methyl (5S,8R,9R,10S,13S)-8-hydroxylabdan-15-oate | 10267-25-1

• 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: methyl (5S,8R,9R,10S,13S)-8-hydroxylabdan-15-oate
• 英文别名: methyl 8α-hydroxylabdan-15-oate；methyl labdanolate；(13S)-8-hydroxy-labdan-15-oic acid methyl ester；(13S)-8-Hydroxy-labdan-15-saeure-methylester；(13S)-8α-Hydroxy-labdan-15-saeure-methylester, Epilabdanolsaeuremethylester；(8R,13S)-8-Hydroxy-labdan-16-saeure-methylester；methyl (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-methylpentanoate
• CAS: 10267-25-1
• 化学式: C₂₁H₃₈O₃
• 分子量: 338.531
• InChiKey: GOECIRGMYVJNBS-CFPPRVJZSA-N

物化性质

• 熔点：
  71-73 °C(Solv: ligroine (8032-32-4))
• 沸点：
  403.9±18.0 °C(Predicted)
• 密度：
  0.964±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  methyl (5S,8R,9R,10S,13S)-8-hydroxylabdan-15-oate 在 吡啶 、 溶剂黄146 、 铂 、 三氯氧磷 作用下， 生成 (13S)-labdan-15-oic acid methyl ester
  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
• 作为产物：
  描述：

  8-hydroxy-15,16-dinor-labdan-13-one 在 乙醚 、 乙醇 、 magnesium,ethynoxyethane,bromide 、 铂 、 苯 作用下， 生成 methyl (5S,8R,9R,10S,13S)-8-hydroxylabdan-15-oate
  参考文献：
  名称：

  893.二萜的合成。第三部分 拉丹烷基二萜的合成和在13位的构型

  摘要：

  DOI：

  10.1039/jr9600004613

文献信息

• Regioselective dehydration of axial and equatorial tertiary alcohols with α-methyl group in the cyclohexane ring by Swern’s reagent
  作者：P. F. Vlad、N. D. Ungur、A. N. Aricu、I. Yu. Andreeva

  DOI：10.1007/bf02495210

  日期：1997.4

  oxalyl chloride with DMSO) was shown to dehydrate tertiary alcohols containing an α-methyl group in the cyclohexane ring. Dehydration of equatorial alcohols affords mixtures of isomeric compounds where isomers with an exocyclic double bond dominate, whereas isomers with an endocyclic double bond prevail in the products of dehydration of axial tertiary alcohols. Thus, Swern’s reagent can serve as a chemical

  Swern's 试剂（草酰氯与 DMSO 的复合物）被证明可以使环己烷环中含有 α-甲基的叔醇脱水。赤道醇的脱水提供异构化合物的混合物，其中具有环外双键的异构体占主导地位，而具有环内双键的异构体在轴向叔醇的脱水产物中占优势。因此，Swern's 试剂可以作为化学测试来确定在环己烷环中含有 α-甲基的叔醇的构型。这些醇用 Swern 试剂脱水的产物的组成类似于它们在吡啶中用 POCl3 脱水得到的产物。
• Turkish tobacco—I
  作者：J.A. Giles、J.N. Schumacher

  DOI：10.1016/s0040-4020(01)92174-x

  日期：1961.1

  Two hitherto unknown diterpene lactones have been isolated from Turkish tobacco. Characterization studies show that these compounds, now called α- and β-levantenolides, are represented by I and II. The levantenolides differ only in being epimeric at C12, and are closely related to labdanolic acid.

  从土耳其烟草中分离出了两种迄今未知的二萜内酯。表征研究表明，这些化合物（现在称为α-和β-左旋烯内酯）以I和II表示。黎万特内酯的区别仅在于在C 12上是差向异构体，并且与拉丹酸密切相关。
• 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：——
• Vlad,P.F.; Russo,A.G., Journal of general chemistry of the USSR, 1971, vol. 41, p. 226 - 227
  作者：Vlad,P.F.、Russo,A.G.

  DOI：——

  日期：——
• 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.