ECHINENONE Chemical Properties

Melting point:

178-180°

Boiling point:

685.3±25.0 °C(Predicted)

Density 

0.972±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Chloroform (Slightly), Diethyl Ether (Slightly), Methanol (Slightly)

form 

Solid

color 

Dark Red to Very Dark Red

λmax

λ: 459 nm±5 nm Amax

BRN 

2030114

Stability:

Light Sensitive, Temperature Sensitive

Safety Information

WGK Germany 

3

ECHINENONE Usage And Synthesis

Uses

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.

Definition

ChEBI: A carotenone that is beta-carotene in which the 4 position has undergone formal oxidation to afford the corresponding ketone. Isolated as orange-red crystals, it is widely distributed in marine invertebrates.

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.

Biochem/physiol Actions

Echinenone binds to glocobacter rhodopsin and functions as a light harvesting antenna in Gloeobacter violaceous.

Purification Methods

Purify β,β-caroten-4-one by chromatography on partially deactivated alumina or magnesia, or by using a thin layer plate of silica gel G with 4:1 cyclohexane/diethyl ether as the developing solvent. Recrystallise it from *C6H6/MeOH. Store it in the dark at -20o. The oxime crystallises from *C6H6 with m 208o. [Beilstein 7 III 2858, 7 IV 1881.]

ECHINENONE(432-68-8)Related Product Information

• Astaxanthin
• (3S,3'S,5R,5'R)-3,3'-dihydroxy-.kappa.,.kappa.-carotene-6,6'-dione
• CAPSANTHIN
• Lycopene
• Carotene
• ETHYL BETA-APO-8'-CAROTENOATE (TRANS)
• Zeaxanthin
• β-Carotene
• γ-Carotene
• torularhodin
• VIOLAXANTHIN
• Fucoxanthin
• Bixin
• Canthaxanthin
• (9-cis,9'-cis)-7,7',8,8'-tetrahydro-y,y-Carotene
• 3,7,12,16,20,24-hexamethyl-1-[(1R)-2,6,6-trimethyl-1-cyclohex-2-enyl]pentacosa-1,3,5,7,9,11,13,15,17,19,23-undecaene
• ECHINENONE
• BETA-CAROTENE