Osthole 蛇床子素

CAS 484-12-8 MFCD00076049

化学结构图

484-12-8
SMILES: COc1ccc2ccc(=O)oc2c1CC=C(C)C

化学属性

Mol. FormulaC15H16O3
Mol. Weight244.29
Melting Point83-84°C
Density1.126
Boiling Point396.7°C at 760 mmHg

别名和识别编码

Chemical NameOsthole
CAS Number484-12-8
Alfabeta NameMETHOXYMETHYLBUTENYLCHROMENONE H7832122()------------
MDL NumberMFCD00076049
Synonym Osthole {Chemicalbook} 7-Methoxy-8-(3-methyl-2-butenyl)-2H-chromen-2-one 7-Methoxy-8-(3-methyl-2-butenyl)-coumarin 7-Methoxy-8-(3-methyl-2-butenyl)coumarin 7-Methoxy-8-(3-methyl-2-butenyl)coumarin 7-Methoxy-8-isopentenylcoumarin Osthol 7-Methoxy-8-isopentenylcoumarin 7-甲氧基-8-异戊烯基香豆素 8-(3-METHYL-2-BUTENYL)HERNIARIN Cnidium lactone(OSTHOLE ) OSTHOL Osthol {} {Chemblink} 7-Methoxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one {} {} {Chemicalbook} 7-METHOXY-8-(3-METHYL-BUT-2-ENYL)-CHROMEN-2-ONE {} {} {} {} {} {} {} {} {Chemicalbook {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
Chemical Name Translation蛇床子素
Reaxys-RN1288399
Merck Number6895
PubChem Substance ID10228
EC Number610-421-7
Wiswesser Line NotationT66 BOVJ IO1 J2UY1&1
LabNetwork Molecule IDLN00173575
InChIInChI=1S/C15H16O3/c1-10(2)4-7-12-13(17-3)8-5-11-6-9-14(16)18-15(11)12/h4-6,8-9H,7H2,1-3H3
Canonical SMILESO=C1C=CC2=CC=C(OC)C(C/C=C(C)\C)=C2O1
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分类

  • {SNA} Fatty Acid Synthase (FAS) Inhibitors, Metabolites, Inhibitors and Activators of Fatty Acid Metabolism, Phenols, Phytochemicals by Chemical Classification, 癌症代谢, 癌症发生过程中的脂肪酸代谢, 癌症研究, 细胞生物学, 营养研究
  • {SNA} Cancer Metabolism, Cancer Research, Fatty Acid Metabolism in Oncogenesis,

产品应用

  • 具有解痉、降血压、抗心律失常、增强免疫功能及广谱抗菌作用。

相关文献及参考

  • [2]. Tang DZ, et al. Osthole stimulates osteoblast differentiation and bone formation by activation of beta-catenin-BMP signaling. J Bone Miner Res. 2010 Jun;25(6):1234-45.
  • [3]. Sun W, et al. Osthole pretreatment alleviates TNBS-induced colitis in mice via both cAMP/PKA-dependent and independent pathways. Acta Pharmacol Sin. 2017 Aug;38(8):1120-1128.
  • [4]. Zhang ZR, et al. Osthole: A Review on Its Bioactivities, Pharmacological Properties, and Potential as Alternative Medicine. Evid Based Complement Alternat Med. 2015;2015:919616.
  • Merck: 14,6895
  • [1]. Kordulewska NK, et al. Changes in gene expression induced by histamine, fexofenadine and osthole: Expression of histamine H1 receptor
  • [1]. Kordulewska NK, et al. Changes in gene expression induced by histamine, fexofenadine and osthole: Expression of histamine H1 receptor, COX-2, NF-κB, CCR1, chemokine CCL5/RANTES and interleukin-1β in PBMC allergic and non-allergic patients. Immunobiology.

安全信息

Warnings IRRITANT
RTECSGN7700000
WGK Germany3
Storage condition 2-8°C {LY} 2-8°C {} {LY} -20℃ {} {} {LY} -20°C 室温保存
Signal word Warning
Precautionary statements
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛,皮肤或衣服。
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适,呼叫解毒中心或医生/医师。
Hazard statements
  • H303 May be harmfully swallowed 吞食可能有害
GHS Symbol
TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 25 mg/kg
TOXIC EFFECTS :
   Behavioral - convulsions or effect on seizure threshold
   Lungs, Thorax, or Respiration - respiratory stimulation
   Lungs, Thorax, or Respiration - other changes
REFERENCE :
   AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans
   Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium)  V.4-   
   1898-  Volume(issue)/page/year: 138,400,1962

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 2905 mg/kg
TOXIC EFFECTS :
   Behavioral - convulsions or effect on seizure threshold
   Behavioral - muscle contraction or spasticity
   Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
   IJMRAQ Indian Journal of Medical Research.  (Indian Council of Medical
   Research, Ansari Nagar, New Delhi 110 029, India)  V.1-    1913-
   Volume(issue)/page/year: 55,241,1967

TYPE OF TEST            : LD - Lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Mammal - dog
DOSE/DURATION           : >40 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans
   Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium)  V.4-   
   1898-  Volume(issue)/page/year: 150,425,1964

TYPE OF TEST            : LD - Lethal dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : >70 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans

其他信息

  • 植物提取物:蛇床子素是从伞形科一年生草本植物蛇床子的果实中提取出来的一种物质,外观为黄绿色至白色结晶粉末,不溶于水和冷石油醚,易溶于丙酮、甲醇、乙醇、氯仿、三氯甲烷、乙酸乙酯,可溶于沸的石油醚,具有解痉、降血压、抗心律失常、增强免疫功能及广谱抗菌作用。临床上主要用于治疗男子阳痿、阴囊湿痒、女子带下阴痒、子宫寒冷不孕、风湿痹痛、疥癣湿疮、滴虫性阴道炎。蛇床子素还可用做大田杀虫剂、杀菌剂,以触杀作用为主,胃毒作用为辅,药液通过体表吸收进入昆虫体内,作用于害虫神经系统,导致害虫肌肉非功能性收缩,最终衰竭而死,对多种害虫如菜青虫、茶尺蠖、棉铃虫、甜菜夜蛾以及各种蚜虫有较好的触杀效果。
  • 药理作用:蛇床子素具有解痉、降血压、抗心律失常、增强免疫功能及广谱抗菌作用。蛇床子素不仅具有抗高血压、抗心律失常、抗炎、抗肿瘤、抗骨质疏松症等功效,而且作为一种新型的生物农药对害虫、植物病原菌亦有显著作用。
  • 属香豆素类化合物。棱柱状结晶(乙醚)、针状结晶(稀乙醇)。溶于碱溶液、乙醇、氯仿、丙酮等,不溶于水和石油醚。
  • MOL 文件:484-12-8.mol
  • 用途一:具有解痉、降血压、抗心律失常、增强免疫功能及广谱抗菌作用。
  • 植物源杀虫剂:蛇床子素是一类最先从伞形科植物中提取分离出的天然香豆素类化合物,伞形科植物蛇床的干燥成熟果实蛇床子(Fructus cnidii)中含量较高,故而得名。相关研究表明蛇床子素还存在于其他多种植物,主要包括当归属、古当归属、蛇床属等伞形科植物以及柑橘属、黄皮属、象橘属、拟芸香属等芸香科植物,另外在菊科和豆科少数种中也有分布。 蛇床子素又名甲氧基欧芹酚或欧芹酚甲醚(osthole,Ost),其化学名称为7-甲氧基-8-异戊烯基香豆素,核心结构由苯环和吡喃酮环组成。作为香豆索类化合物的一员,蛇床子素除具有香豆素的核心结构外,还有异戊烯结构,异戊烯结构化合物作为植保素在抗病中具有重要作用。 蛇床子素为植物源杀虫剂,其作用方式以触杀作用为主,胃毒作用为辅,药液通过体表吸收进入昆虫体内,作用于害虫神经系统,导致害虫肌肉非功能性收缩,最终衰竭而死。经室内活性毒力测定试验表明,对菜青虫有较高的活性(LD50为6.2258mg/kg)。经田间药效试验表明,对十字花科蔬菜菜青虫和茶树茶尺蠖有较好的防效。防治十字花科蔬菜菜青虫用药量为有效成分4.8~7.2g/h㎡(折成0.4%蛇床子素乳油商品量每亩地用80~120mL);防治茶树蠖用药量为有效成分6~7.2g/h㎡(折成0.4%蛇床子素乳油商品量每亩地用100~120mL)。一般每亩用药液量为50~75kg,均匀喷雾;持效期为7d左右。在用药剂量范围内对作物安全,未见药害。
  • 外观性质:属香豆素类化合物。棱柱状结晶(乙醚)、针状结晶(稀乙醇)。溶于碱溶液、乙醇、氯仿、丙酮等,不溶于水和石油醚。熔点:83~84℃沸点:145~150℃
  • 理化性质:蛇床子素属香豆素类化合物。棱柱状结晶(乙醚)、针状结晶(稀乙醇),熔点83~84℃,沸点145~150℃,溶于碱溶液、甲醇、乙醇、氯仿、丙酮、醋酸乙酯和沸石油醚等,不溶于水和石油醚。
  • Sigma Aldrich:484-12-8(sigmaaldrich)

系列性分类


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