Tristin; 5-[2-(4-羟基-3-甲氧基苯基)乙基]-1,3-苯二酚 | 139101-67-0

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: Tristin; 5-[2-(4-羟基-3-甲氧基苯基)乙基]-1,3-苯二酚
• 中文别名: 5-[2-(4-羟基-3-甲氧基苯基)乙基]-1,3-苯二酚
• 英文名称: Tristin
• 英文别名: 5-[2-(4-hydroxy-3-methoxyphenyl)ethyl]benzene-1,3-diol
• CAS: 139101-67-0
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: KPFFMALTIRFAHW-UHFFFAOYSA-N

物化性质

• 沸点：
  452.9±35.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[2-(3-methoxy-4-phenylmethoxyphenyl)ethenyl]-3,5-bis(phenylmethoxy)benzene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以90%的产率得到Tristin; 5-[2-(4-羟基-3-甲氧基苯基)乙基]-1,3-苯二酚
  参考文献：
  名称：

  使用天然化感病化合物Batastasin-III及其合成类似物预防海洋生物污染

  摘要：

  本研究报告了对海洋环境中化感作用的陆地天然产物作为防污剂的首次综合评估。为了研究天然二氢二苯乙烯支架的防污潜力，制备了22种具有不同取代模式的合成二氢二苯乙烯类化合物的文库，并评估了它们的防污能力，其中许多取代型自然存在于陆生植物中。在针对16种污染海洋生物的广泛筛选中评估了这些化合物。研究表明，二氢二苯乙烯骨架对海洋微污垢和大型污垢均具有强大的一般防污效果，并在低浓度下具有抑制活性。在低ng / mL浓度下，所检查的微藻物种对所评估的化合物表现出特殊的敏感性。结果表明，几种天然和合成化合物均通过无毒和可逆的机制发挥其排斥作用。活性最高的化合物，例如3,5-二甲氧基联苄（5），3，4-二甲氧基联苄基（9）和3-羟基-3′，4，5′-三甲氧基联苄基（20）与用作防污助剂的商业防污剂Sea-n相当。陆地化感化天然产物对付海洋污染的研究代表了一种设计“绿色”防污技术的新颖策略，这些化合物为传统的杀生物防污剂提供了潜在的替代品。

  DOI：

  10.1021/acs.jnatprod.7b00129

文献信息

• Isolation, structure, and synthesis of a stilbene glucoside from the bark of: <i>Picea</i> <i>glauca</i> (moench) voss.
  作者：D. H. Andrews、J. C. Hoffman、C. B. Purves、H. H. Quon、E. P. Swan

  DOI：10.1139/v68-414

  日期：1968.8.1

  The fractionation of phlobaphenes from white spruce bark by column chromatography gave the non-crystalline stilbene glucoside trans 3,4′5-trihydroxy-3′-methoxystilbene-3-O-β-D-glucopyranoside (1). Purification was achieved through deacetylation of its hexaacetate (2). Compound 1 was cleaved with emulsin or dilute acid to the aglycone 4, and D-glucose. The acetate, benzoate, and dihydro-derivatives of 1, and the acetate, benzoate, methyl ether, and dihydro-derivatives of 4 were prepared. Oxidation of the benzoate derivative of 1 with chromic acid gave dibenzoyl-α-resorcylic acid. Similar oxidation of 2 gave acetylvanillic acid together with an uncharacterized acid which was hydrolyzed to D-glucose and β-resorcylic acid. The structure of 1 was therefore as shown, and its derivative 2 was synthesized. Vanillin was condensed with 3,5-dihydroxyphenylacetic acid and the product was decarboxylated and deacetylated. This compound was condensed with tetra-O-acetyl-α-D-glucopyranosyl bromide to yield a mixture of products which, after acetylation, were separated, using preparative thin-layer chromatography, to give the desired 2.

  用柱层析法从白云杉树皮中分离出phlobaphenes，得到了非结晶的stilbene葡萄糖苷trans 3,4′5-三羟基-3′-甲氧基stilbene-3-O-β-D-葡萄糖苷（1）。通过去乙酰化其六乙酸酯（2）实现了纯化。化合物1经乳酶或稀酸裂解为去糖基体4和D-葡萄糖。制备了化合物1的乙酸酯、苯甲酸酯和二氢衍生物，以及化合物4的乙酸酯、苯甲酸酯、甲醚和二氢衍生物。用高锰酸盐氧化化合物1的苯甲酸酯衍生物得到了二苯甲酰-α-邻苯二酚酸。对2进行类似氧化得到了乙酰香草酸和一个未表征的酸，后者水解为D-葡萄糖和β-邻苯二酚酸。因此，化合物1的结构如上所示，并合成了其衍生物2。香草醛与3,5-二羟基苯乙酸缩合，产物经脱羧和去乙酰化。将该化合物与四-O-乙酰-α-D-葡萄糖吡喃糖溴化物缩合，得到一系列产物混合物，经乙酰化后，使用制备性薄层色谱分离，得到所需的2。
• Method of using dihydro-resveratrol or its stilbenoid derivatives and/or chemical variants in treatment of tumorous pathologies
  申请人：Hong Kong Baptist University

  公开号：US10017442B2

  公开（公告）日：2018-07-10

  The present invention relates to a polyphenol derivative of the stilbenoid family, namely trans-3,5,4′-trihydroxybibenzyl, also known as dihydro-resveratrol, as a remedial agent. In particular, the present invention presents the usage of dihydro-resveratrol or its derivatives/chemical variants in the manufacture of a medicament for the treatment of tumors or cancers. The dihydrostilbenes can be used in the treatment or delay of progression of a cancer in a patient or used in a pharmaceutical formulation for the aforementioned purposes.

  本发明涉及一种白藜芦醇家族的多酚衍生物，即反式-3,5,4′-三羟基白藜芦醇，又称二氢白藜芦醇，可作为一种治疗剂。特别是，本发明提出了二氢白藜芦醇或其衍生物/化学变体在制造治疗肿瘤或癌症的药物中的用途。二氢白藜芦醇可用于治疗或延缓患者的癌症进展，或用于上述目的的药物制剂中。
• Skin-protection composition containing Dendrobium-based ingredients
  申请人：Hong Kong Baptist University

  公开号：US10188590B2

  公开（公告）日：2019-01-29

  The present invention relates to a skin-protection composition that comprises stilbenoid(s) and/or stilbenoid-containing extract(s) obtained from Dendrobium plants, such as Dendrobium officinale and Dendrobium nobile for the management of melanogenesis, skin-darkening and skin-aging. More particularly, it relates to the usage of Dendrobium ingredients and stilbenoids to reduce the formation of melanin in melanocytes. It also relates to the usage of Dendrobium ingredients and stilbenoids to reduce the generation of reactive oxygen species and oxidative free radicals. This invention relates to the use Dendrobium-derived extracts or ingredients or stilbenoids in the formulation of skin-protection, skin-whitening and/or anti-skin aging products.

  本发明涉及一种皮肤保护组合物，该组合物包含从铁皮石斛植物（如Dendrobium officinale和Dendrobium nobile）中提取的类石斛素和/或含类石斛素的提取物，用于控制黑色素生成、皮肤变黑和皮肤老化。更具体地说，它涉及使用石斛成分和石斛素来减少黑色素细胞中黑色素的形成。本发明还涉及使用铁皮石斛成分和类石斛烯减少活性氧和氧化自由基的生成。本发明涉及在皮肤保护、皮肤美白和/或抗衰老产品配方中使用铁皮石斛提取物或成分或类石斛素。
• Method of using of dihydro-resveratrol or its stilbenoid derivatives and/or chemical variants as antimicrobial agents
  申请人：Hong Kong Baptist University

  公开号：US10351500B2

  公开（公告）日：2019-07-16

  The present invention relates to a composition for preventing or reducing microbial growth, particularly the growth of dermatophytic fungi, and/or aciduric and acidogenic gram-positive bacteria. More particularly, it relates to the use of trans-3,5,4′-trihydroxybibenzyl, also known as dihydro-resveratrol, or its dihydrostilbene derivatives and/or chemical variants as an anti-microbial agent. The present invention further relates to the management of dermatophytosis often caused by dermatophytic fungi and the management of dental caries often mediated by aciduric and acidogenic gram-positive Streptococci. The present invention therefore has applications in preventing, alleviating and/or treating dermatophytosis and dental caries.

  本发明涉及一种用于防止或减少微生物生长的组合物，特别是皮癣真菌和/或酸性和酸性革兰氏阳性菌的生长。更具体地说，它涉及反式-3,5,4′-三羟基白藜芦醇（又称二氢白藜芦醇）或其二氢芪衍生物和/或化学变体作为抗微生物剂的用途。本发明还涉及通常由皮真菌引起的皮癣病的治疗，以及通常由酸性和产酸性革兰氏阳性链球菌介导的龋齿的治疗。因此，本发明可用于预防、缓解和/或治疗皮癣病和龋齿。
• Talvitie, Antti; Mannila, Erkki; Kolehmainen, Erkki, Liebigs Annalen der Chemie, 1992, # 4, p. 399 - 402
  作者：Talvitie, Antti、Mannila, Erkki、Kolehmainen, Erkki

  DOI：——

  日期：——