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Merck
CN

73341

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:
432-68-8
Molecular Weight:
550.86
NACRES:
NA.32
PubChem Substance ID:
329764812
UNSPSC Code:
12352202
EC Number:
207-083-4
MDL number:
MFCD06656303
Beilstein/REAXYS Number:
2030114

Key Documents

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Product Name

Echinenone, ≥95.0% (HPLC)

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 key

QXNWZXMBUKUYMD-QQGJMDNJSA-N

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+

assay

≥95.0% (HPLC)

form

solid

λ

in hexane (with 2% dichloromethane)

UV absorption

λ: 459 nm±5 nm Amax

storage temp.

−20°C

Quality Level

100

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.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL5321
BCCN6827
BCCK9447
BCCH6391
BCCG3747

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Isolation and identification of echinenone from Micrococcus roseus
Schwartzel EH and Cooney JJ
Journal of Bacteriology, 104(1), 272-274 (1970)
Reconstitution of gloeobacter rhodopsin with echinenone: role of the 4-keto group
Balashov SP, et al.
Biochemistry, 49(45), 9792-9799 (2010)
Faiza Hammaz et al.
Food chemistry, 338, 128004-128004 (2020-09-21)
The aim was to enhance provitamin A carotenoid (proVA CAR) concentrations and bioaccessibility in carrots by manipulating post-harvest factors. To that end, we assessed the effects of Ultraviolet-C light, pulsed light, storage temperature, and storage duration. We also measured CAR
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)
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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