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HomeProduct name listAstaxanthin

Astaxanthin

Synonym(s):Astaxanthin;trans-Astaxanthin;(3S,3′S,all-trans)-3,3′-Dihydroxy-β,β-carotene-4,4′-dione;(3S,3′S)-3,3′-Dihydroxy-β,β-carotene-4,4′-dione;(3S,3′S)-3,3′-Dihydroxy-β,β-Carotene-4,4′-dione

  • CAS NO.:472-61-7
  • Empirical Formula: C40H52O4
  • Molecular Weight: 596.85
  • MDL number: MFCD00672621
  • EINECS: 207-451-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-15 19:19:13
Astaxanthin Structural

What is Astaxanthin?

Description

Astaxanthin, a member of the carotenoid family, is part of a nutritious diet—for lobsters and shrimp. These crustaceans bind astaxanthin to the protein β-crustacyanin, which changes the shape of the astaxanthin molecules, turning them a gray-blue color. Cooking releases the molecules, returning them to their original bright red color.

Chemical properties

Drak-Purple Solid

The Uses of Astaxanthin

Astaxanthin is a carotenoid pigment found primarily in marine animals including shrimp and salmon. It is a potent lipid-soluble antioxidant.

The Uses of Astaxanthin

Carotenoid pigment found mostly in animal organisms, but also occuring in plants; thought to be the precursor of astacin. Animal studies indicate that it reduces blood glucose and ameliorates several parameters of the diabetic metabolic syndrome. It improves blood flow and vascular tone in models of hypertension.

The Uses of Astaxanthin

astaxanthin is an anti-oxidant. Molecularly, astaxanthin is similar to beta-carotene, but in clinical studies it appears to demonstrate stronger anti-oxidant properties, including an ability to inhibit lipid peroxidation and an anti-inflammatory capacity. It is used in cosmetics for its anti-oxidant properties, and for possible uV protection abilities. Astaxanthin is a naturally occurring pigment, part of the carotenoid group, and found in many foods. It is what provides salmon and certain crustaceans (e.g., shrimp, crab, lobster) with their reddish tint. Astaxanthin can also be synthetically produced.

Definition

ChEBI: Astaxanthin is a carotenone that consists of beta,beta-carotene-4,4'-dione bearing two hydroxy substituents at positions 3 and 3' (the 3S,3'S diastereomer). A carotenoid pigment found mainly in animals (crustaceans, echinoderms) but also occurring in plants. It can occur free (as a red pigment), as an ester, or as a blue, brown or green chromoprotein. It has a role as an anticoagulant, an antioxidant, a food colouring, a plant metabolite and an animal metabolite. It is a carotenone and a carotenol. It derives from a hydride of a beta-carotene.

Biotechnological Production

Commercial production processes are known in which astaxanthin production is performed in closed photobioreactors by Cyanotech Corporation (Hawaii). This mode of cultivation strongly improves process control, algae predation, and production, but the fermentation costs are significantly higher. These higher costs have to be compensated by high productivity levels and more efficient downstream processing in order to make a competitive product.
Most of the astaxanthin available on the world market has been produced chemically since the 1950s, for example, by DSM and BASF, and the process is efficient and cost-effective. There are also microbial sources, for example, X. dendrorhous (previously described as P. rhodozyma), and the alga H. pluvialis. X. dendrorhous has been widely investigated as to its potential of astaxanthin production for salmonids. This has resulted in a race between companies in the 1980s and 1990s. Natural astaxanthin is currently available as a spray-dried powder (5–10 mg astaxanthin/g), and is supplemented to fish feed to give salmonid flesh its pink color. Another astaxanthin application is in the nutraceutical market, as astaxanthin is regarded as a potential antioxidant. With regard to production by algae, H. pluvialis is the only species commercially cultivated for astaxanthin production. This green alga is able to grow under autotrophic, heterotrophic, and mixotrophic conditions. An example of the latter is its ability to grow in the presence of acetate and light. Astaxanthin accumulates in response to stress in lipid globules of the cells.

General Description

all-trans-Astaxanthin is a ketocarotenoid, most commonly identified in marine and aquatic animals, including krill, wild salmon, rainbow trout, microalgae, shells of lobster, shrimp, seafood products, etc. It is biologically known as a vitamin A precursor, and exhibits strong antioxidant property, much higher compared to vitamin E and β-carotene. Its role in food and the medicinal industry is also well-defined.

Biochem/physiol Actions

Astaxanthin is a potent carotenoid antioxidant found in marine algae, red yeast and many other plant and animal sources. Animal studies indicate that it reduces blood glucose and ameliorates several parameters of the diabetic metabolic syndrome. It improves blood flow and vascular tone in models of hypertension. In vitro studies indicate that it upregulates connexin 43 and thus, may be chemopreventive against cancer.

Properties of Astaxanthin

Melting point: 215-216 °C
Boiling point: 568.55°C (rough estimate)
Density  0.9980 (rough estimate)
refractive index  1.4760 (estimate)
storage temp.  -20°C
solubility  DMSO: soluble1mg/mL (warmed)
form  powder
pka 12.33±0.70(Predicted)
color  , pink to very dark purple
Stability: Light Sensitive
CAS DataBase Reference 472-61-7

Safety information for Astaxanthin

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
H412:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P271:Use only outdoors or in a well-ventilated area.
P273:Avoid release to the environment.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.
P405:Store locked up.
P403+P233:Store in a well-ventilated place. Keep container tightly closed.

Computed Descriptors for Astaxanthin

InChIKey MQZIGYBFDRPAKN-SODZLZBXSA-N
SMILES C(/C1=C(C(=O)[C@@H](O)CC1(C)C)C)=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C(=O)[C@@H](O)CC1(C)C)C |&1:5,37,r|

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