灰叶酸 | 80557-12-6

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 灰叶酸
• 英文名称: Grifolic acid
• 英文别名: 2,4-dihydroxy-6-methyl-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)benzoic acid；ilicicolinic acid B；Grifolsaeure；2,4-dihydroxy-6-methyl-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzoic acid
• CAS: 80557-12-6
• 化学式: C₂₃H₃₂O₄
• 分子量: 372.505
• InChiKey: QPIZDZGIXDKCRC-JTCWOHKRSA-N

物化性质

• 熔点：
  93-94 °C(Solv: hexane (110-54-3))
• 沸点：
  557.1±50.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 储存条件：
  存放在2-8℃的环境中，应保持干燥并密封。

制备方法与用途

生物活性

Grifolic酸是一种从Albatrellus confluens蘑菇中提取的酚类化合物，作为游离脂肪酸受体（FFAR4/GPR120）的激动剂。

体外研究

Grifolic酸在浓度为2.5-20 µM时，以剂量和时间依赖性的方式减少RAW264.7细胞的存活率。

反应信息

• 作为反应物：
  描述：

  灰叶酸 在 甲醇 、 sodium hydroxide 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 9.0h， 生成 (2R,3S)-2-[(3E)-4,8-dimethylnona-3,7-dienyl]-2,7-dimethyl-3,4-dihydrochromene-3,5-diol
  参考文献：
  名称：

  Ishii, Naoyuki; Takahashi, Akira; Kusano, Genjiro, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 8, p. 2918 - 2924

  摘要：

  DOI：
• 作为产物：
  描述：

  7-hydroxy-2,2,5-trimethyl-8-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl)-4H-benzo[d][1,3]dioxin-4-one 在 potassium tert-butylate 、 水 作用下， 以 乙醚 为溶剂， 反应 72.0h， 以89%的产率得到灰叶酸
  参考文献：
  名称：

  萜类化合物的全合成：二恶英酮-β-酮酰化，钯催化的脱羧烯丙基重排和芳构化，将香叶醇和法尼醇转化为非晶形固醇，草甘膦和草酸

  摘要：

  间苯二酚amorphastilbol，grifolin和grifolic acid的仿生总合成已从香叶醇和法尼醇开始的四个步骤中完成，无需使用酚类保护剂。关键步骤包括二恶英酮-β-酮酯的C-酰化，然后钯催化的脱羧烯丙基重排和仿生芳构化。

  DOI：

  10.1016/j.tetlet.2017.05.096

文献信息

• Isolation, Synthesis and Biological Activity of Grifolic Acid Derivatives from the Inedible Mushroom Albatrellus dispansus
  作者：Yoshinori Asakawa、Toshihiro Hashimoto、Dang Ngoc Quang、Makiko Nukada

  DOI：10.3987/com-05-10501

  日期：——
• GLUCAGON SUPERFAMILY PEPTIDES EXHBITING G PROTEIN COUPLED RECEPTOR ACTIVITY
  申请人：Dimarchi Richard D.

  公开号：US20130116172A1

  公开（公告）日：2013-05-09

  Provided herein are glucagon superfamily peptides conjugated with GPCR ligands that are capable of acting at a G protein-coupled receptor. Also provided herein are pharmaceutical compositions and kits of the conjugates of the invention. Further provided herein are methods of treating a disease, e.g., a metabolic disorder, such as diabetes and obesity, comprising administering the conjugates of the invention.
• GLUCAGON SUPERFAMILY PEPTIDES EXHIBITING G PROTEIN-COUPLED RECEPTOR ACTIVITY
  申请人：Indiana University Research and Technology Corporation

  公开号：US20160051688A1

  公开（公告）日：2016-02-25

  Provided herein are glucagon superfamily peptides conjugated with GPCR ligands that are capable of acting at a G protein-coupled receptor. Also provided herein are pharmaceutical compositions and kits of the conjugates of the invention. Further provided herein are methods of treating a disease, e.g., a metabolic disorder, such as diabetes and obesity, comprising administering the conjugates of the invention.
• INHIBITORS OF FAPP2 AND USES THEREOF
  申请人：FONDAZIONE TELETHON

  公开号：US20160250221A1

  公开（公告）日：2016-09-01

  The present invention provides methods and compositions for reducing globotriaosylceramide (Gb3) accumulation and treating diseases, disorders or conditions associated with Gb3 accumulation based on inhibitors of phosphatidylinositol-4-phosphate adaptor-2 (FAPP2), including interfering oligonucleotides, for example, siRNAs, and small molecule compounds based inhibitors. The present invention is particularly useful in treating Fabry disease and other sphingolipidoses relating to sphingolipid metabolism, such as Gaucher's disease.
• METHOD OF PRODUCING ISOPRENOIDS AND PROTEINS, GENES, AND TRANSFORMANTS FOR THE SAME
  申请人：KIKKOMAN CORPORATION

  公开号：US20200063143A1

  公开（公告）日：2020-02-27

  The problem to be solved by the present invention is to provide a method of producing isoprenoids including ascofuranone, ilicicolin A, and ascochlorin and derivatives thereof in a high yield as compared to the conventional art, which method enables industrial-scale production of isoprenoids. The problem can be solved by a method of producing isoprenoids such as ascofuranone, ilicicolin A, and ascochlorin, including using a transformant obtained by transformation with biosynthetic genes for ascofuranone, ilicicolin A, or ascochlorin or a knockout organism for these genes to obtain isoprenoids such as ascofuranone, ilicicolin A, and ascochlorin.