5-(3,5-dihydroxyphenyl)pentanoic acid | 74356-41-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-(3,5-dihydroxyphenyl)pentanoic acid
• 英文别名: 5-(3,5-dihydroxyphenyl)valeric acid；3,5-Dihydroxybenzenepentanoic Acid
• CAS: 74356-41-5
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: QHXNJIMVPAFCPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2918290000

反应信息

• 作为反应物：
  描述：

  5-(3,5-dihydroxyphenyl)pentanoic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以48%的产率得到5-(5-Hydroxypentyl)-1,3-benzenediol
  参考文献：
  名称：

  Discovery of KLS-13019, a Cannabidiol-Derived Neuroprotective Agent, with Improved Potency, Safety, and Permeability

  摘要：

  Cannabidiol is the nonpsychoactive natural component of C. sativa that has been shown to be neuroprotective in multiple animal models. Our interest is to advance a therapeutic candidate for the orphan indication hepatic encephalopathy (HE). HE is a serious neurological disorder that occurs in patients with cirrhosis or liver failure. Although cannabidiol is effective in models of HE, it has limitations in terms of safety and oral bioavailability. Herein, we describe a series of side chain modified resorcinols that were designed for greater hydrophilicity and "drug likeness", while varying hydrogen bond donors, acceptors, architecture, basicity, neutrality, acidity, and polar surface area within the pendent group. Our primary screen evaluated the ability of the test agents to prevent damage to hippocampal neurons induced by ammonium acetate and ethanol at clinically relevant concentrations. Notably, KLS-13019 was 50-fold more potent and >400-fold safer than cannabidiol and exhibited an in vitro profile consistent with improved oral bioavailability.

  DOI：

  10.1021/acsmedchemlett.6b00009
• 作为产物：
  描述：

  5-(3,5-二甲氧基苯基)戊酸乙酯 在 氢溴酸 、 溶剂黄146 作用下， 以2.5 g的产率得到5-(3,5-dihydroxyphenyl)pentanoic acid
  参考文献：
  名称：

  一种大麻二酚半抗原与完全抗原的制备方法及应用

  摘要：

  一种大麻二酚半抗原与完全抗原的制备方法及应用，大麻二酚半抗原是由3,5‑二甲氧基苯甲醛与三乙基‑4‑磷化物反应生成（2E，4E）‑5‑（3,5‑二甲氧基苯基）‑2,4‑戊二烯酸乙酯，随后经PdC/H2还原，HBr/HoAc脱甲基和皂化反应得到5‑（3,5‑二羟苯基）戊酸，最后再与(1S,4R)‑1‑甲基‑4‑(1‑甲基乙烯基)‑2‑环己烯‑1‑醇反应得到大麻二酚半抗原；大麻二酚完全抗原由大麻二酚半抗原与载体蛋白偶联得到。本发明制备的抗原呈现出特异性的大麻二酚抗原决定簇，使得筛选出高特异性的大麻二酚单克隆抗体成为可能。产生的抗体特异性高、灵敏度高，对大麻及其衍生物均无明显的交叉反应，可用于建立酶联免疫分析方法和胶体金、荧光快速检测试纸法，实现对样品中大麻二酚的快速检测。

  公开号：

  CN115160135B

文献信息

• Metabolism of (−)-Epigallocatechin Gallate by Rat Intestinal Flora
  作者：Akiko Takagaki、Fumio Nanjo

  DOI：10.1021/jf903375s

  日期：2010.1.27

  5′-trihydroxyphenyl)-3-(2′′,4′′,6′′-trihydroxyphenyl)propan-2-ol (3) by reductive cleavage between 1 and 2 positions of EGC, and subsequently metabolite 3 was converted to 1-(3′,5′-dihydroxyphenyl)-3-(2′′,4′′,6′′-trihydroxyphenyl)propan-2-ol (4) followed by the conversion to 5-(3,5-dihydroxyphenyl)-4-hydroxyvaleric acid (5) by decomposition of the phloroglucinol ring in metabolite 4. This degradation pathway

  体外研究了大鼠肠道细菌对（-）-表没食子儿茶素没食子酸酯（EGCg）的厌氧代谢。首先，用169株肠细菌筛选出能够将EGCg水解为（-）-表没食子儿茶素（EGC）和没食子酸（2）的肠细菌。结果，产生了产气肠杆菌，植物拉乌尔氏菌，肺炎克雷伯菌。肺炎和长双歧杆菌亚种。发现婴儿可以水解EGCg。EGCg代谢的后续步骤是EGC的降解（1）被肠道细菌感染。然后，将EGC与大鼠肠道细菌在0.1 M磷酸盐缓冲液（pH 7.1）中温育，并通过HPLC或LC-MS对降解产物进行时间分析。此外，由EGC形成的产物被分离并通过LC-MS和NMR分析鉴定。结果表明，EGC首先通过以下方法转化为1-（3'，4'，5'-三羟基苯基）-3-（2''，4''，6''-三羟基苯基）丙-2-醇（3）在EGC的1和2位之间进行还原性裂解，随后将代谢物3转化为1-（3'，5'-二羟基苯基）-3-（2''，4''，6''-三羟基苯基）丙烷-2-
• [EN] CANNABICHROMENIC ACID SYNTHASE FROM CANNABIS SATIVA<br/>[FR] ACIDE CANNABICHROMÉNIQUE SYNTHASE TIRÉE DE CANNABIS SATIVA
  申请人：NAT RES COUNCIL OF CANADA NRC

  公开号：WO2015196275A1

  公开（公告）日：2015-12-30

  Nucleic acid molecules from cannabis have been isolated and characterized and encode polypeptides having cannabichromenic acid synthase activity. Expression or over-expression of the nucleic acids alters levels of cannabinoid compounds. The polypeptides may be used in vivo or in vitro to produce cannabinoid compounds.

  大麻中的核酸分子已被分离和表征，并编码具有大麻二氢大麻酸合酶活性的多肽。核酸的表达或过表达改变了大麻素化合物的水平。这些多肽可以在体内或体外用于产生大麻素化合物。
• POLYFUNCTIONAL CANNABINOIDS
  申请人：Axim Biotechnologies, Inc.

  公开号：US20210332004A1

  公开（公告）日：2021-10-28

  This invention discloses cannabinoids linked with polyethylene glycol chains. The cannabinoid-polyethylene glycol chain molecules have one, two, or more cannabinoids linked with one, two, or more polyethylene glycol chains. Each cannabinoid-polyethylene glycol chain molecule may have one kind of cannabinoid or multiple kinds of cannabinoid. Methods to make these cannabinoid-polyethylene glycol linked chains are disclosed.

  这项发明揭示了与聚乙二醇链相连的大麻素。大麻素-聚乙二醇链分子具有一个、两个或更多个大麻素与一个、两个或更多个聚乙二醇链相连。每个大麻素-聚乙二醇链分子可能具有一种大麻素或多种大麻素。揭示了制造这些大麻素-聚乙二醇链的方法。
• [EN] SYNTHESIS AND PURIFICATION OF CANNABIGEROL AND ITS APPLICATION<br/>[FR] SYNTHÈSE ET PURIFICATION DE CANNABIGÉROL ET SON UTILISATION
  申请人：SYMRISE AG

  公开号：WO2020249184A1

  公开（公告）日：2020-12-17

  The present invention relates to a method for producing cannabigerol and purifying it from a reaction mixture. The present invention also relates to the cosmetic use of cannabigerol for the inhibition of tyrosinase activity and/or the reduction of melanin production in the skin, in particular for reducing pigmentation of the skin, preferably for the improvement of the appearance of the skin in case of hyperpigmentation, lentigo or vitiligo. Furthermore, the present invention relates to cannabigerol for use in a therapeutic method for the inhibition of tyrosinase activity and/or the reduction of melanin production in the skin, preferably for use in a therapeutic method for the treatment and/or prevention of malign skin disorders, in particular skin cancer.

  本发明涉及一种从反应混合物中生产大麻生酚并对其进行纯化的方法。本发明还涉及大麻生酚在化妆品中的应用，用于抑制酪氨酸酶活性和/或减少皮肤中黑色素的产生，特别是用于减少皮肤的色素沉着，优选用于改善皮肤在色素沉着过多、雀斑或白癜风等情况下的外观。此外，本发明涉及大麻生酚用于治疗方法，用于抑制皮肤中酪氨酸酶活性和/或减少黑色素的产生，特别是用于治疗和/或预防恶性皮肤疾病，特别是皮肤癌的治疗方法。
• Process for arylamine production
  申请人：Goodbrand Bruce H.

  公开号：US20060111582A1

  公开（公告）日：2006-05-25

  4-aminobiphenyl derivative arylamine compounds are formed by providing an iodinated organic compound; substituting the iodinated organic compound at carboxylic acid groups thereof to provide ester protecting groups; conducting an Ullman condensation reaction to convert the product of step (ii) into an arylamine compound; and conducting a Suzuki coupling reaction to add an additional phenyl group to the arylamine compound in the 4-position relative to the nitrogen.

  通过提供碘代有机化合物来形成4-氨基联苯衍生物芳胺化合物；用羧酸基取代碘代有机化合物以提供酯保护基；进行乌尔曼缩合反应将步骤（ii）的产物转化为芳胺化合物；并进行铃木偶联反应，在与氮相对的4位上向芳胺化合物中添加额外的苯基。