8-hydroxy-15-acetoxy-labdane | 89984-13-4

• 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: 8-hydroxy-15-acetoxy-labdane
• 英文别名: 15-Acetoxy-8-hydroxylabdanol；15-O-acetyl-8α-hydroxylabdane；labdan-8α-ol-15-yl acetate；labdan-8α-ol-15-acetate；(13S)-15-acetoxy-labdan-8-ol；[(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-methylpentyl] acetate
• CAS: 89984-13-4
• 化学式: C₂₂H₄₀O₃
• 分子量: 352.558
• InChiKey: NZKLGQRMNDHSPV-DTTOWAHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-hydroxy-15-acetoxy-labdane 在 lead(IV) acetate 、 甲醇 、 氢氧化钾 、 碘 、 calcium carbonate 作用下， 以 环己烷 为溶剂， 反应 10.0h， 生成 1-[(3aS,7aR)-1-[(3S)-5-hydroxy-3-methylpentyl]-4,4,7a-trimethyl-2,3,3a,5,6,7-hexahydro-1H-inden-2-yl]ethanone
  参考文献：
  名称：

  Chemistry of labdanediol from Cistus ladaniferus, L. synthesis of 12-Nor-ambreinolide and α and β-levantenolides

  摘要：

  Labdanediol, 2. the major component of the neutral part of Cistus ladaniferus L, was transformed into 12-nor-ambreinolide, precursor of ambrox(R), in three steps with an overall yield of 70%. Molecular modelling techniques have been used to determine the stereochemistry of the byproducts of these reactions. The selenylation and elimination reactions of alpha and betalevantanolides, obtained from labdanediol, 2, were used to synthetise alpha and beta-levantenolides.

  DOI：

  10.1016/s0040-4020(01)88343-5
• 作为产物：
  描述：

  methyl (5S,8R,9R,10S,13S)-8-hydroxylabdan-15-oate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 生成 8-hydroxy-15-acetoxy-labdane
  参考文献：
  名称：

  820.劳丹脂的化学。第二部分 亚麻酸的结构

  摘要：

  DOI：

  10.1039/jr9560004262

文献信息

• Evaluation of labdane derivatives as potential anti-inflammatory agents
  作者：Natalia Girón、Elisa Pérez-Sacau、Raquel López-Fontal、Juan M. Amaro-Luis、Sonsoles Hortelano、Ana Estevez-Braun、Beatriz de las Heras

  DOI：10.1016/j.ejmech.2010.04.007

  日期：2010.7

  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.
• 820. The chemistry of gum labdanum. Part II. The structure of labdanolic acid
  作者：J. D. Cocker、T. G. Halsall

  DOI：10.1039/jr9560004262

  日期：——
• Chemistry of labdanediol from Cistus ladaniferus, L. synthesis of 12-Nor-ambreinolide and α and β-levantenolides
  作者：J.G. Urones、P. Basabe、I.S. Marcos、D. Díez Martín、M.J. Sexmero、M.H. Peral、H.B. Broughton

  DOI：10.1016/s0040-4020(01)88343-5

  日期：1992.11

  Labdanediol, 2. the major component of the neutral part of Cistus ladaniferus L, was transformed into 12-nor-ambreinolide, precursor of ambrox(R), in three steps with an overall yield of 70%. Molecular modelling techniques have been used to determine the stereochemistry of the byproducts of these reactions. The selenylation and elimination reactions of alpha and betalevantanolides, obtained from labdanediol, 2, were used to synthetise alpha and beta-levantenolides.