12,13,17-trihydroxy-9(Z)-octadecenoic 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: 12,13,17-trihydroxy-9(Z)-octadecenoic acid
• 英文别名: (9z)-12,13,17-Trihydroxy-9-octadecenoic acid；(Z)-12,13,17-trihydroxyoctadec-9-enoic acid
• 化学式: C₁₈H₃₄O₅
• 分子量: 330.465
• InChiKey: IYIVYYHFHGVWRB-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 反应 72.0h， 以25%的产率得到12,13,17-trihydroxy-9(Z)-octadecenoic acid
  参考文献：
  名称：

  A novel compound, 12,13,17‐trihydroxy‐9(Z)‐Octadecenoic acid, from linoleic acid by a new microbial isolateClavibacter sp. ALA2

  摘要：

  摘要 利用微生物转化技术从亚油酸中生产出一种新型化合物--12,13,17-三羟基-9(Z)-十八碳烯酸（THOA），收率为 25%。新分离出的催化这一转化的微生物菌株被鉴定为克拉维氏菌 ALA2。产物经高压液相色谱法纯化，并通过 1H 和 13C 核磁共振、傅立叶变换红外光谱和质谱测定了其结构。反应 85 小时后，THOA 的产量达到最大。ALA2 菌株没有进一步代谢 THOA。这是首次报道 12、13、17-三羟基不饱和脂肪酸及其通过微生物转化产生的情况。

  DOI：

  10.1007/bf02523497

文献信息

• 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.
• 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.
• US5852196A
  申请人：——

  公开号：US5852196A

  公开（公告）日：1998-12-22
• US6310007B1
  申请人：——

  公开号：US6310007B1

  公开（公告）日：2001-10-30
• A novel compound, 12,13,17‐trihydroxy‐9(<i>Z</i>)‐Octadecenoic acid, from linoleic acid by a new microbial isolate<i>Clavibacter</i> sp. ALA2
  作者：Ching T. Hou

  DOI：10.1007/bf02523497

  日期：1996.11

  A novel compound, 12,13,17‐trihydroxy‐9(Z)‐octadecenoic acid (THOA), was produced from linoleic acid by microbial transformation at 25% yield. The newly isolated microbial strain that catalyzed this transformation was identified asClavibacter sp. ALA2. The product was purified by high‐pressure liquid chromatography, and its structure was determined by¹H and¹³C nuclear magnetic resonance, Fourier transform infrared, and mass spectroscopy. Maximum production of THOA was reached after 85 h of reaction. THOA was not further metabolized by strain ALA2. This is the first report on 12,13,17‐trihydroxy unsaturated fatty acid and its production by microbial transformation.

  摘要 利用微生物转化技术从亚油酸中生产出一种新型化合物--12,13,17-三羟基-9(Z)-十八碳烯酸（THOA），收率为 25%。新分离出的催化这一转化的微生物菌株被鉴定为克拉维氏菌 ALA2。产物经高压液相色谱法纯化，并通过 1H 和 13C 核磁共振、傅立叶变换红外光谱和质谱测定了其结构。反应 85 小时后，THOA 的产量达到最大。ALA2 菌株没有进一步代谢 THOA。这是首次报道 12、13、17-三羟基不饱和脂肪酸及其通过微生物转化产生的情况。