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73341

Echinenone

Name: Echinenone
Brand: SIGMA

≥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

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Product Name

Echinenone, ≥95.0% (HPLC)

Quality Level

100

assay

≥95.0% (HPLC)

form

solid

λ

in hexane (with 2% dichloromethane)

UV absorption

λ: 459 nm±5 nm A_max

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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)

Temperature and storage time increase provitamin A carotenoid concentrations and bioaccessibility in post-harvest carrots.

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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Global Trade Item Number

SKU	GTIN
73341-1MG	04061826688090

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