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3β-hydroxycopalic acid | 872979-45-8

中文名称
——
中文别名
——
英文名称
3β-hydroxycopalic acid
英文别名
3Beta-Hydroxycopalic Acid;(E)-5-[(1R,4aS,6S,8aS)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid
3β-hydroxycopalic acid化学式
CAS
872979-45-8
化学式
C20H32O3
mdl
——
分子量
320.472
InChiKey
LNWOKEZJIRLIDO-FCFWMCEOSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    4.7
  • 重原子数:
    23
  • 可旋转键数:
    4
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.75
  • 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:
    3β-hydroxycopalic acid 在 palladium on activated charcoal 、 氢气 作用下, 以 乙醇 为溶剂, 20.0 ℃ 、202.66 kPa 条件下, 反应 2.0h, 以85%的产率得到
    参考文献:
    名称:
    Antitubercular Activity Increase in Labdane Diterpenes from Copaifera Oleoresin through Structural Modification
    摘要:
    The labdane diterpenes copalic acid, 3 beta-acetoxy-copalic acid, 3 beta-hydroxy-copalic acid and ent-agathic acid were isolated from Copaifera langsdorffii oleoresin. These four compounds were submitted to structural modifications by reduction with hydrogen/palladium, esterification with diazomethane, esterification with methanol/sulfuric acid and conversion into sodium salt, furnishing 15 compounds. All compounds were assayed in vitro against Mycobacterium tuberculosis (H37Rv, ATCC 27294). The four compounds displayed minimum inhibitory concentration (MIC) value of 125 mu g mL(-1), and were not considered active. A methylated derivative of compound 3 beta-hydroxy-copalic acid, and a sodium salt of copalic acid displayed MIC values of 25 mu g mL(-1) (71.7 mu M) and 6.25 mu g mL(-1) (19.2 mu M), respectively. The sodium salt of copalic acid stood out by displaying similar activity in comparison with streptomycin (MIC 6.25 mu g mL(-1)) and a better activity compared to mu M value of pyrazinamide (MIC 3.12 mu g mL(-1); 25.34 mu M). Therefore, the methylated derivative of compound 3 beta-hydroxy-copalic acid and the sodium salt of copalic acid should be considered for further studies.
    DOI:
    10.21577/0103-5053.20160268
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文献信息

  • Antitubercular Activity Increase in Labdane Diterpenes from Copaifera Oleoresin through Structural Modification
    作者:Aline Silva、Ana Carolina Soares、Mirela Cabral、Alex de Andrade、Marilza da Silva、Carlos Martins、Rodrigo Veneziani、Sérgio Ambrósio、Jairo Bastos、Vladimir Heleno
    DOI:10.21577/0103-5053.20160268
    日期:——
    The labdane diterpenes copalic acid, 3 beta-acetoxy-copalic acid, 3 beta-hydroxy-copalic acid and ent-agathic acid were isolated from Copaifera langsdorffii oleoresin. These four compounds were submitted to structural modifications by reduction with hydrogen/palladium, esterification with diazomethane, esterification with methanol/sulfuric acid and conversion into sodium salt, furnishing 15 compounds. All compounds were assayed in vitro against Mycobacterium tuberculosis (H37Rv, ATCC 27294). The four compounds displayed minimum inhibitory concentration (MIC) value of 125 mu g mL(-1), and were not considered active. A methylated derivative of compound 3 beta-hydroxy-copalic acid, and a sodium salt of copalic acid displayed MIC values of 25 mu g mL(-1) (71.7 mu M) and 6.25 mu g mL(-1) (19.2 mu M), respectively. The sodium salt of copalic acid stood out by displaying similar activity in comparison with streptomycin (MIC 6.25 mu g mL(-1)) and a better activity compared to mu M value of pyrazinamide (MIC 3.12 mu g mL(-1); 25.34 mu M). Therefore, the methylated derivative of compound 3 beta-hydroxy-copalic acid and the sodium salt of copalic acid should be considered for further studies.
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同类化合物

(5β,6α,8α,10α,13α)-6-羟基-15-氧代黄-9(11),16-二烯-18-油酸 (3S,3aR,8aR)-3,8a-二羟基-5-异丙基-3,8-二甲基-2,3,3a,4,5,8a-六氢-1H-天青-6-酮 (2Z)-2-(羟甲基)丁-2-烯酸乙酯 (2S,4aR,6aR,7R,9S,10aS,10bR)-甲基9-(苯甲酰氧基)-2-(呋喃-3-基)-十二烷基-6a,10b-二甲基-4,10-dioxo-1H-苯并[f]异亚甲基-7-羧酸盐 (+)顺式,反式-脱落酸-d6 龙舌兰皂苷乙酯 龙脑香醇酮 龙脑烯醛 龙脑7-O-[Β-D-呋喃芹菜糖基-(1→6)]-Β-D-吡喃葡萄糖苷 龙牙楤木皂甙VII 龙吉甙元 齿孔醇 齐墩果醛 齐墩果酸苄酯 齐墩果酸甲酯 齐墩果酸乙酯 齐墩果酸3-O-alpha-L-吡喃鼠李糖基(1-3)-beta-D-吡喃木糖基(1-3)-alpha-L-吡喃鼠李糖基(1-2)-alpha-L-阿拉伯糖吡喃糖苷 齐墩果酸 beta-D-葡萄糖酯 齐墩果酸 beta-D-吡喃葡萄糖基酯 齐墩果酸 3-乙酸酯 齐墩果酸 3-O-beta-D-葡吡喃糖基 (1→2)-alpha-L-吡喃阿拉伯糖苷 齐墩果酸 齐墩果-12-烯-3b,6b-二醇 齐墩果-12-烯-3,24-二醇 齐墩果-12-烯-3,21,23-三醇,(3b,4b,21a)-(9CI) 齐墩果-12-烯-3,11-二酮 齐墩果-12-烯-2α,3β,28-三醇 齐墩果-12-烯-29-酸,3,22-二羟基-11-羰基-,g-内酯,(3b,20b,22b)- 齐墩果-12-烯-28-酸,3-[(6-脱氧-4-O-b-D-吡喃木糖基-a-L-吡喃鼠李糖基)氧代]-,(3b)-(9CI) 鼠特灵 鼠尾草酸醌 鼠尾草酸 鼠尾草酚酮 鼠尾草苦内脂 黑蚁素 黑蔓醇酯B 黑蔓醇酯A 黑蔓酮酯D 黑海常春藤皂苷A1 黑檀醇 黑果茜草萜 B 黑五味子酸 黏黴酮 黏帚霉酸 黄黄质 黄钟花醌 黄质醛 黄褐毛忍冬皂苷A 黄蝉花素 黄蝉花定