5,8-二羟基-2-(4-羟基苯基)-6,7-二甲氧基-4H-1-苯并吡喃-4-酮 | 98755-25-0

• 物质功能分类: 天然产物 - 黄酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 5,8-二羟基-2-(4-羟基苯基)-6,7-二甲氧基-4H-1-苯并吡喃-4-酮
• 中文别名: Isothymusin;5,8-二羟基-2-(4-羟基苯基)-6,7-二甲氧基-4H-1-苯并吡喃-4-酮
• 英文名称: isothymusin
• 英文别名: 6,7-dimethoxy-5,8,4'-trihydroxyflavone；5,8-dihydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxychromen-4-one
• CAS: 98755-25-0
• 化学式: C₁₇H₁₄O₇
• 分子量: 330.294
• InChiKey: IODGQWWTJYDCLN-UHFFFAOYSA-N

物化性质

• 熔点：
  214-215 °C(Solv: ethyl acetate (141-78-6); methanol (67-56-1))
• 沸点：
  628.9±55.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5,4''-二羟基-6,7,8-三甲氧基黄酮 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 52.0h， 生成 5,8-二羟基-2-(4-羟基苯基)-6,7-二甲氧基-4H-1-苯并吡喃-4-酮
  参考文献：
  名称：

  Tlc, uv and acidic treatment in the differentiation of 5,6- and 5,8-dihydroxyflavones, 3-methoxyflavones and flavonols

  摘要：

  DOI：

  10.1016/s0040-4020(01)91379-1

文献信息

• Synthesis of 5,8-dihydroxy-6,7-dimethoxyflavones and revised structures for some natural flavones
  作者：T Horie

  DOI：10.1016/0031-9422(95)00070-n

  日期：1995.7

  7-trimethoxyflavones were synthesized from 2′,5′-dihydroxy-3′,4′,6′-trimethoxyacetophenone by adapting the selective O -alkylation and dealkylation, and the differentiation between the flavones and their isomeric 6-hydroxyflavones was clarified by 1 H NMR and UV spectra. Four natural flavones proposed as 5,8-dihydroxy-6,7-dimethoxyflavones, must have other structures and three are shown to be the isomeric

  摘要 以 2',5'-二羟基-3',4',6'-三甲氧基苯乙酮为原料，合成了 6 个 5,8-二羟基-6,7-二甲氧基黄酮和 3 个 8-羟基-5,6,7-三甲氧基黄酮。选择性O-烷基化和脱烷基化，黄酮和它们的异构体6-羟基黄酮之间的区别通过 1 H NMR 和紫外光谱得到澄清。四种天然黄酮被提议为 5,8-二羟基-6,7-二甲氧基黄酮，必须具有其他结构，其中三种被证明是异构的 5,7-二羟基-6,8-二甲氧基黄酮。从 Ageratum conyzoides 中分离出的黄酮被正确识别为 8-hydroxy-5,6,7,3',4',5'-六甲氧基黄酮，但从蜡菊中分离出的黄酮的结构被修改为异构体 7 -羟基-5,6,8-三甲氧基黄酮。
• Method for inhibiting cyclooxygenase and inflammation using cyanidin
  申请人：Board of Trustees operating Michigan State University

  公开号：US20010002407A1

  公开（公告）日：2001-05-31

  A method for inhibiting cyclooxygenase enzymes and inflammation in a mammal using a cherry or cherry anthocyanins, bioflavonoids and phenolics is described. In particular a mixture including the anthocyanins, the bioflavonoids and the phenolics is described for this use.

  描述了一种利用樱桃或樱桃花青素、生物类黄酮和酚类物质抑制哺乳动物体内环氧化酶和炎症的方法。特别是一种包括花青素、生物类黄酮和酚类物质的混合物。
• Method for inhibiting cyclooxygenase and inflammation using cherry bioflavonoids
  申请人：Board of Trustees operating Michigan State University

  公开号：US20010020009A1

  公开（公告）日：2001-09-06

  A method for inhibiting cyclooxygenase enzymes and inflammation in a mammal using a cherry or cherry anthocyanins, bioflavonoids and phenolics is described. In particular a mixture including the anthocyanins, the bioflavonoids and the phenolics is described for this use.

  描述了一种利用樱桃或樱桃花青素、生物类黄酮和酚类物质抑制哺乳动物体内环氧化酶和炎症的方法。特别是一种包括花青素、生物类黄酮和酚类物质的混合物。
• Methods and compositions for enhancing collagen and proteoglycan synthesis in the skin
  申请人：Nimni Marcel

  公开号：US20060045926A1

  公开（公告）日：2006-03-02

  A composition for application to the skin can stimulate the in vivo synthesis of collagen and proteoglycans and improve the appearance of the skin, increasing its elasticity and fullness. In general, a composition according to the present invention comprises: (1) an antioxidant compound in a quantity sufficient to enhance collagen synthesis in the skin; (2) an organic penetrant in which the antioxidant compound is soluble in a sufficient quantity that a concentration of the antioxidant compound sufficient to enhance collagen synthesis can be applied topically and penetrate the skin; (3) a mixture of essential amino acids; (4) a supplemental source of sulfur; and (5) a topical pharmaceutically acceptable carrier. The antioxidant compound can be lipoic acid, a lipoic acid analogue or derivative, a bioflavonoid, a constituent of ginkgo, or an isoflavone. The organic penetrant is preferably benzyl alcohol. Other ingredients, such as esters of tocopherol and ascorbic acid, can be included.

  一种用于皮肤的组合物可以刺激胶原蛋白和蛋白多糖的体内合成，改善皮肤外观，增加皮肤的弹性和饱满度。一般来说，根据本发明的组合物包括：(1) 抗氧化剂化合物，其含量足以促进皮肤中胶原蛋白的合成；(2) 有机渗透剂，其中抗氧化剂化合物的溶解度足以使足以促进胶原蛋白合成的抗氧化剂化合物浓度局部使用并渗透皮肤；(3) 必需氨基酸混合物；(4) 硫的补充来源；(5) 局部用药可接受的载体。抗氧化剂化合物可以是硫辛酸、硫辛酸类似物或衍生物、生物类黄酮、银杏成分或异黄酮。有机渗透剂最好是苯甲醇。也可加入其他成分，如生育酚酯和抗坏血酸酯。
• Compositions and methods for treatment of solar damage
  申请人：Nimni Marcel

  公开号：US20060067959A1

  公开（公告）日：2006-03-30

  An improved composition for treatment of the skin comprises: (1) methionine and cysteine in a quantity sufficient to accelerate restoration of the integrity and fullness of the skin; (2) a mixture of essential amino acids in a quantity sufficient to accelerate restoration of the integrity and fullness of the skin, the mixture comprising isoleucine, leucine, lysine, phenylalanine, threonine, tryptophan, valine, histidine, and arginine; (3) at least one antioxidant in a quantity sufficient to accelerate restoration of the integrity and fullness of the skin; (4) at least one cross-linking agent in a quantity sufficient to accelerate restoration of the integrity and fullness of the skin; (5) at least one metallic catalyst in a quantity sufficient to accelerate restoration of the integrity and fullness of the skin; (6) at least one transepidermal delivery agent in a quantity sufficient to promote delivery of the composition to the skin; and (7) a topical pharmaceutically acceptable carrier. The antioxidant can be ascorbic acid. The cross-linking agent can be proanthocyanidin or silybin. The metallic catalyst can be Cu (II) in a suitable cupric salt. The transepidermal delivery agent can be benzyl alcohol.

  一种用于治疗皮肤的改良组合物包括(1) 蛋氨酸和半胱氨酸，其含量足以加速恢复皮肤的完整性和饱满度；(2) 必需氨基酸混合物，其含量足以加速恢复皮肤的完整性和饱满度，该混合物包括异亮氨酸、亮氨酸、赖氨酸、苯丙氨酸、苏氨酸、色氨酸、缬氨酸、组氨酸和精氨酸；(3) 至少一种抗氧化剂，其含量足以加速恢复皮肤的完整性和饱满度；(4) 至少一种交联剂，其用量应足以加速恢复皮肤的完整性和饱满度； (5) 至少一种金属催化剂，其用量应足以加速恢复皮肤的完整性和饱满度； (6) 至少一种经表皮递送剂，其用量应足以促进将组合物递送至皮肤；以及 (7) 外用药学上可接受的载体。抗氧化剂可以是抗坏血酸。交联剂可以是原花青素或水飞蓟宾。金属催化剂可以是合适的铜盐中的铜（II）。经皮给药剂可以是苯甲醇。