12-hydroxytremetone | 35844-67-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 12-hydroxytremetone
• 英文别名: bitalin A；[2,3-dihydro-2-[1-(hydroxymethyl)ethenyl]-5-benzofuranyl]ethanone；1-[(2R)-2-(3-hydroxyprop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethanone
• CAS: 35844-67-8
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: JRWKMIYLVXKKAN-CYBMUJFWSA-N

物化性质

• 沸点：
  404.1±45.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  壬酸 、 12-hydroxytremetone 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以60%的产率得到nonanoylbitalin A
  参考文献：
  名称：

  Antimicrobial Phenolics and Unusual Glycerides from Helichrysum italicum subsp. microphyllum

  摘要：

  During a large-scale isolation campaign for the heterodimeric phloroglucinyl pyrone arzanol (1a) from Helichrysum italicum subsp. microphyllum, several new phenolics as well as an unusual class of lipids named santinols (5a-c, 6-8) have been characterized. Santinols are angeloylated glycerides characterized by the presence of branched acyl- or keto-acyl chains and represent a hitherto unreported class of plant lipids. The antibacterial activity of arzanol and of a selection of Helichrysum phenolics that includes coumarates, benzofurans, pyrones, and heterodimeric phloroglucinols was evaluated, showing that only the heterodimers showed potent antibacterial action against multidrug-resistant Staphylococcus aureus isolates. These observations validate the topical use of Helichrysum extracts to prevent wound infections, a practice firmly established in the traditional medicine of the Mediterranean area.

  DOI：

  10.1021/np3007149
• 作为产物：
  描述：

  2,3-dihydrobenzofuran-2(R)-carboxylic acid 在 selenium(IV) oxide 、 三氟乙酸酐 作用下， 生成 12-hydroxytremetone
  参考文献：
  名称：

  福曼诺辛、(-)-5-乙酰-2-(1-羟基甲基乙烯基)-2,3-二氢苯并呋喃和阳极树酸的合成和绝对构型

  摘要：

  标题化合物由(-)-(S)-或(+)-(R)-2,3-二氢苯并呋喃-2-羧酸合成。并且确定了它们的绝对构型。

  DOI：

  10.1246/cl.1980.1581

文献信息

• Omar, Abdallah A.; El-Ghazouly, Maged G.; Bohlmann, Ferdinand, Liebigs Annalen der Chemie, 1983, # 8, p. 1451 - 1454
  作者：Omar, Abdallah A.、El-Ghazouly, Maged G.、Bohlmann, Ferdinand、Zdero, Christa

  DOI：——

  日期：——
• Antimicrobial Phenolics and Unusual Glycerides from <i>Helichrysum italicum</i> subsp. <i>microphyllum</i>
  作者：Orazio Taglialatela-Scafati、Federica Pollastro、Giuseppina Chianese、Alberto Minassi、Simon Gibbons、Warunya Arunotayanun、Blessing Mabebie、Mauro Ballero、Giovanni Appendino

  DOI：10.1021/np3007149

  日期：2013.3.22

  During a large-scale isolation campaign for the heterodimeric phloroglucinyl pyrone arzanol (1a) from Helichrysum italicum subsp. microphyllum, several new phenolics as well as an unusual class of lipids named santinols (5a-c, 6-8) have been characterized. Santinols are angeloylated glycerides characterized by the presence of branched acyl- or keto-acyl chains and represent a hitherto unreported class of plant lipids. The antibacterial activity of arzanol and of a selection of Helichrysum phenolics that includes coumarates, benzofurans, pyrones, and heterodimeric phloroglucinols was evaluated, showing that only the heterodimers showed potent antibacterial action against multidrug-resistant Staphylococcus aureus isolates. These observations validate the topical use of Helichrysum extracts to prevent wound infections, a practice firmly established in the traditional medicine of the Mediterranean area.
• THE SYNTHESES AND ABSOLUTE CONFIGURATIONS OF FOMANNOXIN, (−)-5-ACETYL-2-(1-HYDROXYMETHYLVINYL)-2,3-DIHYDROBENZOFURAN, AND ANODENDROIC ACID
  作者：Yoshiyuki Kawase、Seiji Yamaguchi、Osamu Inoue、Michiko Sannomiya、Kazuko Kawabe

  DOI：10.1246/cl.1980.1581

  日期：1980.12.5

  The title compounds were synthesized from (−)-(S)- or (+)-(R)-2,3-dihydrobenzofuran-2-carboxylic acid. And their absolute configurations were determined.

  标题化合物由(-)-(S)-或(+)-(R)-2,3-二氢苯并呋喃-2-羧酸合成。并且确定了它们的绝对构型。