432-68-8 Usage
Description
ECHINENONE, also known as 4-keto-β-carotene, is a monoketo compound and a carotenoid with a conjugated carbonyl group. It serves as an intermediate between β-carotene and canthaxanthin in animals and is one of the major carotenoids found in Anabaena sp. and Micrococcus roseus. Echinenone is located in the thylakoid membrane of Anabaena, and its conversion from β-carotene is catalyzed by CrtO, a β-carotene ketolase. It is widely distributed in marine invertebrates and is isolated as orange-red crystals.
Uses
Used in Analytical Chemistry:
ECHINENONE is used as an external standard for the extraction of carotenoids from plasma samples. This application is due to its stability and specificity in the extraction process, allowing for accurate quantification of carotenoids in various samples.
Used in Internal Standardization:
ECHINENONE is used as an internal standard, added to samples for extraction and quantification. Its role is to ensure the accuracy and reliability of the results by accounting for variations in the extraction process and providing a reference point for comparison.
Used in Pharmaceutical and Biotechnology Industries:
ECHINENONE, being a carotenoid, may have potential applications in the pharmaceutical and biotechnology industries due to its antioxidant properties and its role in various biological processes. However, the specific applications and reasons for its use in these industries are not provided in the given materials.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 432-68-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,3 and 2 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 432-68:
(5*4)+(4*3)+(3*2)+(2*6)+(1*8)=58
58 % 10 = 8
So 432-68-8 is a valid CAS Registry Number.
InChI:InChI=1/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+
432-68-8Relevant articles and documents
Preparation method of echinenone
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Paragraph 0044-0050; 0052-0059; 0060-0067; 0068-0083, (2020/05/14)
The invention discloses a preparation method of echinenone. According to the method, beta-apo-12 '-carotenal is oxidized into 4-oxo-beta-apo-12'-carotenal through regioselective oxidation, and then aC15 fragment is connected through a Witting reaction, so that the echinenone can be synthesized through a short-circuit line under the conditions of mild reaction conditions and simple process operation. The method has the advantages of short synthetic route, considerable product purity and yield, easily available raw materials, low cost, better industrial value, easiness in operation in the production process, no generation of toxic and harmful intermediates, and accordance with the concept of green and environment-friendly chemistry.
New methods for the synthesis of oxygenated carotenoids.
Surmatis,Walser,Gibas,Schwieter,Thommen
, p. 974 - 990 (2007/10/10)
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