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Merck
CN

41659

all-trans-Astaxanthin

analytical standard

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C40H52O4
CAS Number:
472-61-7
Molecular Weight:
596.84
E Number:
E161j
PubChem Substance ID:
329756132
UNSPSC Code:
85151701
NACRES:
NA.24
EC Number:
207-451-4
MDL number:
MFCD00672621

Key Documents

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Product Name

all-trans-Astaxanthin, analytical standard

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

SMILES string

CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C([C@@H](O)CC2(C)C)=O)C(C)(C)C[C@H](O)C1=O

grade

analytical standard

assay

≥97%

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

cleaning products
cosmetics
food and beverages
personal care

format

neat

storage temp.

−20°C

Quality Level

100

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
all-trans-Astaxanthin may be used as an analytical reference standard for the quantification of the analyte in:
  • Microalgae (Green algae), Haematococcus pluvialis using high-performance liquid chromatography (HPLC) with mass spectrometric and fluorescence detection (HPLC-FLD).
  • Parapenaeopsis hardwickii using high-performance liquid chromatography (HPLC) with photodiode array detection (PDA).

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.

General description

all-trans-Astaxanthin belongs to the class of carotenoids. It 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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM9965
BCCJ2788
BCCF9580
BCCC8628
BCBZ9727

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Chromatographic separation and purification of trans-astaxanthin from the extracts of Haematococcus pluvialis
Yuan P-J and Chen F
Journal of Agricultural and Food Chemistry, 46(8), 3371-3375 (1998)
Determination of carotenoids in spear shrimp shells (Parapenaeopsis hardwickii) by liquid chromatography
Lin C-W, et al.
Journal of Agricultural and Food Chemistry, 53(13), 5144-5149 (2005)
P F Zagalsky
Acta crystallographica. Section D, Biological crystallography, 59(Pt 8), 1529-1531 (2003-07-24)
The crystal structure of a beta-crustacyanin allows an analysis of the various proposals for the mechanism of the bathochromic shift from orange to purple-blue of astaxanthin in this lobster carotenoprotein. Structural and previous chemical and biophysical studies suggest that extension
Determination of astaxanthin and astaxanthin esters in the microalgae Haematococcus pluvialis by LC-(APCI) MS and characterization of predominant carotenoid isomers by NMR spectroscopy
Holtin K, et al.
Analytical and Bioanalytical Chemistry, 395(6), 1613-1613 (2009)
R T Lorenz et al.
Trends in biotechnology, 18(4), 160-167 (2000-03-31)
As a result of high production costs, commercial products from microalgae must command high prices. Astaxanthin produced by Haematococcus is a product that has become a commercial reality through novel and advanced technology. Cultivation methods have been developed to produce
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