28999-90-8

Basic information

• Product Name: β-carotene-4,4'-dione
• CAS NO: 28999-90-8
• Molecular Weight: 564.852
• Mol File: 28999-90-8.mol

Chemical Properties

• CAS DataBase Reference: β-carotene-4,4'-dione(CAS DataBase Reference)
• NIST Chemistry Reference: β-carotene-4,4'-dione(28999-90-8)
• EPA Substance Registry System: β-carotene-4,4'-dione(28999-90-8)

Safety Data

• Hazardous Substances Data: 28999-90-8(Hazardous Substances Data)

Upstream product

• 1186310-31-5 C₁₀H₁₄Cl₂ 
• 1186310-30-4 C₂₉H₃₆O₅S₂ 
• 1186310-33-7 C₆₈H₈₄O₁₀S₄ 
• 161023-01-4 β-carotene 
• 514-78-3 canthaxanthin 

Downstream Products

• 125377-14-2 4'-hydroxyechinenone 

Relevant articles and documents

Method for preparing canthaxanthin through oxidation

The invention discloses a method for preparing canthaxanthin through oxidation.The method includes the steps that beta-carotene serves as the raw material, sulfur oxide urea or urea peroxide serves as an oxidizing agent, an oxidizing reaction is conducted, and the canthaxanthin is obtained.The method has the advantages that operation is simple, the reaction is stable, and the trigger condition is mild; the oxidizing agents including sulfur oxide urea and urea peroxide can be decomposed into H2O2 and elemental oxygen in solvent, O2 is released slowly, the content of active oxygen is high, stability is high, the utility of time is long, no side effect exists, no toxin or public hazard exists, and it is beneficial to achieve industrialized clean production.

SULFONE COMPOUND AND CAROTENOID MANUFACTURING METHOD USING SAID COMPOUND

The present invention relates to a process for producing a sulfone compound of the following formula (3), characterized in that an allyl sulfone compound of the formula (1) and an allyl halide compound of the formula (2) are reacted in an organic solvent in the presence of an alkali metal hydroxide and a phase-transfer catalyst: wherein A is CH2 or C=O; Ar is an aryl group optionally having 1 to 3 substitutents; and the wavy line means that the steric relation to the double bond which the wavy line is bound to is of E-form, Z-form or a mixture of E/Z; wherein X is a halogen atom; and the wavy line means the same as defined above; and wherein A, Ar and the wavy line mean the same as defined above. The present invention also relates to a process for producing a carotenoid from the same sulfone compound.

Application of diphenyl diselenide as a new catalyst for photochemical stereoisomerization of carotenoids

In a comparative study, diphenyl diselenide was shown to be an alternative to iodine as a catalyst for photochemical E/Z isomerization of carotenoids. Suitable conditions for the stereomutation of zeaxanthin, violaxanthin, canlhaxanthin and fucoxanthin are reported. Photochemical allenic isomerization with increased R to S conversion was achieved by employing diphenyl diselenide rather than iodine as the catalyst. Reproducible and expedient artificial light conditions, avoiding insolation (sunlight), are reported. Diphenyl diselenide tolerated the presence of Huenig's base upon stereoisomerization of acid-sensitive carotenoids. Diphenyl ditelluride effected E/Z stereomutation, but no allenic R/S isomerization of fucoxanthin. The presence of base decreased the isomerization rate in the absence of catalyst and may serve to decrease undesirable E/Z stereoisomerization of base-stable carotenoids. Acta Chemica Scandinavica 1998.

Semiconductor photocatalysis: Photodegradation and trans-cis photoisomerization of carotenoids

In the presence of semiconductor CdS or ZnO particles, irradiation (>350 nm) of all-trans-β-carotene (II) in dichloromethane leads to rapid degradation of the carotenoid, which is relatively stable in the absence of the semiconductors. Canthaxanthin (I), however, undergoes significant photocatalyzed degradation only on ZnO, not on CdS. High-performance liquid chromatographic studies indicate that CdS catalyzes trans-cis photoisomerization of both I and II. As in the photoisomerization in the absence of semiconductor, the major cis isomers have the 9-cis and 13-cis configuration, but, under otherwise the same condition, the ratio of cis/trans isomers has doubled. In contrast to CdS, ZnO does not catalyze the photoisomerization of either I or II, although it enhances their rate of degradation. A photoisomerization mechanism involving carotenoid radicals formed by reaction with interstitial sulfur on the CdS surface is proposed.

Selected cis/trans isomers of carotenoids formed by bulk electrolysis and iron(III) chloride oxidation

Bulk electrolysis and chemical oxidation with FeCl3 of all-trans canthaxanthin (I) and 8′-apo-β-caroten-8′-al (II) gave primarily the 9- and 13-cis-isomers, which were separated by HPLC and identified by 1H NMR spectroscopy. Optical absorption measurements showed that the 15-cis, 9,13-di-cis isomers of I are also formed by these methods. In the case of the unsymmetrical compound II, additional isomers were formed. The cis isomers account for about 40-60% of products formed. Formation of the isomers is believed to occur by rotation about certain bonds in the cation radicals or dications, which are formed in the oxidation processes. The neutral cis species are then formed by an electron exchange reaction of the cis-cation radicals with neutral all-trans carotenoids in solution. The electrochemical and iron(III) chloride oxidation induced isomerization are shown to be efficient and improved methods for forming selected carotenoid isomers.