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Sigma-Aldrich

Echinenone

≥95.0% (HPLC)

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Synonym(s):
β,β-Caroten-4-one
Empirical Formula (Hill Notation):
C40H54O
CAS Number:
432-68-8
Molecular Weight:
550.86
Beilstein:
2030114
EC Number:
207-083-4
MDL number:
MFCD06656303
PubChem Substance ID:
329764812
NACRES:
NA.32

Quality Level

100

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

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Paula Mapelli-Brahm et al.
Food chemistry, 300, 125232-125232 (2019-07-29)
The mechanisms of main tomato carotenes (phytoene, phytofluene, lycopene and β-carotene) intestinal absorption are still only partly understood. We thus compared carotene bioavailability in mice after gavage with carotene-rich oil-in-water emulsions. We also determined each carotene absorption profile along the
Fernando Muzzopappa et al.
Nature plants, 5(10), 1076-1086 (2019-09-19)
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
Veno Jaša Grujić et al.
Plants (Basel, Switzerland), 11(8) (2022-04-22)
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
Effects of acute hypoxic exposure on prooxidant/antioxidant balance in elite endurance athletes
Pialoux V, et al.
International Journal of Sports Medicine, 30(02), 87-93 (2009)
Echinenone vibrational properties: from solvents to the orange carotenoid protein
Kish E, et al.
Biochimica et Biophysica Acta - Bioenergetics, 1847(10), 1044-1054 (2015)
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