12-<5-ethyl-2-tetrahydrofuranyl>-12-hydroxy-9(Z)-dodecenoic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 12-<5-ethyl-2-tetrahydrofuranyl>-12-hydroxy-9(Z)-dodecenoic acid
• 英文别名: 12-hydroxy-13,16-epoxy-9(Z)-octadecenoic acid；(9Z)-12-Hydroxy-13,16-epoxy-9-octadecenoic acid；(Z)-12-(5-ethyloxolan-2-yl)-12-hydroxydodec-9-enoic acid
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: BLZRUYMMXDVEJR-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 Clavibacter sp. ALA₂ 作用下， 以 水 为溶剂， 反应 96.0h， 生成 12-<5-ethyl-2-tetrahydrofuranyl>-12-hydroxy-9(Z)-dodecenoic acid
  参考文献：
  名称：

  细杆菌属细菌从亚油酸生物合成四氢呋喃基脂肪酸。ALA2

  摘要：

  AbstractClavibacter sp. ALA2 converts linoleic acid into many novel oxygenated products including hydroxy FA and tetrahydrofuranyl unsaturated FA (THFA). One of them was tentatively identified by GC‐MS as 12,13,16‐trihydroxy‐9(Z)‐octadecenoic acid (12,13,16‐THOA) (Hou, C.T., H.W. Gardner, and W. Brown, J Am. Oil Chem. Soc. 78∶1167–1169, 2001). We have separated and purified 12,13,16‐THOA from its isomer, 12,13,17‐THOA, by silica gel column chromatography and by preparative TLC. Its structure was then confirmed by proton and 13C NMR analyses. Purified 12,13,16‐THOA was used as a substrate to study the biosynthesis of THFA. Within 24 h of incubation, cells of strain ALA2 converted 12,13,16‐THOA to both 12‐hydroxy‐13,16‐epoxy‐9(Z)‐octadecenoic acid (12‐hydroxy‐THFA) and 7,12‐dihydroxy‐13,16‐epoxy‐9(Z)‐octadecenoic acid (7,12‐dihydroxy‐THFA). The relative abundance of 7,12‐dihydroxy‐THFA increased with incubation time, whereas that of 12,13,16‐THOA and of 12‐hydroxy‐THFA decreased. Therefore, the biosynthetic pathway of THFA from linoleic acid by strain ALA2 is as follows: linoleic acid→12,13‐dihydroxy‐9(Z)‐octadecenoic acid→12,13,16‐THOA→12‐hydroxy‐THEA→7,12‐dihydroxy‐THFA.

  DOI：

  10.1007/s11746-003-0667-3

文献信息

• 12,13,16-trihydroxy-9(<i>Z</i> )-octadecenoic acid, a possible intermediate in the bioconversion of linoleic acid to tetrahydrofuranyl fatty acids by <i>Clavibacter</i> sp. ALA2
  作者：Ching T. Hou、Harold W. Gardner、Wanda Brown

  DOI：10.1007/s11746-001-0407-8

  日期：2001.11
• Production of polyhydroxy fatty acids from linoleic acid by<i>Clavibacter</i>sp. ALA2
  作者：Ching T. Hou、Harold Gardner、Wanda Brown

  DOI：10.1007/s11746-998-0082-z

  日期：1998.11

  AbstractHydroxy fatty acids are important industrial materials. We isolated a microbial culture, Clavibacter sp. ALA2, which converts linoleic acid to many polyhydroxy fatty acids. Structures of the products were determined as: 12,13,17‐trihydroxy‐9(Z)‐octadecenoic (THOA, main product), 12‐[5‐ethyl‐2‐tetrahydrofuranyl]‐7,12‐dihydroxy‐9(Z)‐dodecenoic (ETDDA), and 12‐[5‐ethyl‐2‐tetrahydrofuranyl]‐12‐hydroxy‐9(Z)‐dodecenoic (ETHDA) acid. The yield of THOA was 25% and the relative amount of the products were THOA/ETDDA/ETHDA =9:1.3:1. The structures of the hydroxy unsaturated fatty acids resemble those of plant self‐defense substances.
• Biosynthesis of tetrahydrofuranyl fatty acids from linoleic acid by <i>clavibacter</i> sp. ALA2
  作者：M. Hosokawa、C. T. Hou、D. Weisleder、W. Brown

  DOI：10.1007/s11746-003-0667-3

  日期：2003.2

  AbstractClavibacter sp. ALA2 converts linoleic acid into many novel oxygenated products including hydroxy FA and tetrahydrofuranyl unsaturated FA (THFA). One of them was tentatively identified by GC‐MS as 12,13,16‐trihydroxy‐9(Z)‐octadecenoic acid (12,13,16‐THOA) (Hou, C.T., H.W. Gardner, and W. Brown, J Am. Oil Chem. Soc. 78∶1167–1169, 2001). We have separated and purified 12,13,16‐THOA from its isomer, 12,13,17‐THOA, by silica gel column chromatography and by preparative TLC. Its structure was then confirmed by proton and 13C NMR analyses. Purified 12,13,16‐THOA was used as a substrate to study the biosynthesis of THFA. Within 24 h of incubation, cells of strain ALA2 converted 12,13,16‐THOA to both 12‐hydroxy‐13,16‐epoxy‐9(Z)‐octadecenoic acid (12‐hydroxy‐THFA) and 7,12‐dihydroxy‐13,16‐epoxy‐9(Z)‐octadecenoic acid (7,12‐dihydroxy‐THFA). The relative abundance of 7,12‐dihydroxy‐THFA increased with incubation time, whereas that of 12,13,16‐THOA and of 12‐hydroxy‐THFA decreased. Therefore, the biosynthetic pathway of THFA from linoleic acid by strain ALA2 is as follows: linoleic acid→12,13‐dihydroxy‐9(Z)‐octadecenoic acid→12,13,16‐THOA→12‐hydroxy‐THEA→7,12‐dihydroxy‐THFA.