Studies on the Synthesis of Cyclitol derivatives -Part 6. Synthesis of O-(5-nitro-2-furoyl)-inositols and their test for food industry-

Cyclitol 유도체(誘導體) 합성(合成)에 관(關)한 연구(硏究) -제(第)6보(報) O-(5-nitro-2-furoyl)-inositol류(類)의 합성(合成)과 식품공업상(食品工業上) 응용(應用)을 위한 시험(試驗)-

In the previous work, as we have reported on the reduction of penta-O-acetyl-myo-inosose-2 and penta-O-acetyl-DL-epi-inosose-2, axial and equatorial alcohol have been produced. The synthesis of various inositol 5-nitro-2-furoate are described. The esters have been obtained by reaction of 5-nitro-2-furoylchloride with inositol stereomers in chloroform at low temperature. The ester have been characterized by paper chromatography and other determination. For the applicable purpose of food industry, their antimicrobial activities on microbes were tested, and it was found that the antimicrobial activity of muco-inositol ester was superior to the others, and considered that result would be related to the stereochemical structure.

1. myo-inositol에서 산화(酸化), 환원반응(還元反應)을 거쳐서 scyllo-[XVI], epi-inositol[XXI], ax.-과 eq.-alcohol[III],[IV],[XXIII],[XXIV]등(等)에 도달(到達)시켰고, muco-inositol[XXIX]을 합성(合成)하였다. 2. inositol stereomer의 5-nitrofuroic acid ester인 8종(種) 신화합물(新化合物)을 합성(合成)하였다. 즉 hexakis-O-(5-nitro-2-furoyl)-myo-inositol [IX], hexakis-O-(5-nitro-2-furoyl)-scyllo-inositol [XXI], hexakis-O-(5-nitro-2-furoyl)-epi-inositol [XXVII], hexakis-O-(5-nitro-2-furoyl)-muco-inositol [XXXII], 2-O-(5-nitro-2-furoyl)-myo-inositol [VII], 4-O-(5-nitro-2-furoyl)-myo-inositol [VIII], O-(5-nitro-2-furoyl)-scyllo-inositol [XX], 그리고 2-O-(5-nitro-2-furoyl)-epi-inositol [XXVI] 등(等)이다. 3. 이 8종(種) ester는 모두 항균력(抗菌力)이 있고, scyllo-, myo-, epi-, muco-inositol ester 의 순(順)으로 증대(增大)되는 경향(傾向)이 있으며 항균력(抗菌力)은 ester의 입체구조(立體構造)와 관련(關聯)되는 것이라 생각된다.