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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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Echinenone vibrational properties: from solvents to the orange carotenoid protein
Kish E, et al.
Biochimica et Biophysica Acta - Bioenergetics, 1847(10), 1044-1054 (2015)
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)
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)
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)
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

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