(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl octanoate

• 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: (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl octanoate
• 英文别名: 3-O-octanoyl-(-)-epicatechin；3-O-octanoyl-(+)-D-epicatechin；[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chroman-3-yl] octanoate；[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] octanoate
• 化学式: C₂₃H₂₈O₇
• 分子量: 416.471
• InChiKey: FQKHCXJBKHKDGT-FYYLOGMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  表儿茶素 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 生成 (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl octanoate
  参考文献：
  名称：

  US2014/256741

  摘要：

  公开号：

文献信息

• Antimicrobial Activity of 3-<i>O</i>-Acyl-(-)-epicatechin and 3-<i>O</i>-Acyl-(+)-catechin derivatives
  作者：Park, Ki Duk、Park, Yoon Sun、Cho, Sung Jin、Sun, Won Suck、Kim, Sung Han、Jung, Do Hyun、Kim, Jung Han

  DOI：10.1055/s-2004-818923

  日期：2004.3

  compounds, 3- O-acyl-(-)-epicatechins and 3- O-acyl-(+)-catechins possessing various aromatic groups and aliphatic chains of varying length from C4 to C16 for increasing lipophilicity were synthesized and tested for antimicrobial activities against Gram-positive, Gram-negative bacteria and fungi. The (-)-epicatechin and (+)-catechin derivatives comprised of aromatic groups increased activity and derivatives

  作为抗菌促进化合物的探索性研究，3-O-酰基-（-）-表儿茶素和3-O-酰基-（+）-儿茶素具有不同的芳香族基团和从C4到C16的不同长度的脂族链，以增加亲脂性。合成并测试了对革兰氏阳性，革兰氏阴性细菌和真菌的抗菌活性。由芳族基团组成的（-）-表儿茶素和（+）-儿茶素衍生物的活性增强，并且在C8至C10的附近具有碳原子酰基链基的衍生物表现出很强的抗菌活性（MIC = 2-8 microg / ml）抵抗革兰氏阳性细菌，抗真菌活性弱。然而，当取代基的碳链长度太短（C4至C6）或太长（C16）时，活性降低。
• [EN] ANTIMICROBIAL COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSITIONS ANTIMICROBIENNES ET PROCEDES D'UTILISATION
  申请人：STAPLETON PAUL

  公开号：WO2005034976A1

  公开（公告）日：2005-04-21

  A catechin is modified in at least one position (most preferably in the 3-position of the C-ring) to increase its lipophilicity. Contemplated catechins are demonstrated to have significantly improved antibacterial properties, likely due to catastrophic membrane damage.

  一种儿茶素至少在一个位置上进行改变（最好是在C环的3号位置）以增加其亲脂性。考虑到的儿茶素已被证明具有显著改善的抗菌性能，可能是由于破坏细胞膜所致。
• Reversing baldness through follicle regeneration
  申请人：Postrel Richard

  公开号：US11331300B2

  公开（公告）日：2022-05-17

  This invention reverses male pattern baldness by shocking dormant hair follicles out of their androgen induced hibernation phase back to the active hair-growing anagenic phase. The invention integrates two functions: 1) It blocks synthesis of compounds holding the follicles in the telogenic/hibernating phase and 2) It stimulates synthesis of compounds animating the hair-growing/anagenic phase in the follicular activity cycle. One preferred embodiment comprises an enzyme inhibitor blocking the conversion of testosterone to dihydrotestosterone (DHT), a flavonoid simultaneously increasing synthesis of prostaglandins alternative to prostaglandin D2, and a selected cannabinoid compound stimulating restore the hair follicle to its normal growth cycle. This novel trimodal therapy restores the hair follicles to their normal cycling processes and maintains these restorative properties so long as this rebalance in maintained.

  本发明通过将休眠毛囊从雄性激素诱导的冬眠期震回到活跃的头发生长期，从而逆转男性型秃发。本发明集成了两种功能：1）阻止使毛囊处于休止期/冬眠期的化合物的合成；2）刺激毛囊活动周期中使毛发生长期/新生期活跃的化合物的合成。一个优选的实施方案包括：一种酶抑制剂，可阻止睾酮向双氢睾酮（DHT）的转化；一种类黄酮，可同时增加前列腺素 D2 替代物的合成；以及一种精选的大麻素化合物，可刺激毛囊恢复正常的生长周期。这种新颖的三联疗法能使毛囊恢复正常的循环过程，只要保持这种恢复平衡，就能保持这些恢复特性。
• Anticancer activity of 3-O-acyl and alkyl-(−)-epicatechin derivatives
  作者：Ki Duk Park、Sul Gi Lee、Sung Uk Kim、Sung Han Kim、Won Suck Sun、Sung Jin Cho、Do Hyeon Jeong

  DOI：10.1016/j.bmcl.2004.07.063

  日期：2004.10

  By changing the structure or replacing the gallate group of (-)-ECG, 3-O-acyl and alkyl-(-)-epicatechin derivatives were synthesized to be screen as anticancer agents using the MTT assay in vitro against cancer cell lines (PC3, SKOV3, U373MG). 3-O-Acyl and alkyl-(-)-epicatechin derivatives (4-25) exhibited better anticancer activity than (-)-ECG and specially, compounds 6-8, 17-19, which were modified aliphatic chains with moderate sizes (C8-C12) showed strong anticancer activity (IC50 = 6.4-31.2 muM). The introduction of an alkyloxy group on 3-O-hydroxyl instead of an acyloxy group significantly enhanced inhibitory activity. Consequently, the compound that showed the most potency as anticancer agents were 3-O-decyl-(-)-epicatechin (18) (IC50 = 8.9, 7.9, 6.4 muM against PC3, SKOV3, U373MG, respectively), which modified the appropriate lipophilic group on the C-3 hydroxyl as an alkyloxy group. (C) 2004 Elsevier Ltd. All rights reserved.
• EP1849779
  申请人：——

  公开号：——

  公开（公告）日：——