内黄素 | 481-70-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 内黄素
• 中文别名: 2,3-噁丙环二羧酸,2-(1-甲基乙基)-,顺-(9CI)
• 英文名称: endocrocin
• 英文别名: 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone-2-carboxylic acid；1,6,8-trihydroxy-3-methyl-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid；1,6,8-Trihydroxy-3-methyl-9,10-dioxo-9,10-dihydro-anthracen-2-carbonsaeure；1,6,8-trihydroxy-3-methyl-9,10-dioxoanthracene-2-carboxylic acid
• CAS: 481-70-9
• 化学式: C₁₆H₁₀O₇
• 分子量: 314.251
• InChiKey: UZOHDKGTYVTYDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  318 °C (decomp)(Solv: acetic acid (64-19-7))
• 沸点：
  679.7±55.0 °C(Predicted)
• 密度：
  1.715±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  内黄素 生成 大黄素
  参考文献：
  名称：

  Asahina; Fuzikawa, Chemische Berichte, 1935, vol. 68, p. 1558,1563

  摘要：

  DOI：
• 作为产物：
  描述：

  tri-O-methyl endocrocin 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以78%的产率得到内黄素
  参考文献：
  名称：

  An efficient regioselective synthesis of endocrocin and structural related natural anthraquinones starting from emodin

  摘要：

  Endocrocin and related naturally occurring anthraquinone pigments like cinnalutein could be synthesized regioselectively via a Marschalk type reaction, starting from the natural hydroxy anthraquinone emodin. Furthermore, the new tri-O-methyl protected emodin-2-carbaldehyde may serve as a promising synthon for new bathochromically shifted, higher generation photodynamically active hypericin derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.061

文献信息

• Studies on Nepalese Crude Drugs. XXV. Phenolic Constituents of the Leaves of Didymocarpus leucocalyx C.B. CLARKE (Gesneriaceae).
  作者：Akiko SEGAWA、Yukinori MIYAICHI、Tsuyoshi TOMIMORI、Fumiyuki KIUCHI、Tomihisa OHTA

  DOI：10.1248/cpb.47.1404

  日期：——

  Seven new phenolic compounds (8-14) including three ones having unique structure named didymocalyxins A (12), B (13) and C (14) have been isolated from the leaves of Didymocarpus leucocalyx, along with five known flavonoids (5-hydroxy-6, 7-dimethoxyflavanone, 5, 8-dihydroxy-6, 7-dimethoxyflavanone, 2', 6'-dihydroxy-3', 4'-dimethoxychalcone, 3'-hydroxy-2', 4', 5', 6'-tetramethoxychalcone and 2', 5'-dihydroxy-4'-methoxy-3', 6'-dioxochalcone) and two known anthraquinoids (physcion and catenarin). The structures of 8-14 were determined to be 3', 4-dihydroxy-2', 4', 5', 6'-tetramethoxychalcone (8), 5, 8-dihydroxy-6, 7-dimethoxyisoflavone (9), 1, 6, 8-trihydroxy-4-benzoyloxy-3-methylanthraquinone (10), (2S)-2, 3-dihydroxypropyl 1, 6, 8-trihydroxy-3-methyl-9, 10-dioxoanthracene-2-carboxylate (11), (±)-1, 4-dihydroxy-2, 3, 6, 7-tetramethoxy-10-phenyl-9, 10-dihydrocyclohepta[2, 1-b]4H-chromene-8, 11-dione (12), 3-((1E, 2E)-1-hydroxy-3-phenylprop-2-enylidene)-7-((2E)-3-phenylprop-2-enoyl)-6-hydroxy-4, 5-dimethoxybenzo[b]furan-2-one (13) and 2((1E)-2-phenylvinyl)-5, 6-dihydroxy-7, 8-dimethoxy-4H-pyrano[3, 2-d]benzo[b]furan-4-one (14) on the basis of chemical and spectroscopic evidence and X-ray analysis.

  从白花蛇舌草（Didymocarpus leucocalyx）叶片中分离出七种新的酚类化合物（8-14），其中包括三种具有独特结构的化合物，分别命名为白花蛇舌草素 A（12）、白花蛇舌草素 B（13）和白花蛇舌草素 C（14）、5，8-二羟基-6，7-二甲氧基黄烷酮、2'，6'-二羟基-3'，4'-二甲氧基查尔酮、3'-羟基-2'，4'，5'，6'-四甲氧基查尔酮和 2'，5'-二羟基-4'-甲氧基-3'，6'-二氧查尔酮）以及两种已知的蒽醌类化合物（physcion 和 catenarin）。8-14 的结构被确定为 3'，4-二羟基-2'，4'，5'，6'-四甲氧基查尔酮（8），5，8-二羟基-6，7-二甲氧基异黄酮（9），1，6、1，6，8-三羟基-4-苯甲酰氧基-3-甲基蒽醌 (10)、(2S)-2，3-二羟基丙基 1，6，8-三羟基-3-甲基-9，10-二氧代蒽-2-羧酸酯 (11)、(±)-1，4-二羟基-2，3，6，7-四甲氧基-10-苯基-9、10-二氢环庚二烯并[2，1-b]4H-苯并吡喃-8，11-二酮 (12)、3-((1E，2E)-1-羟基-3-苯基丙-2-亚烯基)-7-((2E)-3-苯基丙-2-烯酰)-6-羟基-4、根据化学和光谱证据以及 X 射线分析，我们还发现了 2((1E)-2-苯基乙烯基)-5，6-二羟基-7，8-二甲氧基-4H-吡喃并[3，2-d]苯并[b]呋喃-4-酮 (13) 和 2((1E)-2-苯基乙烯基)-5，6-二羟基-7，8-二甲氧基-4H-吡喃并[3，2-d]苯并[b]呋喃-4-酮 (14)。
• Physically Discrete β-Lactamase-Type Thioesterase Catalyzes Product Release in Atrochrysone Synthesis by Iterative Type I Polyketide Synthase
  作者：Takayoshi Awakawa、Kosuke Yokota、Nobutaka Funa、Fuminao Doi、Naoki Mori、Hidenori Watanabe、Sueharu Horinouchi

  DOI：10.1016/j.chembiol.2009.04.004

  日期：2009.6

  ATEG_08451 in Aspergillus terreus, here named atrochrysone carboxylic acid synthase (ACAS), is a nonreducing, iterative type I polyketide synthase that contains no thioesterase domain. In vitro, reactions of ACAS with malonyl-CoA yielded a polyketide intermediate, probably attached to its acyl carrier protein (ACP). The addition of ATEG_08450, here named atrochrysone carboxyl ACP thioesterase (ACTE), to the reaction resulted in the release of products derived from atrochrysone carboxylic acid, such as atrochrysone and endocrocin. ACTE, belonging to the beta-lactamase superfamily, thus appears to be a novel type of thioesterase responsible for product release in polyketide biosynthesis. These findings show that ACAS synthesizes the scaffold of atrochrysone carboxylic acid from malonyl-CoA, and that ACTE hydrolyzes the thioester bond between the ACP of ACAS and the intermediate to release atrochrysone carboxylic acid as the reaction product.
• TOMM6-INTERACTING EXTRACTS AND COMPOUNDS FOR USE IN THE TREATMENT AND PROPHYLAXIS OF NERVOUS SYSTEM DISEASES, ATHEROSCLEROSIS, HEPATITIS B INFECTION AND HUMAN PAPILLOMA VIRUS (HPV) INFECTION
  申请人：ETH Zurich

  公开号：EP3801507A2

  公开（公告）日：2021-04-14
• An efficient regioselective synthesis of endocrocin and structural related natural anthraquinones starting from emodin
  作者：Mario Waser、Bernd Lackner、Joachim Zuschrader、Norbert Müller、Heinz Falk

  DOI：10.1016/j.tetlet.2005.02.061

  日期：2005.4

  Endocrocin and related naturally occurring anthraquinone pigments like cinnalutein could be synthesized regioselectively via a Marschalk type reaction, starting from the natural hydroxy anthraquinone emodin. Furthermore, the new tri-O-methyl protected emodin-2-carbaldehyde may serve as a promising synthon for new bathochromically shifted, higher generation photodynamically active hypericin derivatives. (c) 2005 Elsevier Ltd. All rights reserved.
• Asahina; Fuzikawa, Chemische Berichte, 1935, vol. 68, p. 1558,1563
  作者：Asahina、Fuzikawa

  DOI：——

  日期：——