13(S)-labdan-8α,15-diol | 10267-21-7

• 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: 13(S)-labdan-8α,15-diol
• 英文别名: (8R,13S)-labdan-8,15-diol；labdane-8α,15-diol；8,15-labdanediol；Labdanediol；(13S)-labdane-8,15-diol；(13S)-Labdan-8,15-diol；(1R,2R,4aS,8aS)-1-[(3S)-5-hydroxy-3-methylpentyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
• CAS: 10267-21-7
• 化学式: C₂₀H₃₈O₂
• 分子量: 310.521
• InChiKey: MCHQEVJMCLOQAZ-VBYALHQYSA-N

物化性质

• 熔点：
  84-85 °C
• 沸点：
  180-182 °C(Press: 0.2 Torr)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  13(S)-labdan-8α,15-diol 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(3S)-3-methyl-5-[(1R,2S)-1,2,5,5-tetramethyl-2,3,4,6,7,8-hexahydronaphthalen-1-yl]pentan-1-ol
  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
• 作为产物：
  描述：

  methyl (5S,8R,9R,10S,13S)-8-hydroxylabdan-15-oate 在 lithium aluminium tetrahydride 作用下， 生成 13(S)-labdan-8α,15-diol
  参考文献：
  名称：

  Vlad,P.F.; Russo,A.G., Journal of general chemistry of the USSR, 1971, vol. 41, p. 226 - 227

  摘要：

  DOI：

文献信息

• Hemisynthesis and Bactericidal Activity of Several Substituted Benzoic Acid Esters of 13(S)-Labdan-8α,15-Diol, a Diterpene from Oxylobus glanduliferus
  作者：Pablo A. Chacon-Morales、Juan M. Amaro-Luis、Luis B. Rojas Fermin、Nurby N. Rios Tesch、Maria E. Lucena Escalona、Miguel A. Rodriguez Pena、Philippe A. Peixoto、Remi Jacquet、Denis Deffieux、Laurent Pouysegu、Stephane Quideau

  DOI：10.1007/s10600-019-02777-6

  日期：2019.7

  15-diol (1) was isolated in high yield from Oxylobus glanduliferus, a native species of Venezuelan Andean moorlands. Using this compound (1) as a starting material, it was possible to prepare 12 aromatic esters, which were structurally characterized by analysis of their spectroscopic data (IR, 1D and 2D NMR and MS). The bactericidal activity of these diterpene derivatives was evaluated against four bacterial

  二萜 13(S)-labdan-8α,15-diol (1) 是从委内瑞拉安第斯高地的原生物种 Oxylobusgluliferus 中以高产分离出来的。使用该化合物 (1) 作为起始原料，可以制备 12 种芳族酯，通过分析它们的光谱数据 (IR、1D 和 2D NMR 和 MS) 对其进行结构表征。针对四种细菌菌株 [两种革兰氏阳性和两种革兰氏阴性] 评估了这些二萜衍生物的杀菌活性：金黄色葡萄球菌、粪肠球菌、大肠杆菌和铜绿假单胞菌。
• Diterpenoids and flavonoids from Cistus palinhae
  作者：J.De Pascual Teresa、J.G. Urones、I.S. Marcos、L. Núñez、P. Basabe

  DOI：10.1016/s0031-9422(00)97701-x

  日期：1983.1

  Abstract Cativic, ladenic, labdanolic, 8α-hydroxy-13( E )-labden-15-oic and 3-phenylpropionic acids were isolated from Cistus palinhae . In addition two new acids were characterized as 8α-methoxy-labd-15-oic and (5 R , 8 R , 9 S , 10 S )-2-oxo-3- cis -cleroden-15-oic. From the neutral fraction were isolated the known 8,15-labdanediol, 8(17)labden-15-ol, 6-oxo-7-labden-15-ol and 6β-hydroxy-8(17)-labden-15-ol

  摘要 从岩蔷薇中分离得到Cativic、ladenic、labdanolic、8α-hydroxy-13(E)-labden-15-oic和3-苯基丙酸。此外，两种新的酸被表征为 8α-甲氧基-labd-15-oic 和 (5 R , 8 R , 9 S , 10 S )-2-oxo-3-cis -cleroden-15-oic。从中性馏分中分离出已知的 8,15-labdanediol、8(17)labden-15-ol、6-oxo-7-labden-15-ol 和 6β-hydroxy-8(17)-labden-15-ol还鉴定了羟基衍生物 8α-羟基-15-苯基丙氧基-劳丹烷、8α-羟基-15-乙酰氧基-劳丹烷、8-labden-15-ol 和 8-epi -15-labdanediol。弱酸部分得到 jaranol（5,4'-二羟基-3,7-二甲氧基黄酮）、genkwanin（5,
• 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。
• METHOD FOR SYNTHESISING AMBROXIDE FROM AGERATINA JOCOTEPECANA
  申请人：UNIVERSIDAD MICHOACANA DE SAN NICOLÁS DE HIDALGOú

  公开号：US20190023679A1

  公开（公告）日：2019-01-24

  The present invention is related to a process for obtaining the (−)-13,14,15,16-tetranor-8a,12-labdanediol compound from the Ageratina jocotepecana plant, the process comprises the steps of a) obtaining an organic concentrated extract from the Ageratina jocotepecana shoot system; b) subjecting the organic concentrated extract to column chromatography in order to elute a fraction with the (−)-13,14,15,16-tetranor-8a,12-labdanediol compound; c) separating the eluted fractions comprising the (−)-13,14,15,16-tetranor-8a,12-labdanediol compound; and d) evaporating the organic solvent to yield the (−)-13,14,15,16-tetranor-8a,12-labdanediol compound in a solid form.

  本发明涉及一种从Ageratina jocotepecana植物中获取(−)-13,14,15,16-四去甲基-8a,12-拉丹二醇化合物的方法，包括以下步骤：a)从Ageratina jocotepecana茎系统中提取有机浓缩物；b)将有机浓缩物经过柱层析以洗脱出含有(−)-13,14,15,16-四去甲基-8a,12-拉丹二醇化合物的分离物；c)分离含有(−)-13,14,15,16-四去甲基-8a,12-拉丹二醇化合物的洗脱分离物；d)蒸发有机溶剂以得到以固体形式存在的(−)-13,14,15,16-四去甲基-8a,12-拉丹二醇化合物。