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MilliporeSigma

73341

Sigma-Aldrich

Echinenone

≥95.0% (HPLC), solid

Sinónimos:

β,β-Caroten-4-one

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About This Item

Fórmula empírica (notación de Hill):
C40H54O
Número de CAS:
Peso molecular:
550.86
Beilstein/REAXYS Number:
2030114
EC Number:
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.32

product name

Echinenone, ≥95.0% (HPLC)

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Immune status is more affected by age than by carotenoid depletion-repletion in healthy human subjects
Farges MC, et al.
The British Journal of Nutrition, 108(11), 2054-2065 (2012)
Reconstitution of gloeobacter rhodopsin with echinenone: role of the 4-keto group
Balashov SP, et al.
Biochemistry, 49(45), 9792-9799 (2010)
Isolation and identification of echinenone from Micrococcus roseus
Schwartzel EH and Cooney JJ
Journal of Bacteriology, 104(1), 272-274 (1970)
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)
The cyanobacterium Anabaena sp. PCC 7120 has two distinct beta-carotene ketolases: CrtO for echinenone and CrtW for ketomyxol synthesis
Mochimaru M, et al.
Febs Letters, 579(27), 6111-6114 (2005)

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