Contribution of sonic effect on the stereoisomerization and on the epoxidation of all-trans-β-carotene

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  • CONTRIBUTION OF SONIC EFFECT ON THE STEREOISOMERIZATION AND ON THE EPOXIDATION OF ALL-<i>TRANS</i>-β-CAROTENE
  • Contribution of sonic effect on the stereoisomerization and on the epoxidation of all-trans-ベータ-carotene

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Sonic effects on the stereoisomerization and on the epoxidation of all-trans-β-carotene were evaluated. The sample solution was sonicated using sonic oscillator (20kc/sec, 300w).<br>1. When submitted to sonication, all-trans-β-carotene underwent partial trans→cis isomerization. The extent of this phenomenon and its reproducibility were variable depending upon the kind of the solvent and the amounts of the isomers increased when a conventional photochemical or thermal treatment was used together. Apparent sonic effect for isomerization in the chloroform solution of the sample under non-additive and in the darkness reached to ca. 30% of the starting material treated and the highest yield of cis isomers amounted to 55% (neo U 22, neo B 27, neo D 4 and neo E 2%) when the hexane solution of all-trans compound containing catalytic amount of iodine was sonicated under illumination.<br>2. β-Carotene epoxides were prepared more easily in a short time by the sonic treatment of the hexane solution of β-carotene containing perphthalic acid. When perphthalic acid was used six times by weight of β-carotene, the sonication gave 5, 6-monoepoxide, 5, 6, 5′, 6′-diepoxide and 5, 8-monoepoxide in the yield of 26, 4 and 2%, respectively, and almost half of the starting material was recovered.<br>Little or no sonic effect was observed when the solution of β-carotene was sonicated during its air- or H2O2-oxidation.<br>3. β-Carotene epoxides were more stable than their parent hydrocarbon carotenoid, β-carotene.

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