夏蜜柑果汁製造に関する基礎的研究(第22報) : フルフラールのレダクトン類似性

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During the browning of an acidic aqueous system such as orange juice, furfurals are formed, and they acquire reductone-like reducing power by acid hydrolysis. It is presumable that the reductone-like reducing substance possesses the structure of furfural without furan ring closure. α, α'-dihydroxymuconic acid is a true reductone. It has a conjugated dienediol, rather than an enediol-(α) ; nevertheless, the two enolic hydroxyls are readily dehydrogenated to give the dehydro-from. Furfural can be led to the conjugated dienediolic form by hydrolytic scission of the ring. The rupture of the furfural ring, such as shown in RCO-C(OH)=CH-CH=C(OH)-R', is known to take place in its hydrolytic scission or in the STENHOUSE reaction. As it is known that the open chain of dienediolic substances such as 2-ketoglutaraldehyde undergoes again the ring closure to furan derivatives via reductinic acid (Ref. : Helv. Chem. Acta., 16,988 (1933), 17,387 (1934) : J. Agric. Chem. Soc. Japan, 30,387 (1956)), the author proposes the browning mechanism of fufurals as follows : [chemical formula]In the STENHOUSE reaction, furfural reacts with aniline hydrochloride and produces lphenylimio-5-phenylamino-2-hydroxy-penta-2,4-diene, which bears much resemblance to Von EULER's reductone monoanil in its structure, and the compound so produced undergoes the ring closure to form pyridine derivative (l-phenyl-3-hydroxypyridium chloride). The formation of pyridine in this way might explain the fact that pyridines had been obtained by distillation from melanoidins.
公益社団法人日本生物工学会の論文
1956-10-15

著者

野村男次
山口大学農学部

夏蜜柑果汁製造に関する基礎的研究(第22報) : フルフラールのレダクトン類似性

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