(8S,13S)-labda-15,19-dioic acid | 426813-32-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (8S,13S)-labda-15,19-dioic acid
• 英文别名: (1S,4aR,5S,6S,8aR)-5-[(3R)-4-carboxy-3-methylbutyl]-1,4a,6-trimethyl-2,3,4,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid
• CAS: 426813-32-3
• 化学式: C₂₀H₃₄O₄
• 分子量: 338.488
• InChiKey: VNMRKLQMHHSYDR-QORYDSDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (8S,13S)-labda-15,19-dioic acid 在 lithium aluminium tetrahydride 作用下， 生成 8αH-13Ξ-Labdan-15,19-diol
  参考文献：
  名称：

  Tabacik-Wlotzka,C. et al., Bulletin de la Societe Chimique de France, 1963, p. 2299 - 2306

  摘要：

  DOI：
• 作为产物：
  描述：

  异柏烯酸 在 Wilkinson's catalyst sodium chlorite 、 potassium dihydrogenphosphate 、 四丙基高钌酸铵 、 氢气 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 叔丁醇 、 苯 为溶剂， -5.0~55.0 ℃ 、413.68 kPa 条件下， 反应 30.5h， 生成 (8S,13S)-labda-15,19-dioic acid
  参考文献：
  名称：

  Preparation of Tetrahydroagathic Acid:  A Serum Metabolite of Isocupressic Acid, a Cattle Abortifacient in Ponderosa Pine

  摘要：

  Isocupressic acid (1) was used to synthetically prepare a mixture of (8S,13R,S)-labda-15,19-dioic acid (tetrahydroagathic acid) (5) via a two-step oxidation procedure followed by hydrogenation of the double bonds at C13 and C8. Reduction of the C8,17 double bond was stereospecific producing only the 8S isomer and confirmed by the nOe interaction between the resulting C17 and C20 methyl groups. The 13R and 13S isomers of 5 were separated and analyzed by HPLC/MS, and (13S)tetrahydroagathic acid was isolated and identified by comparison to a standard prepared by hydrogenation of naturally occurring (13S)-dihydroagathic acid (4). (13R,S)-dihydroagathic acid was prepared by selective sodium metal-catalyzed hydrogenation of the C13,14 allylic double bond of agathic acid (3). The prepared compounds were then used as standards to confirm the presence of 4 and 5 and their respective 13R and 13S isomers in bovine serum samples. Tetrahydroagathic acid was shown to be the only metabolite detected in serum samples taken from a suspected cattle abortion case submitted for diagnosis; and, thus, 5 could be a valuable diagnostic marker for pine needle-induced abortions.

  DOI：

  10.1021/jf011501m

文献信息

• Preparation of Tetrahydroagathic Acid:  A Serum Metabolite of Isocupressic Acid, a Cattle Abortifacient in Ponderosa Pine
  作者：Massoud Garrossian、Dale R. Gardner、Kip E. Panter、Lynn F. James

  DOI：10.1021/jf011501m

  日期：2002.4.1

  Isocupressic acid (1) was used to synthetically prepare a mixture of (8S,13R,S)-labda-15,19-dioic acid (tetrahydroagathic acid) (5) via a two-step oxidation procedure followed by hydrogenation of the double bonds at C13 and C8. Reduction of the C8,17 double bond was stereospecific producing only the 8S isomer and confirmed by the nOe interaction between the resulting C17 and C20 methyl groups. The 13R and 13S isomers of 5 were separated and analyzed by HPLC/MS, and (13S)tetrahydroagathic acid was isolated and identified by comparison to a standard prepared by hydrogenation of naturally occurring (13S)-dihydroagathic acid (4). (13R,S)-dihydroagathic acid was prepared by selective sodium metal-catalyzed hydrogenation of the C13,14 allylic double bond of agathic acid (3). The prepared compounds were then used as standards to confirm the presence of 4 and 5 and their respective 13R and 13S isomers in bovine serum samples. Tetrahydroagathic acid was shown to be the only metabolite detected in serum samples taken from a suspected cattle abortion case submitted for diagnosis; and, thus, 5 could be a valuable diagnostic marker for pine needle-induced abortions.
• Tabacik-Wlotzka,C. et al., Bulletin de la Societe Chimique de France, 1963, p. 2299 - 2306
  作者：Tabacik-Wlotzka,C. et al.

  DOI：——

  日期：——