Oxidation of 7-ethyl-2,3,5,6,8-pentahydroxy-1,4-naphthoquinone (echinochrome A) by atmospheric oxygen 1. Structure of dehydroechinochrome

被引：8
作者：
Novikov, V. L. [1 ]
Shestak, O. P. [1 ]
Mishchenko, N. P. [1 ]
Fedoreev, S. A. [1 ]
Vasileva, E. A. [1 ]
Glazunov, V. P. [1 ]
Artyukov, A. A. [1 ]
机构：
[1] Russian Acad Sci, GB Elyakov Pacific Inst Bioorgan Chem, Far Eastern Branch, 159 Prospekt 100 Let Vladivostoku, Vladivostok 690022, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2018年 / 67卷 / 02期
基金：
俄罗斯基础研究基金会;
关键词：
polyhydroxy-1,4-naphthoquinones; naphthazarins; sea urchin pigments; echinochrome A; 7-ethyl-2,3,5,6,8-pentahydroxy-1,4-naphthoquinone; antioxidants; oxidation; triplet oxygen; singlet oxygen; intramolecular hydrogen bonds; green chemistry; SINGLET OXYGEN; IR-SPECTROSCOPY; POLYHYDROXYNAPHTHOQUINONES; 1,3-DIKETONES; TAUTOMERISM; DERIVATIVES; CHEMISTRY;
D O I：
10.1007/s11172-018-2071-1
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The nondestructive oxidation of 7-ethyl-2,3,5,6,8-pentahydroxy-1,4-naphthoquinone by atmospheric oxygen in the ground (triplet (3)Sigma(-)(g)) and excited (singlet (1)Delta(g)) states in different solvents (acetone, dioxane, ethanol, aqueous ethanol, water) at room temperature involves the initial formation of 7-ethyl-5,6,8-trihydroxy-2,3-dioxo-2,3-dihydro-1,4-naphthoquinone (dehydroechinochrome) accompanied by the release of an H2O2 molecule into the reaction medium. Dehydroechinochrome, being highly susceptible to hydration, successively reacts with two H2O molecules to form 7-ethyl-2,2,3,3,5,6,8-heptahydroxy-2,3-dihydro-1,4-naphthoquinone as the relatively stable final product. In this form, it can be isolated from the mixture of reaction products.
引用
收藏
页码：282 / 290
页数：9
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