5,6-单环氧维生素A醋酸酯、5,6-单环氧维生素A醇、5,6-单环氧维生素A醛及其相应的5,8-单环氧（呋喃型）化合物的制备与性质
PREPARATION AND PROPERTIES OF 5,6-MONOEPOXYVITAMIN A ACETATE, 5,6-MONOEPOXYVITAMIN A ALCOHOL, 5,6-MONOEPOXYVITAMIN A ALDEHYDE AND THEIR CORRESPONDING 5,8-MONOEPOXY (FURANOID) COMPOUNDS.
作者信息
JUNGALWALA F B, CAMA H R
出版信息
Biochem J. 1965 Apr;95(1):17-26. doi: 10.1042/bj0950017.
Abstract
- Oxidation of vitamin A acetate with monoperphthalic acid gave 5,6-monoepoxyvitamin A acetate, C(22)H(32)O(3), obtained as pale-yellow crystals, m.p. 65-66 degrees . 2. Saponification of 5,6-monoepoxyvitamin A acetate yielded 5,6-monoepoxyvitamin A alcohol, which was readily oxidized with manganese dioxide to 5,6-monoepoxyvitamin A aldehyde, obtained as yellow crystals, m.p. 101-102 degrees . It was the most stable of all the epoxy compounds studied. 3. Treatment of the 5,6-epoxy compounds with ethanolic hydrochloric acid gave the corresponding 5,8-epoxy (furanoid) compounds. 5,8-Monoepoxyvitamin A aldehyde was obtained as crystals, m.p. 104-105 degrees , but was very unstable. 4. Crystalline semicarbazones and phenylhydrazones with constant melting points and characteristic spectra were prepared from 5,6- and 5,8-monoepoxyvitamin A aldehyde. 5. Reduction of 5,6- and 5,8-monoepoxyvitamin A aldehyde with lithium aluminium hydride gave the corresponding 5,6- and 5,8-monoepoxyvitamin A alcohol. 6. 5,6- and 5,8-Monoepoxyvitamin A aldehyde were fed to vitamin A-deficient rats, and the compounds obtained from the livers of rats were indistinguishable from the reduction products obtained with lithium aluminium hydride. 7. The structures of the epoxy compounds were confirmed by their chromatographic behaviour, elemental analyses, ultraviolet-, visible- and infrared-absorption spectra and nuclear-magnetic-resonance spectra.
摘要
- 用单过邻苯二甲酸氧化维生素A醋酸酯得到5,6-单环氧维生素A醋酸酯，化学式为C(22)H(32)O(3)，呈浅黄色晶体，熔点65 - 66摄氏度。2. 5,6-单环氧维生素A醋酸酯皂化得到5,6-单环氧维生素A醇，它很容易被二氧化锰氧化为5,6-单环氧维生素A醛，呈黄色晶体，熔点101 - 102摄氏度。它是所有研究的环氧化合物中最稳定的。3. 用乙醇盐酸处理5,6-环氧化合物得到相应的5,8-环氧（呋喃型）化合物。5,8-单环氧维生素A醛呈晶体状，熔点104 - 105摄氏度，但非常不稳定。4. 由5,6-和5,8-单环氧维生素A醛制备出具有恒定熔点和特征光谱的结晶半缩醛腙和苯腙。5. 用氢化铝锂还原5,6-和5,8-单环氧维生素A醛得到相应的5,6-和5,8-单环氧维生素A醇。6. 将5,6-和5,8-单环氧维生素A醛喂给维生素A缺乏的大鼠，从大鼠肝脏中得到的化合物与用氢化铝锂得到的还原产物无法区分。7. 通过环氧化合物的色谱行为、元素分析、紫外、可见和红外吸收光谱以及核磁共振光谱确定了其结构。
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