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73341

Sigma-Aldrich

Echinenone

≥95.0% (HPLC), solid

Synonym(s):

β,β-Caroten-4-one

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About This Item

Empirical Formula (Hill Notation):
C40H54O
CAS Number:
Molecular Weight:
550.86
Beilstein:
2030114
EC Number:
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.32

product name

Echinenone, ≥95.0% (HPLC)

Quality Level

Assay

≥95.0% (HPLC)

form

solid

λ

in hexane (with 2% dichloromethane)

UV absorption

λ: 459 nm±5 nm Amax

storage temp.

−20°C

SMILES string

CC(/C=C/C1=C(C)C(CCC1(C)C)=O)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(\C=C\C2=C(C)CCCC2(C)C)C

InChI

1S/C40H54O/c1-30(18-13-20-32(3)23-25-36-34(5)22-15-28-39(36,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-37-35(6)38(41)27-29-40(37,9)10/h11-14,16-21,23-26H,15,22,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+

InChI key

QXNWZXMBUKUYMD-QQGJMDNJSA-N

General description

Echinenone is a carotenoid with a conjugated carbonyl group. Echinenone (4-keto-β-carotene) is a monoketo compound, is an intermediate between β-carotene and canthaxanthin in animals. It is one of the major carotenoids of Anabaena sp., and also present in Micrococcus roseus. It is located in the thylakoid membrane of Anabaena. The conversion of β-carotene to echinenone is catalysed by CrtO, a β-carotene ketolase.

Application

Echinenone may be used as an external standard for the extraction of carotenoid from plasma samples. It may also been used as an internal standard, added to samples for extraction and quantification.

Biochem/physiol Actions

Echinenone binds to glocobacter rhodopsin and functions as a light harvesting antenna in Gloeobacter violaceous.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Fernando Muzzopappa et al.
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The photoactive orange carotenoid protein (OCP) is a blue-light intensity sensor involved in cyanobacterial photoprotection. Three OCP families co-exist (OCPX, OCP1 and OCP2), having originated from the fusion of ancestral domain genes. Here, we report the characterization of an OCPX
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Que Chen et al.
Photochemistry and photobiology, 93(3), 772-781 (2017-05-14)
Proteorhodopsins are light-driven proton pumps that occur widespread in Nature, where they function predominantly in environments with high incident irradiance. Their maximal absorbance is usually in the blue range, but can be extended into the (far)red range of the electromagnetic
Effects of exercise and training in hypoxia on antioxidant/pro-oxidant balance
Pialoux V, et al.
European Journal of Clinical Nutrition, 60(12), 1345-1345 (2006)
Veno Jaša Grujić et al.
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H. pluvialis is a unicellular freshwater alga containing many bioactive compounds, especially carotenoids, which are the strongest antioxidants among the pigments. This study evaluates the composition and content of carotenoids and other pigments in both stages of algae life cycle

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