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通过全合成以及从天然糖苷橄榄苦苷制备高产率的羟基酪醇稳定前体。

High-yielding preparation of a stable precursor of hydroxytyrosol by total synthesis and from the natural glycoside oleuropein.

作者信息

Gambacorta Augusto, Tofani Daniela, Bernini Roberta, Migliorini Antonella

机构信息

Dipartimento di Ingegneria Meccanica e Industriale, Università degli studi Roma Tre, via della Vasca Navale 79, 00146 Roma, Italy.

出版信息

J Agric Food Chem. 2007 May 2;55(9):3386-91. doi: 10.1021/jf063353b. Epub 2007 Apr 6.

DOI:10.1021/jf063353b
PMID:17411065
Abstract

The unprecedented acetonide of the antioxidant hydroxytyrosol has been synthesized by a two-step high-yielding procedure and found to be both purifiable by chromatography and stable over a wide pH range. The protection stabilizes hydroxytyrosol against oxidation, thereby allowing long-term storage. The protection can quantitatively be removed, under nonaqueous conditions, to afford pure hydroxytyrosol suitable for use as an additive in food and cosmetic preparations. Extension of the same methodology to the natural and easily accessible glycoside oleuropein, followed by saponification of the resulting complex mixture of acetonides, allowed hydroxytyrosol acetonide to be recovered in high yield. This constitutes a new interesting methodology to obtain the antioxidant hydroxytyrosol.

摘要

抗氧化剂羟基酪醇的前所未有的丙酮化物已通过两步高产率程序合成,并发现其既可通过色谱法纯化,又能在很宽的pH范围内保持稳定。这种保护作用使羟基酪醇免受氧化,从而实现长期储存。在非水条件下,可以定量地去除这种保护作用,得到适合用作食品和化妆品添加剂的纯羟基酪醇。将相同的方法扩展到天然且易于获取的糖苷橄榄苦苷,然后对所得复杂的丙酮化物混合物进行皂化,使得能够高产率回收羟基酪醇丙酮化物。这构成了一种获得抗氧化剂羟基酪醇的新的有趣方法。

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