Synthesis and evaluation of a new water‐soluble fluorescent red dye, xanthene bis‐C‐glycoside,Journal of Heterocyclic Chemistry

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Synthesis and evaluation of a new water‐soluble fluorescent red dye, xanthene bis‐C‐glycoside
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-07-15 , DOI: 10.1002/jhet.4050
Shingo Sato ₁ , Toshikatsu Nojiri ₁ , Nao Okuyama ₁ , Koya Maeda ₁ , Aoi Kirigane ₂

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Condensation of 2 eq. of C‐β‐D‐glucosylphloroacetophenone with glyoxylic acid in an aqueous solution of Na₂CO₃, followed by air oxidation in MeOH in the presence of 11 eq. of pyridine to afford a 36% yield of a bright red dye, xanthene bis‐C‐glycoside. This dye is 10 times more fluorescent (Φ_{f [EtOH]}^{581 nm} = 3.9 × 10⁻²) and 7.5 times more water‐soluble (57 mg/mL H₂O) than the natural red pigment, carthamin. Detailed NMR analysis of its methyl analogs was used to confirm the structure of the dye as methyl 4,5‐diacetyl‐1,3,8‐trihydroxy‐3‐oxo‐3H‐2,7‐di‐C‐β‐D‐glucopyranosylxanthene‐9‐carboxylate from among three possible ring‐closure isomers. Xanthene is safe and shows high light‐resistance; therefore, xanthene bis‐C‐glycoside could be used as a food colorant or an in vivo probe.

中文翻译：

新型水溶性荧光红染料x吨双-C-糖苷的合成与评价

2 eq。的冷凝的Ç - β -D- glucosylphloroacetophenone与乙醛酸的Na的水溶液₂ CO ₃，接着在MeOH中11当量的存在下空气氧化。吡啶可得到36％的鲜红色染料x吨双C-糖苷。该染料的荧光强度（Φf _[EtOH]^{581 nm} = 3.9×10 ^-2）是天然红色颜料红花素的10倍，水溶性（57 mg / mL H ₂ O）则是7.5倍。其甲基类似物的详述NMR分析用于证实染料的结构如甲基-4,5-二乙酰基-1,3,8-三羟基-3-氧代-3- ħ -2,7-二- Ç - β三种可能的闭环异构体中的-D-吡喃葡萄糖基蒽并蒽-9-羧酸盐。an吨是安全的，并具有很高的耐光性。因此，呫吨二Ç糖苷可作为食品着色剂或体内探针。

更新日期：2020-09-08

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