Studies on the Synthesis of Cyclitol derivatives -Part 5. Synthesis of O-(p-hydroxybenzoyl)-inositols and their test for food industry-

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

Reduction of penta-O-acetyl-myo-inosose-2 by catalytic hydrogenation and with sodium-amalgam was carried out in alcohol solution of pH $3{\sim}4$. The former reduction product was axial-alcohol, and the latter equatorial-alcohol. On reduction of penta-O-acetyl-DL-epi-inosose-2 with sodium borohydride and sodium-amalgam in the previous condition, ax.-alcohol and eq.-alcrhol have been obtained. The synthesis of various inositol-p-hydroxybezoate are described. The esters have been characterized by paper chromatography and saponification, and their antimicrobial activities on some microbes were tested for the application of food industry. As the result, it was found that the antimicrobiol activity of epi-inositol ester was superior to its analogues.

1. myo-inositol의 산화(酸化) 생성물(生成物)인 inosose를 환원(還元)하여 ax.- 및 eq.-alcohol에 도달(到達)시켰다. 2. 2-O-(p-hydroxybenzoyl)-myo-inositol [IX], 4-O-(p-hydroxybenzoyl)-myo-inositol [X], O-(p-hydroxybenzoyl)-scyllo-inositol [XX], 그리고 2-O-(p-hydroxybenzoyl)-epi-inositol [XXVI] 등(等) 신화합물(新化合物) 4종(種)을 합성(合成)하였고 이것을 얻기 위하여 합성(合成)한 [V], [VI], [VII], [VIII], [XVIII], [XIX], [XXIV], [XXV] 등(等) 8종(種) 화합물(化合物)도 아직까지의 문헌(文獻)에 기재(記載)가 없는 화합물(化合物)들이다. 3. 여기서 합성(合成)한 ester [IX] [X], [XX], [XXVI] 4종(種)은 모두 항균력(抗菌力)이 나타나며 epi-inositol ester [XXVI] 의 Aspergillus oryzae에 대(對)한 항균력(抗菌力)이 가장 강력(强力)하게 나타난다. 이와 같이 항균력(抗菌力)은 화합물(化合物)의 입체구조(立體構造)와 관련(關聯)되는 것 같다.