2',3,4'-trihydroxy-4-methoxydihydrochalcone | 50297-39-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2',3,4'-trihydroxy-4-methoxydihydrochalcone
• 英文别名: 1-(2,4-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)-propan-1-one；1-(2,4-Dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
• CAS: 50297-39-7
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: GCOFCBCRRXZXNC-UHFFFAOYSA-N

物化性质

• LogP：
  2.876 (est)
• 物理描述：
  Pearly white powder; Bland aroma
• 溶解度：
  Practically insoluble to insoluble

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 五甲基苯 、 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 以74 %的产率得到2',3,4'-trihydroxy-4-methoxydihydrochalcone
  参考文献：
  名称：

  含有二氢查尔酮作为酪氨酸酶抑制剂治疗皮肤色素沉着过度的新型杂化物的设计、合成和生物学评价

  摘要：

  黑色素沉积过多可能会导致一系列的皮肤病。黑色素的产生是由黑色素细胞进行的，其中酪氨酸酶起着关键作用。在这项工作中，我们鉴定了一系列具有二氢查耳酮骨架和间苯二酚结构的新型酪氨酸酶抑制剂杂化物，它们可以抑制酪氨酸酶活性并减少皮肤中的黑色素含量。化合物11c具有最强的抗酪氨酸酶活性，在纳摩尔浓度范围内显示出 IC 50值，同时具有显着的抗氧化活性和低细胞毒性。此外，在 HPLC 分析和 3D OrbiSIMS 成像可视化支持下的体外渗透测试表明11c具有出色的渗透性. 更重要的是，化合物11c在体内的豚鼠模型中减少了紫外线诱导的皮肤色素沉着中的黑色素含量。这些结果表明，化合物11c可以作为一种很有前途的强效酪氨酸酶抑制剂，用于开发治疗皮肤色素沉着过度的潜在疗法。

  DOI：

  10.1021/acs.jmedchem.3c00012

文献信息

• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。
• Identification of Interleukin-8-Reducing Lead Compounds Based on SAR Studies on Dihydrochalcone-Related Compounds in Human Gingival Fibroblasts (HGF-1 cells) In Vitro
  作者：Katharina Schueller、Joachim Hans、Stefanie Pfeiffer、Jessica Walker、Jakob P. Ley、Veronika Somoza

  DOI：10.3390/molecules25061382

  日期：——

  Background: In order to identify potential activities against periodontal diseases, eighteen dihydrochalcones and structurally related compounds were tested in an established biological in vitro cell model of periodontal inflammation using human gingival fibroblasts (HGF-1 cells). Methods: Subsequently to co-incubation of HGF-1 cells with a bacterial endotoxin (Porphyromonas gingivalis lipopolysaccharide, pgLPS) and each individual dihydrochalcone in a concentration range of 1 µM to 100 µM, gene expression of interleukin-8 (IL-8) was determined by qPCR and cellular interleukin-8 (IL-8) release by ELISA. Results: Structure–activity analysis based on the dihydrochalcone backbone and various substitution patterns at its aromatic ring revealed moieties 2′,4,4′,6′-tetrahydroxy 3-methoxydihydrochalcone (7) to be the most effective anti-inflammatory compound, reducing the pgLPS-induced IL-8 release concentration between 1 µM and 100 µM up to 94%. In general, a 2,4,6-trihydroxy substitution at the A-ring and concomitant vanilloyl (4-hydroxy-3-methoxy) pattern at the B-ring revealed to be preferable for IL-8 release inhibition. Furthermore, the introduction of an electronegative atom in the A,B-linker chain led to an increased anti-inflammatory activity, shown by the potency of 4-hydroxybenzoic acid N-vanillylamide (13). Conclusions: Our data may be feasible to be used for further lead structure designs for the development of potent anti-inflammatory additives in oral care products.

  背景：为了识别针对牙周疾病的潜在活性，对十八种二氢黄酮类化合物及结构相关化合物在已建立的人牙龈成纤维细胞（HGF-1细胞）牙周炎生物体外细胞模型中进行了测试。方法：在HGF-1细胞与一种细菌内毒素（牙龈脓毒素脂多糖，pgLPS）和每种单独的二氢黄酮类化合物在1 µM至100 µM浓度范围内共同孵育后，通过qPCR测定白细胞介素-8（IL-8）的基因表达，并通过ELISA测定细胞白细胞介素-8（IL-8）的释放。结果：基于二氢黄酮骨架和其芳香环上的各种取代模式的结构-活性分析显示，2′,4,4′,6′-四羟基-3-甲氧基二氢黄酮（7）是最有效的抗炎化合物，将pgLPS诱导的IL-8释放浓度在1 µM至100 µM之间降低了94%。一般来说，A环上的2,4,6-三羟基取代和B环上的香草酰（4-羟基-3-甲氧基）模式同时出现，对于IL-8释放抑制是首选。此外，在A、B连接链中引入一个电负原子导致了抗炎活性的增加，表现为对4-羟基苯甲酸N-香草酰胺（13）的效力。结论：我们的数据可能可用于进一步设计用于口腔护理产品中强效抗炎添加剂的先导结构。
• COMPOUNDS USEFUL AS MODULATORS OF TRPM8
  申请人：Senomyx, Inc.

  公开号：US20170096418A1

  公开（公告）日：2017-04-06

  The present disclosure relates to compounds which are useful as cooling sensation compounds.

  本公开涉及作为冷感化合物有用的化合物。
• USE OF 1-(2,4-DIHYDROXY-PHENYL)-3-(3-HYDROXY-4-METHOXY-PHENYL)-PROPAN-1-ONE
  申请人：Backes Michael

  公开号：US20110189108A1

  公开（公告）日：2011-08-04

  The invention concerns the use of a deoxy hesperetin dihydrochalcone or a salt of the deoxy hesperetin dihydrochalcone (I) or a mixture comprising or consisting of a plurality of salts of the deoxy hesperetin dihydrochalcone (I) or a mixture comprising or consisting of deoxy hesperetin dihydrochalcone (I) and a salt or a plurality of salts of the deoxy hesperetin dihydrochalcone (I), to influence the strength of taste impressions of sweet-tasting, unpleasant-, in particular bitter-, tasting or both sweet- and unpleasant-, in particular bitter-, tasting substances or mixtures of substances.

  本发明涉及使用脱氧异柚皮素二氢黄酮或脱氧异柚皮素二氢黄酮的盐（I），或包含或由多种脱氧异柚皮素二氢黄酮（I）的盐组成或构成的混合物，或包含或由脱氧异柚皮素二氢黄酮（I）和脱氧异柚皮素二氢黄酮（I）的一个或多个盐组成或构成的混合物，来影响甜味、不愉快-尤其是苦味-或同时甜味和不愉快-尤其是苦味-的物质或物质混合物的味道强度。
• Method for Biotechnological Production of Dihydrochalcones
  申请人：Symrise AG

  公开号：US20140045233A1

  公开（公告）日：2014-02-13

  A method for production of a dihydrochalcone, especially of phloretin, using a transgenic microorganism, containing a nucleic acid section (a), comprising or consisting of a gene coding for a bacterial chalcone isomerase, and/or a nucleic acid section (a′), comprising or consisting of a gene coding for a plant chalcone isomerase, and a nucleic acid section (b), comprising or consisting of a gene coding for a bacterial enoate reductase, corresponding transgenic microorganisms, containing a nucleic acid section (a), comprising or consisting of a gene coding for a bacterial chalcone isomerase, and/or a nucleic acid section (a′), comprising or consisting of a gene coding for a plant chalcone isomerase, and/or a nucleic acid section (b), comprising or consisting of a gene coding for a bacterial enoate reductase, and host cells, containing one or more identical or different such vectors.

  一种利用转基因微生物生产二氢黄酮的方法，特别是花瘤素的方法，其中所述转基因微生物包含核酸片段(a)，包括或仅包括编码细菌查尔酮异构酶的基因，和/或核酸片段(a')，包括或仅包括编码植物查尔酮异构酶的基因，以及核酸片段(b)，包括或仅包括编码细菌烯酸还原酶的基因，所述转基因微生物，包含核酸片段(a)，包括或仅包括编码细菌查尔酮异构酶的基因，和/或核酸片段(a')，包括或仅包括编码植物查尔酮异构酶的基因，和/或核酸片段(b)，包括或仅包括编码细菌烯酸还原酶的基因，以及包含一个或多个相同或不同的这样的载体的宿主细胞。