astaxanthin
(6CD; B-Carotene-4,4'-dione, 3,3'-dihydrony-, alle
trans- (BCI); (38,3'S)-Astaxanthin; (3,3'S)-
Astaxanthin; (38,3°S)-all-trans-A staxanthin; (S,8)-
n; Aquasta; AstaREAL; AstaXin;
Astured; Astaxanthin, all-trans; Astots 100; Astots
50: BioAstin; BioAstin oleoresin; Carophyll Pink;
Lucantin Pink; NatuRose; Natupink; Ovoester; alle
Astaxant
trans-Astaxanthin; trans-Astaxanthin |!
Identifiers
(CAS Number 1472-61-17 (htip://www.commonch
cemiistry.org/ChemicalDetail. aspx?
ref=472-61-7)%
3D model (Imol) [Interactive image (httpi//chemanp
s.stolaf.edu/jmolimol.php?model
=O%ADCISCO%2BMIDCKZ
8%5CC%IDC%SCCH2BYID
(C%SCO%IDOXSCC%28"ID
CC%IDCASCCHIDC%MZ
oSCC%IDC%SCORIDCEMWZ
8%SCC%IDC%SCCL%IDC%2
le
18amie Astaxanthin Wikipedia
The U.S. Food and Drug, Administration (FDA) has approved
astaxanthin as a food coloring (or color additive) for specific
uses in animal and fish foods./*! The European Commission
considers it food dye and it is given the E number E161}.P)
‘Natural astaxanthin is generally recognized as safe (GRAS)
by the FDA,°ll!] put as a food coloring in the United States
it is restricted to use in animal food.!2)
Contents
Natural sources
Synthetic sources
Metabolic engineering
Difference between natural and synthetic forms
Uses
# 5.1 For seafood and animals
= 5.2 For humans
Role in the food chain
Regulations
References
External links
uae
wnus
Natural sources
Astaxanthin is present in most red-coloured aquatic
organisins, The content varies from species to species, but
also from individual to individual as it is highly dependent on
diet and living conditions, Astaxanthin, and other chemically
related asta-carotenoids, has also been found in 2 number of
lichen species of the arctic zone.
The primary natural sources for commercial production of
astaxanthin comprise the following:
Euphausia pacifica (Pacific keill)
Euphausia superba (Antarctic krill)
Haematococcus pluvialis (MicroAlgae){4)
Pandalus borealis (Arctic shrimp)
Xanthophyllomyces dendrorhous, formerly Phaffia
rhodozyma (yeast)
Astaxanthin concentrations in natural sources as found in
nature are approximately:
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SCC%28%3D0%29%SBO%d
(0%40H%SD%280%29CC1%28
1€%29€%29C%29C%29C%29
(€%29C%29C%28C%29%28C%
290% SBC%A0%40%SD20%2
9c)
(ChEBI
(CHEBI:40968 (htps://www.ebi.a
c.ukichebiisearchld.do?chebild~4
(0968) *
(ChEMBL
(ChEMBL44575 | (hetpsiliwww.c
bi.ac.uk/chembldb/index.php/com|
pound/inspect/ChEMBL445751)
x
(ChemSpider
14444636 (http://www.chemspide
+.com/Chemical-Structure.44446
36.heml) “
ECHA InfoCard
100.006.776 (htips://echa.europa.
ew/substance-information/-/subssta,
‘nceinfo/ 100.006.776)
E number E161; (colours)
PubChem 5281224 (htps://pubchem.nebi.nl
im.nih. gov/compound/5281224)
UNI 8XPW32PR7I (http:/dusis.alm.
nih. gov/sts/srsdirect,jsp?regno-8
XPW32PRI1) ¢
InChi
SMILES,
Properties
(Chemical formule |CypHs204
Molar mass 596.84 g/mol
‘Appearance red solid powder
Density 1.071 gmt 2)
[Melting point 216 °C (421 °F; 489 Ky)
Boiling point
74 °C (1,425 °F; 1,047 KP
Solubility
30 gil in DCM; 10 g/L im
CHCly; 0.5 g/L in DMSO; 0.2
g/L in acetone 1
Except where otherwise noted, data are given for
materials in their standard state (at 25 °C [77 °F],
100 kPa),
282ri201T Astaxanthin Wikipedia
se Astaxanthin concentration Infobox references
jource
(ppm)
Salmonids ~ 5
Plankton ~ 60
krill ~ 120
Arctic shrimp (P Ber
borealis)
Phaffia yeast ~ 10,000
Haemaroc coccus pare)
pluvialis ‘The shell and smaller parts of the
bodily tissue of Pandalus borealis
Algae are the primary natural source of astaxanthin in the aquatic food (Atetie shrimp) is colored by
chain, Currently, the primary industrial source for natural astaxanthin is the gaxanhin, and is used commercially
microalgae Hacmatococcus pluvialis. Haematococcus pluvialis seems to totais ilabenilitn tole
accumulate the highest levels of astaxanthin in nature. Commercially. more
than 40 g of astaxanthin can be obtained from one kg of dry biomass.!"3)
Haematococeus pluviatis has the advantage of the population doubling
every week, which means scaling up is not an issue. However, it does
require some expertise to grow the algae with a high astaxanthin content,
Specifically, the microalgae are grown in two phases. First, in the green
phase, the cells are given an abundance of nutrients to promote
proliferation of the cells. In the subsequent red phase, the cells are deprived
of nutrients and subjected to intense sunlight to induce encystment
(carotogenesis), during which the cells produce high levels of astaxanthin
as a protective mechanism against the environmental stress, The cells, with,
their high concentrations of astaxanthin, are then harvested 141 A Haematococeus phavialis cyst fi
with astaxanthin (red),
Phafiia yeast Yanthophyllomyces dendrorhous exhibits 100% free, non-
esterified astaxanthin, which is considered advantageous because it is
readily absorbable and need not be hydrolysed in the digestive tract of the
fish. In contrast to synthetic and bacteria sources of astaxanthin, yeast
sources of astaxanthin consist mainly of the (32, 3°R)-form, an important
astaxanthin source in nature, Finally, the geometrical isomer, all-E, is
higher in yeast sources of astaxanthin, as compared to synthetic sources.
This contributes to greater efficacy because the all-E (trans) isomer has
greater bio-availability than the ciy isomer.)
In shellfish, astaxanthin is almost exclusively concentrated in the shells, Krill is also used as an astaxanthin
with only low amounts in the flesh itself, and most of it only becomes source
visible during cooking, as the pigment separates from the denatured
proteins that otherwise binds it. For obtaining astaxanthin from Euphausia
superba (Antarctic krill), there are a number of issues:(!6)
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
iteev/enwikipedia.craNwiki“Astexerthin 382ri2017 Astaxanthin Wikipedia
operation, have contributed to a slow development of the industry. Krill fishing is by far different than
any other fishing operation today known. The knowledge to work with it belongs to very few people
in the world.
Astaxanthin is also commercially collected fiom shrimp processing waste. 12,000 pounds of wet shrimp shells can
yield a 6-8 gallon astaxanthin/triglyceride oil mixture_!"7)
Synthetic sources
Nearly all commercial astaxanthin for aquaculture is produced synthetically, with an annual turnover of over $200
million and a selling price of roughly $5000-6000 per kilo as of July 2012.3] However, synthetic production of
astaxanthin is not preferred in some cases because synthetic astaxanthin contains a mixture of stereoisomers.
Astaxanthin is fairly abundant and obtainable from narural sources, and some consumers prefer natural products
over synthetic ones.l"41
An efficient synthesis from isophorone, cis-3-methyl-2-penten-4-yn-1-ol and a symmetrical Cg-dialdehyde has
been discovered and is used commercially. It combines these chemicals together with an ethynylation and then a
Wittig reaction.!!®] Two equivalents of the proper ylide combined with the proper dialdehyde in a solvent of
staxanthin in up to 88% yields!)
°. KN
2 ~ PPh + mhw~
methanol, ethanol, or a mixture of the two, yields a
Br
Ho’
7 aa Saye eS 0
Ho"
Synthesis of astaxanthin by Wittig reaction
Metabolic engineering
The cost of astaxanthin production, high commercial price and lack of a leading fermentation production systems,
combined with the shortfalls of chemical synthesis mean that research into alternative fermentation production
methods has been carried out. Metabolic engineering offers the opportunity to create biological systems for the
production of a specific target compound. The metabolic engineering of bacteria (Escherichia coli) recently
allowed production of astaxanthin at >90% of the total carotenoids, providing the first engineered production
system capable of efficient astaxanthin production! Astaxanthin biosynthesis proceeds from beta-carotene via
either zeaxanthin or canthaxanthin. Historically, it has been assumed that astaxanthin biosynthesis proceeds along
both routes. However, recent work has suggested that efficient biosynthesis may, in fact, proceed from beta-
carotene to astaxanthin via zeaxanthin.24I72] The production of astaxanthin by metabolic engineering, in isolation,
will not provide a suitable altemative to current commercial methods. Rather, a bioprocess approach should be
adopted. Such an approach would consider fermentation conditions and economics, as well as downstream,
processing (extraction). Carotenoid extraction has been studied extensively, for example, the extraction of
iteev/enwikipedia.craNwiki“Astexerthin 432ri2017 Astaxanthin Wikipedia:
canthaxanthin (a precursor to astaxanthin) was studied within an £, coli production process demonstrating that
extraction efficiency was increased substantially when two solvents, acetone and methanol, were used sequentially
rather than as a combined solution.29)
Difference between natural and synthetic forms
Astaxanthin has two chiral centers, at the 3- and 3'-positions. Therefore, there are three stereoisomers; (3R,3'R),
(32,3'5) (meso), and (35.3'5). 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.|"4] The astaxanthin produced by Haematococeus pluvialis, which
is commonly used in the feed of animals that are in turn consumed by humans, is the (35,3’S) stereoisomer!!4]
Uses
Astaxanthin is used as a feed supplement for salmon, crabs, shrimp, chickens and egg production.25)
For seafood and animals
The primary use of synthetic astaxanthin today is as an animal feed additive to impart coloration, including farm-
raised salmon and egg yolks.l'3] Synthetic carotenoid pigments colored yellow, red or orange represent about 15—
25% of the cost of production of commercial salmon feed.!5! Today, almost all commercial astaxanthin for
aquaculture is produced synthetically from petrochemical sources.(27) 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%.)
Class action lawsuits have been filed against some major grocery store chains for not clearly labeling the salmon
"color added") The chains followed up quickly by labeling all such salmon as “color added". "....aw-firm 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,"
For humans
The primary use for humans is as a dietary supplement. Research suggests that, due to astaxanthin's antioxidant
activity, it may be beneficial in cardiovascular, immune, inflammatory and neurodegenerative diseases." Some
rescarch supports the assumption that it may protect body tissues from oxidative and ultraviolet damage through its
suppression of NF-KB activation. 3111
A.2015 meta-analysis of data from ten randomized, controlled trial groups in seven published clinical trials, doses
ranging 4 to 20 mg/day, did not indicate a significant effect of supplementation with astaxanthin on plasma lipids
profile or fasting glucose.!33)
Role in the food chain
It has been speculated that gulls are "flushed" pink when molting, especially in areas with farm-raised salmoa,41
However, not enough is known about the relationship between astaxanthin and plumage.{35] For example, cardinals
seem to produce astaxanthin from carotenoids when molting, even when fed primarily seed with natural yellow
dye.
os neamen Astaxanthin Wikipedia
Lobsters, shrimp, and some crabs turn red when cooked because the astaxanthin, which was bound to the protein in
the shell, becomes free as the protein denatures and unwinds. The freed pigment is thus available to absorb light
and produce the red color!
Regulations
In April 2009, the United States Food and Drug Administration approved astaxanthin as an additive for fish feed
only as a component of a stabilized color additive mixture. Color additive mixtures for fish feed made with
astaxanthin may contain only those diluents that are suitable.|") The color additives astaxanthin, ultramarine blue,
canthaxanthin, synthetic iron oxide, dried algae meal, Tagetes meal and extract, and com endosperm oil are
approved for specific uses in animal foods.27 Haematococcus algae meal (21 CFR 73.185) and Phaffia yeast (21
CFR 73.355) for use in fish feed to color salmonoids were added in 000.0191) In the European Union,
astaxanthin-containing food supplements derived from sources that have no history of use as a source of food in
Europe, fall under the remit of the Novel Food legislation, EC (No.) 258/97. Since 1997, there have been five
novel food applications concerning products that contain astaxanthin extracted from these novel sourees. In each
case, these applications have been simplified or substantial equivalence applications, because astaxanthin is
recognised as a food component in the EU diet [#!I421143]/4)
References
1. SciFinder Web (accessed Sep 28, 2010). Astaxanthin (472-61-7) Name
2. SciFinder Web (accessed Sep 28, 2010). Astaxanthin (472-61-7) Experimental Properties,
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‘mechanism of action of astaxanthin: IIT. Antioxidant and histopathological effeets in spontaneously hypertensive rats”
Biol, Pharm, Bull. 29 (4): 684-8, doi:10.1248/bpb.29.684. PMID 16595899.
4, Margalith, P. Z. (1999). "Production of ketocarotenoidls by microalgae". Applied microbiology and biotechnology. 51 (4
431-8. doi:10.1007/s002530051413. PMID 10341427.
5, Choi, Seyoung: Koo, Sangho (2005), "Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and
Astacene”. The Journal of Organic Chemistry. 70 (8): 3328-31, doi:10,1021/jo0501011, PMID 15823009.
6, Cooper, R. D. G.; Davis, J. B.; Leftwiek, A, Ps Price, C.; Weedon, B. (1975). "Carotenoids and related compounds,
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dicon/article, php?id=365). aquafeed.com
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32
33
35,
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38,
39,
40,
41
4B
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See 21 CFR 73.35,73.50, 73.75, 73.200, 73.275, 73.295, 73.315, respectively.
Code of Federal Regulations Title 21 $73.35 FDA decision on Astaxanthin (htip:/www.accessdata, fda goviscripts/edrh/et
docs/efifi/CFR Scarch.cfin?fr=73.35). Accessdata.fla.gov. Retrieved on 2013-04-25.
Code of Federal Regulations Title 21 §73.185 FDA decision on Haematococeus algae meal (http://www.aecessdata. fda. 20
vscripts/odrhicfdocs/cfeti/CFRScarch.cfm?fi=73. 185). Accessdata.fida.gov, Retrieved on 2013-04-25,
Food Additive Status List (https://web.archive.org/web/20130314104055 hhttp://www.fda,gov/Food/FoodIngredientsPacka
ging/Food Additives’ FoodA dditiveLiscings/cm091048, htm). fda. gov}
Astaxanthin extract (https://web.archive.org/web/20110810075220/htip://aenfp. food. gov.uk/assess/simproc/astaxanthinest
Tact}. acnfp. food. gov.uk
Astaxanthin extract: Cyanotech Corporation (htips:/web.archive.ong/web/20101018 1845S8/htip://iwwwaentp.gov.ul/asses
s/simprociastacyan). acutp.gov.uk
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Iwassess/simproc/algaastax) acnfp.gov.uk
2007,
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44, Astaxanthin extract: Parry Nutraceuticals (https:/web.archive.org/web/201010181 84558 /httpy/www.aenfp.gov.uk/assess/s
improc/astaxextractparry/). acnfp.gov.uk
External links
= Development of microalgal pigments for aquaculture (https://web.archive.org/web/200603 13 143828/ht«p://w
ww, biomatnet.org:80/secure/Fair/R1518.hum) 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). (http://www.scielo.cl/scielo.php?pi
02004000100009&scriptsci_arttext)
= Multibudding in Xanthophyllomyces dendrorhous Cells Under Hydric and Nitrogen Stress [1] (hitps://web.2
e.org/web/200609280 14422 hhttp://www.microbelibrary.org/ASMOnly/details.asp?id=1971)
= The Effects of Three Carotenoid Sources on Growth and Pigmentation of Juvenile Freshwater Crayfish
Cherax quadricarinatus (https:/'web.archive.org/web/20060622 165707/hitp://vww.agri.gov.il:80/AnimalScie
nee/Aquaculture/Rep-Harpaz2.html)
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Categories: Food colorings | Carotenoids | Alcohols | Tetraterpenes
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