(E)-2-hydroxy-4,4'-dimethoxychalcone | 24533-03-7

• 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: (E)-2-hydroxy-4,4'-dimethoxychalcone
• 英文别名: 2-hydroxy-4,4'-dimethoxychalcone；(E)-3-(2-hydroxy-4-methoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 24533-03-7
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: MAWLQXMNFZTBAY-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-hydroxy-4,4'-dimethoxychalcone 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 4',7-dimethoxyflavylium perchlorate
  参考文献：
  名称：

  Hydrolysis of Benzopyrylium Dyes - An Application of the Concept of Chemical Hardness

  摘要：

  A systematic study on the relationship between the substitution pattern, the pK(a) values, and spectral properties of flavylium cations and the respective-(CH2)(2)-bridged analoga (5,6-dihydrobenzo[c]xanthylium cations) is given in order to find rules concerning their spectral behaviour and their chemical reactivity.Our results show that the concept of chemical hardness can explain the different reactivity of 4'- and 7'-substituted flavylium ions against HO-. The pK(a) values of these species, which can act as a measure of reactivity with respect to a nucleophile, correlate linearly with the absolute hardness calculated from half the energy gap between the frontier orbitals. Since the longest-wavelength UV/VIS absorption maximum is mainly determined by the HOMO-LUMO transition, an analogous linear correlation is obtained between the spectral 0-0 transition and the pK(a) value. Deviations from these correlations are assumed to be due to steric effects.

  DOI：

  10.1002/prac.199633801142
• 作为产物：
  描述：

  4',7-dimethoxyflavylium chloride 以 水 为溶剂， 生成 (E)-2-hydroxy-4,4'-dimethoxychalcone
  参考文献：
  名称：

  Pina, Fernando; Benedito, Lina; Melo, Maria Joao, Anales de Quimica, 1997, vol. 93, # 2, p. 111 - 118

  摘要：

  DOI：

文献信息

• The Reactions of 2-Phenyl-2<i>H</i>-1-benzopyrans and 2-Phenyl-4<i>H</i>-1-benzopyrans with Lead(IV) Acetate
  作者：Kazu Kurosawa、Katsutoshi Yamaguchi、Yasuyuki Nagata、Hisatake Ohki

  DOI：10.1246/bcsj.53.1769

  日期：1980.6

  7-methoxy-2-phenyl-2H-1-benzopyran and 7-methoxy-2-phenyl-4H-1-benzopyran with lead(IV) acetate gave 2-benzoyl-6-methoxybenzofuran and 6-acetoxy-3-methoxy-6-(3-oxo-3-phenyl-1 -propenyl)-2,4-cyclo-hexadien-1-one. The reactions of 7-methoxy-2-(p-methoxy-phenyl)-2H-1-benzopyran and 7-methoxy-2-(p-methoxyphen-yl)-4H-1-benzopyran with lead(IV) acetate also gave the corresponding benzofuran and cyclohexadienone. The reaction

  7-甲氧基-2-苯基-2H-1-苯并吡喃和7-甲氧基-2-苯基-4H-1-苯并吡喃与乙酸铅（IV）反应得到2-苯甲酰基-6-甲氧基苯并呋喃和6-乙酰氧基-3 -甲氧基-6-(3-oxo-3-phenyl-1 -propenyl)-2,4-cyclo-hexadien-1-one。7-甲氧基-2-(对甲氧基-苯基)-2H-1-苯并吡喃和7-甲氧基-2-(对甲氧基苯基)-4H-1-苯并吡喃与乙酸铅(IV)的反应也得到相应的苯并呋喃和环己二烯酮。讨论了反应途径。
• Aminoarylvinyl-s-triazine compounds and uses thereof
  申请人：Candau Didier

  公开号：US20050008588A1

  公开（公告）日：2005-01-13

  The invention relates to the use of at least one agent for screening out light radiation with a wavelength ranging from 370 to 500 nm as an agent for inhibiting the degradation of endogenous carotenoids present in the skin. The invention is useful for treating skin disorders caused by sunlight (e.g., solar urticaria, actinic dermatitis and pigmentation marks). The invention also relates to novel aminoarylvinyl-s-triazine compounds and to the use thereof as agents for screening out light radiation ranging from 370 to 500 nm.

  本发明涉及使用至少一种筛选出波长范围在370至500纳米的光辐射的剂作为抑制皮肤内源类胡萝卜素降解的剂。本发明可用于治疗由阳光引起的皮肤疾病（例如太阳性荨麻疹、光化性皮炎和色素斑）。本发明还涉及新型氨基芳基乙烯基-s-三嗪化合物及其作为筛选出波长范围在370至500纳米的光辐射的剂的用途。
• AMINOARYLVINYL-S-TRIAZINE COMPOUNDS AND USES THEREOF
  申请人：Candau Didier

  公开号：US20090074820A1

  公开（公告）日：2009-03-19

  The invention relates to the use of at least one agent for screening out light radiation with a wavelength ranging from 370 to 500 nm as an agent for inhibiting the degradation of endogenous carotenoids present in the skin. The invention is useful for treating skin disorders caused by sunlight (e.g., solar urticaria, actinic dermatitis and pigmentation marks). The invention also relates to novel aminoaryl-vinyl-s-triazine compounds and to the use thereof as agents for screening out light radiation ranging from 370 to 500 nm.

  本发明涉及使用至少一种筛选波长在370至500纳米范围内的光辐射的药剂作为抑制皮肤内源类胡萝卜素降解的药剂。本发明对于治疗由阳光引起的皮肤疾病（例如太阳性荨麻疹、光化性皮炎和色素斑）非常有用。本发明还涉及新的氨基芳基乙烯基-s-三嗪化合物及其作为筛选波长在370至500纳米范围内的光辐射的药剂的用途。
• Utilisation d'au moins un filtre de la lumière bleue pour préserver le capital de caroténoides endogènes de la peau; nouveaux filtres de la lumière bleue; compositions cosmétiques
  申请人：L'OREAL

  公开号：EP1484051A2

  公开（公告）日：2004-12-08

  L'invention concerne l'utilisation d'au moins un agent filtrant les radiations lumineuses allant de 370 à 500 nm dans la fabrication d'une composition appliquée sur la surface de la peau comme agent inhibiteur de la dégradation des caroténoides endogènes présents dans la peau. Ladite composition peut être un produit cosmétique destiné à la protection du teint de la peau. Elle peut être également un produit cosmétique destiné à la protection naturelle antioxydante de la peau. La composition peut être aussi un produit dermatologique destiné aux traitements des désordres cutanés provoqués par le rayonnement solaire (urticaires solaires, lucite, tâches pigmentaires). L'invention concerne également de nouveaux composés amino aryl vinyl-s-triazine ainsi que leur utilisation en cosmétique comme agent filtrant les radiations lumineuses allant de 370 à 500 nm. L'invention concerne les compositions cosmétiques ou dermatologiques contenant ces composés amino aryl vinyl-s-triazine.

  本发明涉及在制造涂抹于皮肤表面的组合物时，使用至少一种可过滤 370 至 500 纳米光辐射的制剂，作为抑制皮肤中存在的内源性类胡萝卜素降解的制剂。 上述组合物可以是用于保护皮肤肤色的化妆品。它也可以是一种用于皮肤天然抗氧化保护的化妆品。 该组合物也可以是一种皮肤科产品，用于治疗太阳辐射引起的皮肤疾病（日光性荨麻疹、白斑、色素沉着斑）。 本发明还涉及新的氨基芳基乙烯基-s-三嗪化合物及其在化妆品中作为过滤 370 至 500 纳米光辐射剂的用途。 本发明还涉及含有这些氨基芳基乙烯基-s-三嗪化合物的化妆品或皮肤科组合物。
• Ortho effect in the fragmentation of 2-acetoxychalcones under electron impact
  作者：Rolf Mentlein、Erich Vowinkel

  DOI：10.1002/oms.1210190708

  日期：1984.7

  Abstract2‐Acetoxychalcones decompose under electron impact conditions by loss of an acetoxy fragment to form flavylium ions. The effect is restricted to the ortho position and is reduced after hydrogenation of the chalcone double bond. The intense flavylium ion originates—as shown by specific labelling with 18O—from two different fragmentation lines: (a) direct loss of an acetoxy radical by cleavage of the phenolic ArO bond and (b) sequential elimination of ketene and a hydroxy radical.