3',5'-二甲氧基-4'-羟基-(2-羟基)苯乙酮 | 90426-22-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3',5'-二甲氧基-4'-羟基-(2-羟基)苯乙酮
• 中文别名: L-半胱氨酸,甘氨酰-L-精氨酰甘氨酰-L-a-门冬氨酰-L-丝氨酰-
• 英文名称: 3',5'-dimethoxy-4'-hydroxy-(2-hydroxy)acetophenone
• 英文别名: 2,4'-dihydroxy-3',5'-dimethoxyacetophenone；α-Hydroxyacetosyringone；hydroxyacetosiringone；danielone；2-hydroxy-1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone；2-Hydroxy-1-(4-hydroxy-3,5-dimethoxy-phenyl)-aethanon；2-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone
• CAS: 90426-22-5
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: ZTBAPEIDNUHRNC-UHFFFAOYSA-N

物化性质

• 熔点：
  145°C
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3',5'-二甲氧基-4'-羟基-(2-羟基)苯乙酮 、 2,4-二羟基苯甲醛 在 盐酸 、 乙酸乙酯 作用下， 生成 3,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)-chromenylium; chloride
  参考文献：
  名称：

  Grove et al., Journal of the Chemical Society, 1934, p. 1614,1615

  摘要：

  DOI：
• 作为产物：
  描述：

  4'-O-benzyl-α-hydroxyacetosyringone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以95%的产率得到3',5'-二甲氧基-4'-羟基-(2-羟基)苯乙酮
  参考文献：
  名称：

  Synthesis of α-Hydroxyacetosyringone

  摘要：

  从木瓜果实中提取的一种植物皂苷经四个步骤合成；这一过程涉及一种普默尔（Pummerer）型反应。

  DOI：

  10.3390/51201287

文献信息

• New Phototriggers:¹ Extending the <i>p</i>-Hydroxyphenacyl π−π* Absorption Range
  作者：Peter G. Conrad、Richard S. Givens、Jörg F. W. Weber、Karl Kandler

  DOI：10.1021/ol005856n

  日期：2000.6.1

  [equation--see text] Introducing 3-methoxy or 3,5-dimethoxy substituents on the 4-hydroxyphenacyl (pHP) photoremovable protecting group has been explored with two excitatory gamma-amino acids, L-glutamic acid and gamma-amino butyric acid (GABA). These substituents significantly extend the absorption range of the pHP chromophore, e.g., the tail of absorption bands of 2a,b extend above 400 nm, well beyond

  [等式-见正文]已经研究了用两种兴奋性γ-氨基酸（L-谷氨酸和γ-氨基丁酸）在4-羟基苯甲酰基（pHP）可光除去的保护基上引入3-甲氧基或3,5-二甲氧基取代基的方法。 （GABA）。这些取代基显着扩展了pHP发色团的吸收范围，例如2a，b的吸收带的尾部延伸超过400 nm，远远超出了芳香族氨基酸和核苷酸的吸收。辐照释放出氨基酸的速率常数约为10（7）s（-）（1），外观效率（Phi（app））为0.03-0.04。光产物是通过pHP激发三重态形成的，主要是光还原和光水解的产物。1a，b也重新排列为苯乙酸3。
• NOVEL BENZAMIDE DERIVATIVE AND USE THEREOF
  申请人：VIVOZON, INC.

  公开号：US20140336378A1

  公开（公告）日：2014-11-13

  Disclosed are a novel benzamide derivative and pharmaceutical use thereof, and more particularly, a novel benzamide derivative having a structure of Formula 1 or pharmaceutically acceptable salts thereof, and a composition for prevention or treatment of pain or itching including the above material. The novel benzamide derivative and pharmaceutically acceptable salt thereof according to the present invention exhibit excellent pain-suppressive effect and, in particular, pain-suppressive effect in not only a neuropathic animal model but also other models such as a formalin model, and therefore, may be used in suppression of different pains such as nociceptive pain, chronic pain, etc. Further, since it was demonstrated that the present invention displays anti-pruritic efficacy even in an itching model, to which a mechanism and treatment concept established with respect to pain is applied, the present invention may also be effectively used in radical treatment of atopic dermatitis by applying the inventive product to an anti-pruritic composition in order to suppress an initial itching stage and treat symptoms thereof, thus preventing skin damage or inflammation after the scratching stage.

  揭示了一种新的苯甲酰胺衍生物及其药用，更具体地说，一种具有化学式1结构或其药用盐的新苯甲酰胺衍生物，以及包括上述材料的用于预防或治疗疼痛或瘙痒的组合物。根据本发明，所述新的苯甲酰胺衍生物及其药用盐表现出优异的镇痛效果，特别是在不仅神经病理动物模型中而且其他模型如福尔马林模型中表现出的镇痛效果，因此，可用于抑制不同类型的疼痛，如伤害性疼痛、慢性疼痛等。此外，由于证明了本发明在瘙痒模型中显示出抗瘙痒功效，应用于疼痛方面建立的机制和治疗概念，因此，本发明还可通过将创新产品应用于抗瘙痒组合物中，以抑制初始瘙痒阶段并治疗其症状，从而预防刮痒阶段后的皮肤损伤或炎症。
• Identification of Plant Factors Inducing Virulence Gene Expression in Agrobacterium tumefaciens.
  作者：Yan-Nong SONG、Masaaki SHIBUYA、Yutaka EBIZUKA、Ushio SANKAWA

  DOI：10.1248/cpb.39.2347

  日期：——

  In the natural gene-transfer system of Agrobacterium tumefaciens, the expression of virulence (vir) gene of Ti (tumor inducing) plasmid is essential for the subsequent transferred deoxyribonucleic acid (T-DNA) transfer from bacterium to plant cells. vir gene expression is induced by signal compounds from pants such as acetosyringone and α-hydroxyacetosyringone which were isolated from hairy root cultures of Nicotiana tabacum. In a search for intrinsic signal compounds in plants, acetosyringone and α-hydroxyacetosyringone were identified as the vir-inducing compounds of the hairy root cultures of Atropa belladonna. The signal compounds of seedlings of Pisum sativum were identified as sinapyl and coniferyl alcohols. The quantities of these vir-inducing compounds were significantly increased when plant tissues were wounded, though the degree of increase was markedly different in each plant.

  在农杆菌（Agrobaacterium tumefaciens）的天然基因转移系统中，Ti（肿瘤诱导）质粒的毒力（vir）基因的表达对于随后的脱氧核糖核酸（T-DNA）从细菌转移到植物细胞至关重要。vir 基因的表达受到来自裤子的信号化合物的诱导，如从烟草（Nicotiana tabacum）毛状根培养物中分离出的乙酰丁香酮（acetosyringone）和α-羟基乙酰丁香酮（α-hydroxyacetosyringone）。在寻找植物内在信号化合物的过程中，发现乙酰丁香酮和α-羟基乙酰丁香酮是颠茄毛根培养物中的病毒诱导化合物。经鉴定，野豌豆幼苗的信号化合物为山奈醇和针叶醇。当植物组织受伤时，这些病毒诱导化合物的数量明显增加，但每种植物的增加程度明显不同。
• Synthesis of Danielone (α-Hydroxyacetosyringone)
  作者：Javier G. Luis、Lucía S. Andrés

  DOI：10.1039/a808061e

  日期：——

  An efficient simple three step synthesis of the phytoalexin danielone (α-hydroxyacetosyringone) from acetosyringone is described.

  本研究描述了从乙酰丁香酮高效、简单地分三步合成植物雌激素达尼尔酮（δ-羟基乙酰丁香酮）的过程。
• Synthesis of the Main Red Wine Anthocyanin Metabolite: Malvidin-3-O-β-Glucuronide
  作者：Luís Cruz、Iva Fernandes、Ana Évora、Victor de Freitas、Nuno Mateus

  DOI：10.1055/s-0036-1588673

  日期：——

  malvidin-3-O-β-glucuronide, with the main MS2 and MS3 fragments corresponding to the loss of glucuronic moiety [M – 176]+ m/z = 331 and methyl groups [M – 176 – 16]+ m/z = 315. The configuration and the position of the linkage between the aglycone and the glucuronyl residue was confirmed by NMR spectroscopy, considering the coupling constant between H-C1′′ and H-C2′′ and HMBC/NOESY connectivities.

  花青素在人类中被广泛食用，尽管它们对健康有影响，但它们的血浆浓度似乎很低。这在很大程度上归因于缺乏标准，无法充分确定检测到的化合物的身份，而这些化合物通常不是原始来源中存在的化合物。在这项工作中，开发了红酒中存在的主要花青素的一种葡萄糖醛酸结合物的化学合成策略。通过 HPLC-DAD、LC-MS 和 NMR 光谱检查代谢物的纯度和身份。经证实，获得的化合物是malvidin-3-O-β-glucuronide，主要的MS2和MS3片段对应于葡糖醛酸部分的损失[M – 176]+ m/z = 331和甲基[M – 176 – 16]+ m/z = 315。