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Merck

SML0982

Astaxanthin

≥95% (HPLC), powder, PPARγ

Synonym(s):

(3S,3′S)-3,3′-dihydroxy-β,β-Carotene-4,4′-dione, trans-Astaxanthin

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About This Item

Empirical Formula (Hill Notation):
C40H52O4
CAS Number:
Molecular Weight:
596.84
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥95% (HPLC)
Form:
powder
Quality level:
Storage condition:
desiccated, protect from light
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Product Name

Astaxanthin, ≥95% (HPLC)

Quality Level

assay

≥95% (HPLC)

form

powder

storage condition

desiccated, protect from light

color

, pink to very dark purple

solubility

DMSO: 1 mg/mL (warmed)

storage temp.

−20°C

SMILES string

O[C@H]1CC(C(=C(C1=O)C)\C=C\C(=C\C=C\C(=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C2=C(C(=O)[C@H](CC2(C)C)O)C)\C)\C)(C)C

InChI

1S/C40H52O4/c1-27(17-13-19-29(3)21-23-33-31(5)37(43)35(41)25-39(33,7)8)15-11-12-16-28(2)18-14-20-30(4)22-24-34-32(6)38(44)36(42)26-40(34,9)10/h11-24,35-36,41-42H,25-26H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,27-15+,28-16+,29-19+,30-20+/t35-,36-/m0/s1

InChI key

MQZIGYBFDRPAKN-UWFIBFSHSA-N

General description

Astaxanthin (AST) is a red dietary carotenoid. It is mainly found in aquatic animals and microalgae, such as Haematococcus pluvialis and Chlorella zofingiensis.

Application

Astaxanthin has been used:
  • as an antioxidant to study its effect on Brachionus manjavacas (Rotifera) population growth
  • to study its effects on the treatment of diabetic retinopathy.
  • to investigate its role in restoring the expression of Nrf2 (nuclear factor erythroid 2 p45-related factor 2) and glutathione S-transferase P1 (GSTP1) through epigenetic modification in human prostate LNCaP cells.

Biochem/physiol Actions

Astaxanthin is a potent antioxidant with antiproliferative, neuroprotective and anti-inflammatory activity.
Astaxanthin is a potent antioxidant with antiproliferative, neuroprotective and anti-inflammatory activity. Astaxanthin protects against oxidative stress, inhibiting NF-KB, suppressing pro-inflammatory genes and suppressing production of pro-inflammatory compounds nitric oxide, prostaglandin E2, TNF-α, and interleukin-1β. Astaxanthin′s protection of cells from oxidative stress generated by TNF-α and palmitate has been shown to ameliorate insulin resistance. Astaxanthin has also been shown to be an inhibitor of PPARγ.
In vivo and in vitro studies propose that astaxanthin (AST) possesses health-promoting activities, signifying its potential use in the prevention of various diseases, such as cancers and Parkinson′s disease. Due to its bright red colour, AST has been used as a food colorant in animal feeds.

Other Notes

Light and air sensitive


Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable



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Epigenetic CpG methylation of the promoter and reactivation of the expression of GSTP1 by Astaxanthin in human prostate LNCaP cells.
Yang Y, et al.
The AAPS Journal, 19(2), 421-430 (2017)
Huilin Liu et al.
Marine drugs, 17(3) (2019-03-22)
Alcoholic liver disease (ALD) is a major cause of chronic liver disease worldwide. It is a complex process, including a broad spectrum of hepatic lesions from fibrosis to cirrhosis. Our previous study suggested that astaxanthin (AST) could alleviate the hepatic
Effects of astaxanthin on Brachionus manjavacas (Rotifera) population growth.
Johnston R K, et al.
Aquaculture Research, 49(6), 2278-2287 (2018)