15-carboxymethyloxyisocupressic acid | 540777-56-8

• 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: 15-carboxymethyloxyisocupressic acid
• CAS: 540777-56-8
• 化学式: C₂₂H₃₄O₅
• 分子量: 378.509
• InChiKey: NSIWJEZPGOOJDQ-PPOPNMGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 15-carboxymethyloxyisocupressic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 16.0h， 生成 (1S,4aR,5S,8aR)-5-[(E)-5-(2,5-Dioxo-pyrrolidin-1-yloxycarbonylmethoxy)-3-methyl-pent-3-enyl]-1,4a-dimethyl-6-methylene-decahydro-naphthalene-1-carboxylic acid
  参考文献：
  名称：

  Development of Enzyme-Linked Immunosorbent Assays for Isocupressic Acid and Serum Metabolites of Isocupressic Acid

  摘要：

  The consumption of ponderosa pine (Pinus ponderosa), lodgepole pine (Pinus contorta), common juniper (Juniperus communis), and Monterey cypress (Cupressus macrocarpa) causes abortions in pregnant cattle. Recent studies have identified isocupressic acid (1) as the primary abortificient compound in these plants. In vitro and in vivo studies using rumen and blood have shown isocupressic acid (1) is rapidly metabolized to agathic acid (3), dihydroagathic acid (4), and tetrahydroagathic acid (5). Rapid and sensitive diagnostic techniques are needed to identify poisoned animals, to study toxicokinetics, and to elucidate the mechanism of isocupressic acid-induced abortion in cattle. In this study, four competitive inhibition enzyme-linked immunosorbent assays for isocupressic acid and its sera metabolites were developed using polyclonal antibodies. One assay is specific to 1, whereas the other three assays show cross-reactivity to 3-5 in addition to 1. The assay specific to 1 had a limit of detection of 44.1 pg. The other assays which demonstrated cross-reactivity to the isocupressic acid blood metabolites also had comparably low limits of detection. One assay was used to follow the absorption and elimination profile of isocupressic acid metabolites in both cow serum and urine after oral dosage of a cow with common juniper.

  DOI：

  10.1021/jf021095m
• 作为产物：
  描述：

  15-methoxycarbonylmethyloxyisocupressic acid 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以39%的产率得到15-carboxymethyloxyisocupressic acid
  参考文献：
  名称：

  Development of Enzyme-Linked Immunosorbent Assays for Isocupressic Acid and Serum Metabolites of Isocupressic Acid

  摘要：

  The consumption of ponderosa pine (Pinus ponderosa), lodgepole pine (Pinus contorta), common juniper (Juniperus communis), and Monterey cypress (Cupressus macrocarpa) causes abortions in pregnant cattle. Recent studies have identified isocupressic acid (1) as the primary abortificient compound in these plants. In vitro and in vivo studies using rumen and blood have shown isocupressic acid (1) is rapidly metabolized to agathic acid (3), dihydroagathic acid (4), and tetrahydroagathic acid (5). Rapid and sensitive diagnostic techniques are needed to identify poisoned animals, to study toxicokinetics, and to elucidate the mechanism of isocupressic acid-induced abortion in cattle. In this study, four competitive inhibition enzyme-linked immunosorbent assays for isocupressic acid and its sera metabolites were developed using polyclonal antibodies. One assay is specific to 1, whereas the other three assays show cross-reactivity to 3-5 in addition to 1. The assay specific to 1 had a limit of detection of 44.1 pg. The other assays which demonstrated cross-reactivity to the isocupressic acid blood metabolites also had comparably low limits of detection. One assay was used to follow the absorption and elimination profile of isocupressic acid metabolites in both cow serum and urine after oral dosage of a cow with common juniper.

  DOI：

  10.1021/jf021095m