3-hydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one | 92439-38-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-hydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
• 英文别名: 4H-1-Benzopyran-4-one, 3-hydroxy-2-(3,4,5-trihydroxyphenyl)-；3-hydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
• CAS: 92439-38-8
• 化学式: C₁₅H₁₀O₆
• 分子量: 286.241
• InChiKey: FBWPKKNAKFWYOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4,5-三苄氧基苯甲酸 在 咪唑 、 4-二甲氨基吡啶 、 氯化亚砜 、 10% palladium hydroxide on charcoal 、 四丁基氟化铵 、 氢气 、 二甲基二环氧乙烷 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 88.0h， 生成 3-hydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthetic Studies of Fisetin, Myricetin and Nobiletin Analogs and Related Probe Molecules

  摘要：

  DOI：

  10.3987/com-13-s(s)107

文献信息

• [EN] FLAVONOID COMPOUNDS AS THERAPEUTIC ANTIOXIDANTS<br/>[FR] COMPOSES FLAVONOIDES EN TANT QU'ANTIOXYDANTS THERAPEUTIQUES
  申请人：ROWETT RES INST

  公开号：WO2004007475A1

  公开（公告）日：2004-01-22

  Novel flavonoid compounds having anti-oxidant activity are described. Formula (1). The compounds have been shown to exhibit anti-oxidative properties in biological systems and their utility in a sunscreen or skincare composition or to treat conditions involving oxidative damage, especially curative or prophylactic treatment of Alzheimer's disease or ischaemia-reperfusion and injury, is described.

  描述了具有抗氧化活性的新型黄酮类化合物。公式（1）。已经证明这些化合物在生物系统中展现出抗氧化特性，其在防晒霜或护肤品中的用途，或用于治疗涉及氧化损伤的情况，特别是治疗或预防治疗阿尔茨海默病或缺血再灌注和损伤的情况。
• Flavonoid compounds as therapeutic antioxidants
  申请人：Caldwell Thomas Stuart

  公开号：US20060137207A1

  公开（公告）日：2006-06-29

  Novel flavonoid compounds having anti-oxidant activity are described. Formula 1. The compounds have been shown to exhibit anti-oxidative properties in biological systems and their utility in a sunscreen or skincare composition or to treat conditions involving oxidative damage, especially curative or prophylactic treatment of Alzheimer's disease or ischaemia-reperfusion injury, is described.

  描述了具有抗氧化活性的新型黄酮类化合物。公式1。已经证明这些化合物在生物系统中表现出抗氧化性质，并描述了它们在防晒霜或护肤组合物中的实用性，或用于治疗涉及氧化损伤的疾病，特别是治疗阿尔茨海默病或缺血再灌注损伤的治疗或预防。
• Compositions and methods for promoting weight loss, thermogenesis, appetite suppression, lean muscle mass, increasing metabolism and boosting energy levels, and use as a dietary supplement in mammals
  申请人：——

  公开号：US20040077556A1

  公开（公告）日：2004-04-22

  The invention is both a composition and a method for promoting weight loss in mammals, for promoting thermogenesis in mammals, for increasing metabolism and boosting energy levels in mammals, promoting appetite suppression in mammals, for promoting lean muscle mass in mammals and for a diet supplement. The primary mechanism of action for the invention is that it increases norepinephrine levels, which promotes a rise in metabolism, thus leading to more calories burned and more energy expended primarily through the burning or metabolism of adipose tissue (fat) through lipolysis, without the destruction or metabolism of muscle tissue. The present invention relates to a nutritional supplement composition, and the methods for the administration thereof, comprising of (1) an effective amount of epigallocatechin gallate (EGCG), the chemical name of which has been described as ((2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate), and (2) various other substances (singly or in any combination thereof), which either (a) inhibit cyclic adenosine monophosphate (cAMP) phosphodiesterase, (b) stimulate lipolysis, (c) stimulate thermogenesis (i.e., increase metabolism) (d) and/or increase norepinephrine levels, or (e) any combination thereof. In a preferred embodiment, the basic invention is a composition, and a method for the administration thereof, comprising effective amounts of epigallocatechin gallate, caffeine, and l-tyrosine.

  本发明既是一种组合物，也是一种方法，可用于促进哺乳动物减肥、促进哺乳动物产热、提高哺乳动物的新陈代谢和能量水平、促进哺乳动物食欲抑制、促进哺乳动物瘦肌肉质量，也是一种饮食补充剂。本发明的主要作用机理是提高去甲肾上腺素水平，促进新陈代谢，从而主要通过脂肪分解燃烧或代谢脂肪组织（脂肪）来消耗更多卡路里和更多能量，而不破坏或代谢肌肉组织。 本发明涉及一种营养补充剂组合物及其施用方法，该组合物包括（1）有效量的表没食子儿茶素没食子酸酯（EGCG），其化学名称已被描述为（(2R,3R)-2-(3,4,5-三羟基苯基)-3,4-二氢-1&lsqb；2H]-苯并吡喃-3,5,7-三醇 3-(3,4,5-三羟基苯甲酸酯)，以及 (2) 其他各种物质（单独使用或任意组合使用），这些物质(a) 可抑制环磷酸腺苷（cAMP）磷酸二酯酶，(b) 可刺激脂肪分解，(c) 可刺激产热（即 "产热"）。e.,(d) 和/或增加去甲肾上腺素水平，或 (e) 以上任何组合。 在一个优选的实施方案中，本发明是一种组合物及其施用方法，其中包含有效量的表没食子儿茶素没食子酸酯、咖啡因和 l-酪氨酸。
• Synthesis and biological evaluation of novel flavonols as potential anti-prostate cancer agents
  作者：Robert G. Britton、Emma Horner-Glister、Odette A. Pomenya、Ewan E. Smith、Roanne Denton、Paul R. Jenkins、William P. Steward、Karen Brown、Andreas Gescher、Stewart Sale

  DOI：10.1016/j.ejmech.2012.06.031

  日期：2012.8

  A library of flavonol analogues was synthesised and evaluated as potential anticancer agents against a human prostate cancer cell line, 22rv1. Compounds 3, 8 and 11 (IC50 2.6, 3.3 and 4.0 mu M respectively) showed potent cancer cell growth inhibition, comparable to the lead compound 3',4',5'-trimethoxyflavonol (1) (IC50 3.1 mu M) and superior to the naturally occurring flavonols quercetin (16) and fisetin (22) (both >15 mu M). Results indicate that the 3',4',5'- arrangement of either hydroxy (OH) or methoxy (OMe) residues is important for growth arrest of these cells and that the OMe analogues may be superior to their OH counterparts. Compounds 1, 3, 8 and 11 warrant further investigation as potential agents for the management of prostate cancer. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Effect of Flavonol Derivatives on the Carrageenin-Induced Paw Edema in the Rat and Inhibition of Cyclooxygenase-1 and 5-Lipoxygenasein Vitro
  作者：Andrea M. Sobottka、Wolfgang Werner、Gottfried Blaschke、Werner Kiefer、Ulrike Nowe、Gerd Dannhardt、Elfrides E. S. Schapoval、Eloir P. Schenkel、Gerhard K.E. Scriba

  DOI：10.1002/1521-4184(20007)333:7<205::aid-ardp205>3.0.co;2-y

  日期：2000.7

  Alkoxyflavonols were synthesized by the Algar-Flynn-Oyamada (AFO) cyclization of chalcones. Hydroxyflavonols were prepared by dealkylation of methoxyflavonols by refluxing in hydroiodic acid. The alkoxyflavonols 3-hydroxy-2-(2,3,4-trimethoxyphenyl)-4H-chromen-4-one (6), 2-(4-ethoxyphenyl)-3-hydroxy-4H-chromen-4-one (7), 2-(4-butoxyphenyl)-3-hydroxy-4H-chromen-4-one (10), and 2-(3-n-butoxyphenyl)-3-hydroxy-4H-chromen-4-one (11) as well as the trihydroxy derivative 3-hydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one (18) displayed high anti-inflammatory activity in carrageenin-induced rat paw edema. Additionally, the inhibition of enzymes of the arachidonic acid cascade by the derivatives was investigated in vitro. In contrast to the natural compound quercetin, the compounds were more potent inhibiting cyclooxygenase-1 than 5-lipoxygenase except for 3-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one (5). No correlation between the anti-inflammatory activity in the rat paw edema test and the inhibition of 5-lipoxygenase or cyclooxygenase-1 could be observed. In conclusion, the present results suggest that other effects than inhibition of these enzymes of the arachidonic acid cascade are important for the anti-inflammatory activity of the investigated alkoxyflavonols.