5-[(3,4-二羟基苯基)甲基]二氢-2(3H)-呋喃酮 | 21618-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 5-[(3,4-二羟基苯基)甲基]二氢-2(3H)-呋喃酮
• 中文别名: 5-[(3,4-二羟基苯基)甲基]噁烷-2-酮
• 英文名称: (+/-)-5-(3,4-Dihydroxy-benzyl)-dihydro-furan-2-on
• 英文别名: (-)-5-(3',4'-Dihydroxyphenyl)-γ-valerolactone；δ-(3,4-dihydroxyphenyl)-γ-valerolactone；5-(3′,4′-dihydroxyphenyl)-γ-valerolactone；5-[(3,4-Dihydroxyphenyl)methyl]oxolan-2-one
• CAS: 21618-92-8
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

物化性质

• 熔点：
  145-146℃
• 沸点：
  468.4±25.0 °C(Predicted)
• 密度：
  1.375
• 溶解度：
  DMF：10 mg/ml，DMSO：10 mg/ml，乙醇：微溶，PBS（pH 7.2）：0.25 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

ADMET

代谢

5-(3',4'-二羟基苯基)-γ-戊内酯是表儿茶素的已知人体代谢物。

5-(3',4'-dihydroxyphenyl)-gamma-valerolactone is a known human metabolite of Epicatechin.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  5-[(3,4-二羟基苯基)甲基]二氢-2(3H)-呋喃酮 在 氨 作用下， 生成 (Ξ)-5-(3,4-dihydroxy-phenyl)-4-hydroxy-valeric acid amide
  参考文献：
  名称：

  Watanabe, Journal of the Agricultural Chemical Society of Japan, 1959, vol. 23, p. 257

  摘要：

  DOI：
• 作为产物：
  描述：

  4-戊烯酸甲酯 在 palladium diacetate 、 氢氧化钾 、 三溴化硼 、 copper(II) sulfate 、 三苯基膦 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 生成 5-[(3,4-二羟基苯基)甲基]二氢-2(3H)-呋喃酮
  参考文献：
  名称：

  Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives

  摘要：

  Syntheses are reported for metabolites M4 (1) and M6 (2) of the green tea polyphenols epicatechin (EC) and epigallocatechin (EGC) and their gallate derivatives. Several methoxy-derivatives of 1 and 2 were also prepared. Compounds 1 and 2 were evaluated for growth inhibitory activity against a panel of immortalized and malignant human cell lines with 1 being the more active compound. The possible antiinflammatory activity of 1 and its trimethoxy derivative was also evaluated. Neither compound inhibited the release of arachidonic acid, although 1 inhibited NO production by 50% at 20 muM. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.070

文献信息

• COMPOSITION FOR PREVENTING, IMPROVING OR TREATING PHOTOAGING OF SKIN COMPRISING DHPV
  申请人：SUNGKWANG MEDICAL FOUNDATION

  公开号：US20190021976A1

  公开（公告）日：2019-01-24

  The present invention relates to a photoaging inhibitor, and more specifically it relates to a pharmaceutical composition, a food composition or a cosmetic composition for preventing, improving or treating photoaging of skin, comprising DHPV (5-(3′,4′-Dihydroxyphenyl)-Γ-valerolactone) which is a metabolite of cacao. Since DHPV, an active ingredient comprised in the composition according to the present invention is a metabolite of cacao which is a botanical raw material harmless to human body and is not only excellent in biosafety, but also regulates expression of proteins related to skin aging epigenetically, thereby exhibiting an excellent skin aging-preventing function at a low concentration of 1 nM based on skin cells, the composition comprising the same is excellent in use as medicines, cosmetics and foods for preventing, improving and treating skin aging.

  本发明涉及一种抗光老化剂，更具体地涉及一种用于预防、改善或治疗皮肤光老化的药物组合物、食品组合物或化妆品组合物，包括可可的代谢产物DHPV（5-（3′，4′-二羟基苯基）-Γ-戊内酯）。由于DHPV是本发明中组合物中所含的活性成分，它是可可的代谢产物，可可是一种对人体无害的植物原料，不仅在生物安全性方面表现出色，而且通过表观遗传调节皮肤老化相关的蛋白质的表达，从而在基于皮肤细胞的低浓度1 nM下表现出优异的皮肤抗老化功能，因此，包含相同成分的组合物在预防、改善和治疗皮肤老化方面用作药物、化妆品和食品方面非常出色。
• DHPV의 신규한 합성방법
  申请人：SUNGKWANG MEDICAL FOUNDATION 의료법인 성광의료재단(219950157551) BRN ▼220-82-01517

  公开号：KR102003033B1

  公开（公告）日：2019-07-23

  본 발명은 DHPV의 신규한 합성방법에 관한 것으로, 보다 상세하게는 카카오 주요 대사산물인 DHPV(5-3',4'-Dihydroxyphenyl)-r-valerolactone)의 신규한 합성방법에 관한 것으로, 대량합성이 용이할 뿐만 아니라, 항산화 및 항노화 생리활성을 나타내는 이성질체의 선택이 용이하도록 하다는 장점을 가져, 화장품 및 의약품의 기능성 소재로 높은 가치를 지닐 수 있는 DHPV를 간단하고 경제적으로 대량 생산할 수 있게 한다는 효과를 갖는다.

  这项发明涉及一种新的DHPV合成方法，更详细地说，涉及一种新的合成方法，用于Kakao的主要代谢产物DHPV（5-3'，4'-Dihydroxyphenyl）-r-valerolactone的合成。该方法具有易于大规模合成的优点，使得选择表现出抗氧化和抗衰老生理活性的同分异构体更加容易，从而使DHPV成为具有高价值的功能性化妆品和药物原料，同时实现了简单经济地大规模生产DHPV的效果。
• Concise Synthesis of Catechin Metabolites 5-(3′,4′-Dihydroxyphenyl)-γ-valerolactones (DHPV) in Optically Pure Form and Their Stereochemical Effects on Skin Wrinkle-Reducing Activities
  作者：Joonseong Hur、A-Ram Kim、Hyun Su Kim、Changjin Lim、Taewoo Kim、Tae-Aug Kim、Jaehoon Sim、Young-Ger Suh

  DOI：10.3390/molecules25081970

  日期：——

  A concise and scalable synthetic route for optically pure (4S) and (4R)-5-(3′,4′-dihydroxyphenyl)-γ-valerolactones (DHPVs), catechin metabolites, has been developed via the efficient construction of a γ-valerolactone moiety from hexenol. Noticeably, the different skin wrinkle-reducing activities of each metabolite were revealed via our unique syntheses of DHPVs in an enantiomerically pure form.

  通过有效构建 γ- 代谢物，开发了一种简洁且可扩展的光学纯 (4S) 和 (4R)-5-(3',4'-二羟基苯基)-γ-戊内酯 (DHPV) 代谢物合成路线。来自己烯醇的戊内酯部分。值得注意的是，通过我们独特的对映异构纯形式的 DHPV 的合成，揭示了每种代谢物的不同皮肤皱纹减少活性。
• Concise Synthesis of Ring-Fission Metabolites of Epicatechin: 5-(3,4-Dihydroxybenzyl)dihydrofuran-2(3<i>H</i>)-one M6
  作者：Xiaowei Chang、Weimin Peng、Yin-Fang Yao、Jan Koek

  DOI：10.1080/00397910903419845

  日期：2010.10.20

  The ring-fission metabolites of epicatechin, 5-(3,4-dihydroxybenzyl)dihydrofuran-2(3H)-one M6 and 3-methylated M6, were prepared from 3,4-dihydroxybenzaldehyde and furan-2(5H)-one using two new concise methods in excellent yields (three or two steps in 40–60% overall yield).

  表儿茶素、5-(3,4-二羟基苄基)二氢呋喃-2(3H)-one M6 和 3-甲基化 M6 的裂环代谢物是由 3,4-二羟基苯甲醛和呋喃-2(5H)-one 制备的两种新的简洁方法，产量极佳（三到两步，总产量为 40-60%）。
• Glycan therapeutics and related methods thereof
  申请人：KALEIDO BIOSCIENCES, INC.

  公开号：US10314853B2

  公开（公告）日：2019-06-11

  Preparations of glycan therapeutics, pharmaceutical compositions and medical foods thereof, optionally comprising micronutrients, polyphenols, prebiotics, probiotics, or other agents are provided and methods of making same. Also provided are methods of using said gycan therapeutics, e.g. for the modulation of human gastrointestinal microbiota and to treat dysbioses.

  本发明提供了可选择包含微量营养素、多酚、益生元、益生菌或其他制剂的聚糖疗法制剂、药物组合物及其医用食品，以及制造方法。还提供了使用所述糖治疗剂的方法，例如用于调节人类胃肠道微生物群和治疗菌群失调。