长叶松酸 | 1945-53-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 环羧酸
• 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
• 中文名称: 长叶松酸
• 中文别名: 沼泽酸
• 英文名称: palustric acid
• 英文别名: Palustrinsaeure；(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,5,6,9,10,10a-octahydrophenanthrene-1-carboxylic acid
• CAS: 1945-53-5
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: MLBYBBUZURKHAW-MISYRCLQSA-N

物化性质

• 熔点：
  162-167°
• 比旋光度：
  D +71.6°
• 沸点：
  383.47°C (rough estimate)
• 密度：
  1.0434 (rough estimate)
• 溶解度：
  可溶于氯仿（轻微）、DMSO（轻微、超声处理）、乙醇（轻微、超声处理）
• LogP：
  6.620 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

制备方法与用途

概述

沼泽酸（Palustric acid）是一种二萜酸类化合物，熔点为162-167℃。药理研究表明，它具有拒食作用，并对锯角叶锋等植物有强烈的拒食效果。

用途

沼泽酸广泛存在于柏科植物刺桧（Juniperus axycedrus L.）、松科植物马尾松（Pinus massoniana Lamb.）和长叶松（Pinus palustris Mill.）中。该化合物具有抗血小板聚集的作用，能够抑制兔血小板由PAF、ADP和钙离子甾体诱导的聚集。

生物活性

沼泽酸是一种在黑松中发现的二萜树脂酸。

反应信息

• 作为反应物：
  描述：

  长叶松酸 在 air 、 乙醇 、 Eosin Y 作用下， 生成 abieta-8(14)-en-18-oic acid 9α,13α-endoperoxide
  参考文献：
  名称：

  Agrobacterium tumefaciens — mediated Transformation of Rice Using Coleoptile and Mature Seed-derived Callus

  摘要：

  Morphologically normal, fertile transgenic rice plants (Oryza sativa L cv Taipei 309) were obtained using Agrobacterium tumefaciens strain LBA4404 harbouring the plasmid pTOK233. Two transgenic systems were developed. The first involved callus derived from mature seeds (scutellum) and, the second, used callus derived from 4-d-old coleoptiles. This is the first time that a coleoptile-based system has been used for producing transgenic rice plants. In the development of coleoptile based system, we have evaluated the effect of the length of callus induction period of the coleoptiles on transformation efficiency. The proportion of GUS positive plants was 23% in coleoptile experiment while in mature seed experiments it was 21%. Southern analyses were done to confirm the presence of the transgene. It was found that one to three copies of the transgene integrated in the transgenic plants.

  DOI：

  10.1007/bf03263120
• 作为产物：
  描述：

  p-nitrophenyl palustrate 在 氢氧化钾 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 长叶松酸
  参考文献：
  名称：

  Cheung; Fu; Smal, Arzneimittel-Forschung/Drug Research, 1994, vol. 44, # 1, p. 17 - 25

  摘要：

  DOI：

文献信息

• HEAT-RESISTANT ALIPHATIC-CHAIN SATURATED HYDROCARBON HAVING ION PAIRS AT BOTH ENDS, AND COMPOSITION USING SAME
  申请人：Kaneka Corporation

  公开号：US20180029992A1

  公开（公告）日：2018-02-01

  An aliphatic-chain saturated hydrocarbon including an aliphatic hydrocarbon chain which is saturated and has an ion pair at each end of the aliphatic hydrocarbon chain.

  一种包括饱和脂肪烃链的脂肪链饱和烃，该脂肪烃链是饱和的，并且在脂肪烃链的每一端具有一个离子对。
• Synthesis and characterization of abietadiene, levopimaradiene, palustradiene, and neoabietadiene: hydrocarbon precursors of the abietane diterpene resin acids
  作者：Hyung-Jae Lee、Matthew M. Ravn、Robert M. Coates

  DOI：10.1016/s0040-4020(01)00605-6

  日期：2001.7

  The abietane diterpenes—abietadiene, levopimaradiene, palustradiene, and neoabietadiene (1b–4b)—were prepared from the corresponding resin acids by diazomethane esterifications, LiAlH4 reductions, tosylations, and Zn/NaI reductions. Abietadiene was also obtained less efficiently by catechol borane reduction of abietadienal tosylhydrazone and Li/NH3 reduction of its 18-phenylthio derivative. These conjugated

  通过重氮甲烷酯化，LiAlH 4还原，甲苯磺酰化和Zn / NaI还原，由相应的树脂酸制备了Abettane二萜-abietadiene，levopimaradiene，palustradiene和neoabietadiene（1b - 4b）。还可以通过邻苯二酚对甲苯磺酰hydr的邻苯二酚硼烷还原和其18-苯硫基衍生物的Li / NH 3还原而不太有效地获得己二烯。这些共轭二烯的特征在于色谱特性（HPLC，TLC，GC），MS碎裂模式，旋光度以及UV，IR，1 H NMR和13 C NMR数据。1 H和13的分配C NMR光谱由COSY，DEPT，HMQC，HMBC，NOE数据，H–H耦合分析以及与文献数据的比较得出。四个二萜被鉴定为重组松果油二烯合酶的环化产物，支持了它们在针叶树油树脂中松果油树脂酸的生物合成中的可能作用。
• Rosin-Derived Cationic Compounds and Polymers Along with Their Methods of Preparation
  申请人：Tang Chuanbing

  公开号：US20120214950A1

  公开（公告）日：2012-08-23

  Methods for forming rosin-derived cationic compounds are provided. The method can include attaching a cationic group to a conjugated diene on a hydrophenathrene-based ring of a resin acid (e.g., levopimaric acid, abietic acid, dehydroabietic acid, or a mixture thereof) to form a rosin-derived cationic compound. Attaching the cationic group to the conjugated diene on the hydrophenathrene-based ring of the resin acid can be achieved via a Diels-Alder reaction of a dienophile with the hydrophenathrene-based ring of the resin acid. Rosin-derived cationic compounds are also provided. The rosin-derived cationic compound can include a cationic group attached to a conjugated diene on a hydrophenathrene-based ring of a resin acid, wherein the rosin-derived cationic compound further comprises a carboxylic acid group.

  提供了制备松香衍生阳离子化合物的方法。该方法可以包括将阳离子基团连接到树脂酸（例如左旋松香酸、松香酸、脱氢松香酸或其混合物）的一个基于羟基苯并环的环上的共轭二烯上，以形成松香衍生阳离子化合物。通过将阳离子基团连接到树脂酸基于羟基苯并环的环上的共轭二烯，可以通过二烯丙烯与树脂酸基于羟基苯并环的环的Diels-Alder反应来实现。还提供了松香衍生阳离子化合物。该松香衍生阳离子化合物可以包括连接到树脂酸基于羟基苯并环的环上的共轭二烯上的阳离子基团，其中该松香衍生阳离子化合物还包括一个羧酸基团。
• ANTIMICROBIAL COMPOSITION
  申请人：De Leij Franciscus Antonius Anna Maria

  公开号：US20130045954A1

  公开（公告）日：2013-02-21

  Antimicrobial compositions comprising a terpenoid in combination with an antimicrobial agent are provided. In addition, uses of such compositions in various applications involving preventing, combating or treating microbial infections, or preventing microbial growth or establishment are provided.

  提供了含有萜类化合物和抗微生物剂的抗微生物组合物。此外，还提供了在各种应用中使用这种组合物的方法，包括预防、对抗或治疗微生物感染，或预防微生物生长或建立。
• Rosin-Derived Cationic Compounds and Polymers
  申请人：Tang Chuanbing

  公开号：US20140163174A1

  公开（公告）日：2014-06-12

  Methods for forming rosin-derived cationic compounds are provided. The method can include attaching a cationic group to a conjugated diene on a hydrophenathrene-based ring of a resin acid (e.g., levopimaric acid, abietic acid, dehydroabietic acid, or a mixture thereof) to form a rosin-derived cationic compound. Attaching the cationic group to the conjugated diene on the hydrophenathrene-based ring of the resin acid can be achieved via a Diels-Alder reaction of a dienophile with the hydrophenathrene-based ring of the resin acid. Rosin-derived cationic compounds are also provided. The rosin-derived cationic compound can include a cationic group attached to a conjugated diene on a hydrophenathrene-based ring of a resin acid, wherein the rosin-derived cationic compound further comprises a carboxylic acid group.

  提供了制备松香衍生阳离子化合物的方法。该方法可以包括将阳离子基团连接到树脂酸（例如左旋松香酸、松香酸、脱氢松香酸或其混合物）的羟基苯并[3.3.1]环上的共轭二烯上，形成松香衍生阳离子化合物。通过二烯丙烯与树脂酸的羟基苯并[3.3.1]环进行Diels-Alder反应，可以将阳离子基团连接到树脂酸的羟基苯并[3.3.1]环上。还提供了松香衍生阳离子化合物。该松香衍生阳离子化合物可以包括连接到树脂酸的羟基苯并[3.3.1]环上的共轭二烯上的阳离子基团，其中该松香衍生阳离子化合物进一步包括一个羧酸基团。

表征谱图