5-(8Z-heptadecenyl) resorcinol | 184290-22-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-(8Z-heptadecenyl) resorcinol
• 英文别名: 5-(Heptadec-8-en-1-yl)benzene-1,3-diol；5-heptadec-8-enylbenzene-1,3-diol
• CAS: 184290-22-0
• 化学式: C₂₃H₃₈O₂
• 分子量: 346.554
• InChiKey: DQSWQRFGZIJUCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丙二酰辅酶A-钠盐 、 顺式-9-十八碳烯酰基辅酶 A 钾盐 在 alkylresorcylic acid synthase, ARAS₁ 作用下， 反应 0.33h， 生成 5-(8Z-heptadecenyl) resorcinol 、 、 1-(3,5-Dihydroxyphenyl)nonadec-10-en-2-one 、 、 2-(8-Heptadecenyl)-4,6-dihydroxybenzoic acid 、
  参考文献：
  名称：

  Alkylresorcylic acid synthesis by type III polyketide synthases from rice Oryza sativa

  摘要：

  Alkylresorcinols, produced by various plants, bacteria, and fungi, are bioactive compounds possessing beneficial activities for human health, such as anti-cancer activity. In rice, they accumulate in seedlings, contributing to protection against fungi. Alkylresorcylic acids, which are carboxylated forms of alkylresorcinols, are unstable compounds and decarboxylate readily to yield alkylresorcinols. Genome mining of the rice Oryza sativa identified two type III polyketide synthases, named ARAS1 (alkylresorcylic acid synthase) and ARAS2, that catalyze the formation of alkylresorcylic acids. Both enzymes condensed fatty acyl-CoAs with three C-2 units from malonyl-CoA and cyclized the resulting tetraketide intermediates via intramolecular C-2 to C-7 aldol condensation. The alkylresorcylic acids thus produced were released from the enzyme and decarboxylated non-enzymatically to yield alkylresorcinols. This is the first report on a plant type III polyketide synthase that produces tetraketide alkylresorcylic acids as major products. (C)2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.phytochem.2010.02.012

文献信息

• Alkylresorcylic acid synthesis by type III polyketide synthases from rice Oryza sativa
  作者：Miku Matsuzawa、Yohei Katsuyama、Nobutaka Funa、Sueharu Horinouchi

  DOI：10.1016/j.phytochem.2010.02.012

  日期：2010.7

  Alkylresorcinols, produced by various plants, bacteria, and fungi, are bioactive compounds possessing beneficial activities for human health, such as anti-cancer activity. In rice, they accumulate in seedlings, contributing to protection against fungi. Alkylresorcylic acids, which are carboxylated forms of alkylresorcinols, are unstable compounds and decarboxylate readily to yield alkylresorcinols. Genome mining of the rice Oryza sativa identified two type III polyketide synthases, named ARAS1 (alkylresorcylic acid synthase) and ARAS2, that catalyze the formation of alkylresorcylic acids. Both enzymes condensed fatty acyl-CoAs with three C-2 units from malonyl-CoA and cyclized the resulting tetraketide intermediates via intramolecular C-2 to C-7 aldol condensation. The alkylresorcylic acids thus produced were released from the enzyme and decarboxylated non-enzymatically to yield alkylresorcinols. This is the first report on a plant type III polyketide synthase that produces tetraketide alkylresorcylic acids as major products. (C)2010 Published by Elsevier Ltd.