labdanolic acid | 469-11-4

• 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: labdanolic acid
• 英文别名: (3S)-5-[(1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpentanoic acid
• CAS: 469-11-4
• 化学式: C₂₀H₃₆O₃
• 分子量: 324.504
• InChiKey: KHCCSRVJJDOANA-RQOBALISSA-N

物化性质

• 沸点：
  439.3±18.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  labdanolic acid 在 吡啶 、 lithium aluminium tetrahydride 、 碘苯二乙酸 、 potassium tert-butylate 、 碘 、 对甲苯磺酸 、 臭氧 、 N,N-二甲基苯胺 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 硝基甲烷 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 降龙涎香醚
  参考文献：
  名称：

  The synthesis of (−)-Ambrox® starting from labdanolic acid

  摘要：

  Iododecarboxylation of labdanolic acid (1), followed by dehydrohalogenation led to alkenes 4 and 12. Both compounds were converted into (1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyldecahydro-2-naphthalenol (8), which was transformed via cyclization into (-)-Ambrox((R)) (9). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00493-8
• 作为产物：
  描述：

  13(S)-labdan-8α,15-diol 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以60.3%的产率得到labdanolic acid
  参考文献：
  名称：

  Evaluation of labdane derivatives as potential anti-inflammatory agents

  摘要：

  In the present study, a series of labdane derivatives (2-9) were prepared from labdanediol (1) and their potential as anti-inflammatory agents were evaluated on lipopolysaccharide (LPS)-treated RAW 264.7 macrophages. All compounds were able to inhibit LPS-induced nitric oxide (NO), although compounds 1, 2, 5, 8 and 9 exhibited the most potent effects with a range of IC50 values of 5-15 mu M. Similarly to the inhibitory effects on NO release, these labdane derivatives also inhibited prostaglandin E-2 (PGE(2)) production. However, analysis of cell viability demonstrated that effects on NO release and (PGE(2)) production of compounds 1, 8 and 9 were due to citotoxicity, whereas compound 2 and 5 did not show any effect in the survival of RAW 264.7 macrophages. In addition to these in vitro data, compound 5 also showed anti-inflammatory activity in vivo, when tested in mice. They prevented the extent of swelling in the TPA-induced ear edema model and inhibited MPO activity, showing similar potency to that of the widely used anti-inflammatory drug indomethacin. These results indicate that compound 2 and in particular compound 5 might be used for the design of new anti-inflammatory agents. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.007

文献信息

• Stereoselective total synthesis of (.+-.)-eperuane-8.BETA.,15-diol and (.+-.)-labdane-8.ALPHA.,15-diol.
  作者：Toshio Nakamura、Hiroshi Hirota、Takeyoshi Takahashi

  DOI：10.1248/cpb.34.3518

  日期：——

  (±)-Eperuane-8β, 15-diol (5__∼) and (±)-labdane-8α, 15-diol (6__∼), diastereomeric diterpenes to each other, were synthesized stereoselectively, via the same intermediate lactone (7__∼) starting from a known racemic tricyclic compound (8__∼).

  (±)-Eperuane-8β, 15-diol(5__∼)和(±)-labdane-8α, 15-diol(6__∼)是互为非对映异构体的二萜类化合物，它们是由已知的外消旋三环化合物(8__∼)通过相同的中间内酯(7__∼)立体选择性合成的。
• Stereoselective Total Synthesis of (±)-Labdane-8α,15-diol and (±)-Eperuane-8β,15-diol
  作者：Hiroshi Hirota、Toshio Nakamura、Takahiko Tsuyuki、Takeyoshi Takahashi

  DOI：10.1246/bcsj.61.4023

  日期：1988.11

  (±)-Labdane-8α,15-diol and (±)-eperuane-8β,15-diol, diastereomeric diterpenes to each other, were prepared separately and stereoselectively, via a common 7-membered lactone from the known tricyclic keto alcohol.

  (±)-莱布丹-8α,15-二醇和(±)-eperuane-8β,15-二醇是互为非对映异构体的二萜类化合物，它们分别通过已知的三环酮醇中的一个共同的 7 元内酯立体选择性地制备出来。
• Dorta, Rosa L.; Francisco, Cosme G.; Hernandez, Rosendo, Journal of Chemical Research, Miniprint, 1990, # 8, p. 1836 - 1854
  作者：Dorta, Rosa L.、Francisco, Cosme G.、Hernandez, Rosendo、Salazar, Jose A.、Suarez, Ernesto

  DOI：——

  日期：——
• DORTA, ROSA L.;FRANCISCO, COSME G.;HERNANDEZ, ROSENDO;SALAZAR, JOSE A.;SU+, J. CHEM. RES. MICROFICHE.,(1990) N8, C. 240-241
  作者：DORTA, ROSA L.、FRANCISCO, COSME G.、HERNANDEZ, ROSENDO、SALAZAR, JOSE A.、SU+

  DOI：——

  日期：——
• HIROTA, HIROSHI;NAKAMURA, TOSHIO;TSUYUKI, TAKAHIKO;TAKAHASHI, TAKEYOSHI, BULL. CHEM. SOC. JAP., 61,(1988) N1, C. 4023-4028
  作者：HIROTA, HIROSHI、NAKAMURA, TOSHIO、TSUYUKI, TAKAHIKO、TAKAHASHI, TAKEYOSHI

  DOI：——

  日期：——