Daphnetin 7,8-二羟基-2H苯并吡喃-2-酮

CAS 486-35-1 MFCD00016977

化学结构图

486-35-1
SMILES: O=c1ccc2ccc(O)c(O)c2o1

化学属性

Mol. FormulaC9H6O4
Mol. Weight178.143
Appearance solid
Melting Point265-268°C
Boiling Point430.4°C at 760 mmHg

别名和识别编码

Chemical NameDaphnetin
CAS Number486-35-1
Alfabeta NameDIHYDROXYCHROMENONE 782---,
MDL NumberMFCD00016977
Synonym Daphnetin {LY} Daphnetin {} {LY} Daphnetin {} {} {LY} Daphnetin {} {} {} {LY} Daphnetin {} {} {} {} {Chemicalbook} Daphenetin {} {} {} {} {} {Chemicalbook} DAPHNETIN(P) {} {} {} {} {} {} {Chemicalbook} AKOS 213-37 {} {} {} {} {} {} {} {Chemicalbook} 7,8-二羥香豆素 {} {} {} {} {} {} {} {} {PubChem} 7,8-dihydroxycoumarin {} {} {} {} {} {} {} {} {} {Chemicalbook} 7,8-dihydroxy-coumari {} {} {} {} {} {} {} {} {} {} {Chemicalbook} 7,8-dihydroxy-2h-1-benzopyran-2-on {} {} {} {} {} {} {} {} {} {} {} {Chemicalbook} 7,8-Diydroxycoumarin {} {} {} {} {} {} {} {} {} {} {} {} {JNK} 7,8-Dihydroxycoumarin {} {} {} {} {} {} {} {} {} {} {} {} {} {Chemicalbook} 7,8-DIHYDROXYCOUMARIN (DAPHNETIN) {} {} {} {} {} {} {} {} {} {} {} {} {} {} {hazard_com} 2H-1-Benzopyran-2-one, 7,8-dihydroxy- {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {Chemicalbook} (白)瑞香素 {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {
PubChem Substance ID5280569
EC Number207-632-8
Chemical Name Translation7,8-二羟基-2H苯并吡喃-2-酮
Beilstein Registry Number9372
Reaxys-RN9372
Merck Number2817
LabNetwork Molecule IDLN00170034
InChIInChI=1S/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H
Canonical SMILESO=C1C=CC2=CC=C(O)C(O)=C2O1
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分类

  • {SNA} Bioactive Small Molecule Alphabetical Index,
  • {SNA} Bioactive Small Molecule Alphabetical Index, DIG-DY, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Fluorescent Labels, Kinase/Phosphatase Biology, Other Fluorescent Labels, P to Q,
  • {SNA} Bioactive Small Molecule Alphabetical Index, Biochemicals and Reagents, DIG-DY, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Fluorescent Labels, Fluorescent Probes, Labels, Particles and Stains, Kinase/Phosphatase Biology, Other Fluorescent Labels, P to Q, Protein Kinase Inhibitors, Protein Kinases (PK), Protein kinase, tyrosine, EGF receptor, Serine/Threonine Kinase Biology, Serine/Threonine Kinase Inhibitors,

相关文献及参考

  • Yang, Y.Z., et al., Daphnetin: a novel antimalarial agent with in vitro and in vivo activity. Am. J. Trop. Med. Hyg. 46 , 15, (1992) 摘要
  • Yang, E.B., et al., Daphnetin, one of coumarin derivatives, is a protein kinase inhibitor. Biochem. Biophys. Res. Commun. 260 , 682, (1999) 摘要
  • Merck 14 ,2817

安全信息

Warnings IRRITANT
WGK Germany2
RTECSGN6382600
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘;
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
Risk Statements
  • R20/21 Harmful by inhalation and in contact with skin 吸入及与皮肤接触有害
GHS Symbol
Signal word Warning
Precautionary statements
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P302+P350
  • P302+P352
  • P302+P352+P332+P313+P362+P364
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P321 Specific treatment (see … on this label). 具体治疗(见本标签上的)。
  • P332+P313
  • P337+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
Storage condition 2-8°C {LY} 2-8°C {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {TCI} 0-10°C
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 429 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book
   Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23,    1978-88. For
   publisher information, see ZYZAEU.  Volume(issue)/page/year: 22,87,1987

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 375 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book
   Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23,    1978-88. For
   publisher information, see ZYZAEU.  Volume(issue)/page/year: 22,87,1987

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 5370 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book
   Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23,    1978-88. For
   publisher information, see ZYZAEU.  Volume(issue)/page/year: 22,87,1987

其他信息

  • 瑞香提取物:瑞香素是由瑞香科瑞香属植物长白瑞香中提取出来的有效成分,现已人工合成,试验表明瑞香素具有扩张冠状血管、增加冠脉流量、减少心肌耗氧量,改善心肌代谢、促进心功能恢复及抗血栓形成等作用。临床可用于心绞痛、冠心病、血栓闭塞性脉管炎等。也可用于风湿性关节炎,因还具有一定抗炎、镇痛作用。口服:1次450mg,1日3次。用药后偶有胃肠道反应。有出血倾向的患者及孕妇慎用。
  • 抗疑作用:白瑞香甙给家兔口服30~50mg/kg,可降低血液凝固性,作用最强在第2~3天,并持续1~3天。
  • 现代应用:现代临床用之治疗坐骨神经痛。采新鲜雪冻花烘干研粉,装入胶囊,每粒0.4克;另用碘化钾,亦装入胶囊,每粒0.6克(临服时装入)。服法:雪冻花胶囊2粒,碘化钾胶囊3粒为1剂,分3次服完。即第1晚服雪冻花胶囊1粒,第2晚服碘化钾胶囊2粒,第3晚服雪冻花,碘化钾胶囊各1粒。连服2剂为1疗程。若服1疗程无效者即停药; 病程长者可服2疗程。 其它:含多量伞形花内酯。白瑞香甙给家兔口服30~50毫克/公斤时,可降低 血液粘稠度,作用最强在第2~3天,并持续1~3天。并使血液对肝素的耐受性降低,第Ⅱ,Ⅶ,Ⅹ因子活性下降。血块弹力图上显示反应时间及血块形成延长。此种作用可被维生素K拮抗。白瑞香甙还能促进体内尿酸排泄。
  • 原植物:植物形态:常绿直立灌木;枝粗壮,通常二歧分枝,小枝近圆柱形,紫红色或紫褐色,无毛。叶互生,纸质,长圆形或倒卵状椭圆形,长7-13厘米,宽2.5-5厘米,先端钝尖,基部楔形,边缘全缘,上面绿色,下面淡绿色,两面无毛,侧脉7-13对,与中脉在两面均明显隆起;叶柄粗壮,长4-10毫米,散生极少的微柔毛或无毛。 花外面淡紫红色,内面肉红色,无毛,数朵至12朵组成顶生头状花序;苞片披针形或卵状披针形,长5-8毫米,宽2-3毫米,无毛,脉纹显著隆起;花萼筒管状,长6-10毫米,无毛,裂片4,心状卵形或卵状披针形,基部心脏形,与花萼筒等长或超过之;雄蕊8,2轮,下轮雄蕊着生于花萼筒中部以上,上轮雄蕊的花药1/2伸出花萼筒的喉部,花丝长0.7毫米,花药长圆形,长2毫米;子房长圆形,无毛,顶端钝形,花柱短,柱头头状。果实红色。花期3-5月,果期7-8月。 生长习性:性喜半阴和通风环境,惧暴晒,不耐积旱。 植物分布:瑞香原产福建省武夷山市慧苑岩,现在长江流域以南都有栽培。 图1为瑞香花图片。
  • 药性:性味:①江西《草药手册》:“甘,咸。” ②《新华本草纲要》:“苦、辛,温。”。 功效:祛风除湿,活血止血。 主治:①《药性考》:“清利头目,齿痛宜含。” ②《纲目拾遗》:“稀痘,治乳岩初起。” ③《新华本草纲要》:“风湿性关节炎,坐骨神经疼,牙疼,咽喉疼,跌打损伤,初起乳腺癌及疮疡”。 用法用量:内服:煎汤,3~6g。外用:捣敷或煎水含漱。 使用注意:江西《中草药手册》:“本品有麻醉性,内服宜慎。”
  • MOL 文件:486-35-1.mol
  • Sigma Aldrich:486-35-1(sigmaaldrich)
  • 化学成分:①瑞香全草含瑞香甙[Daphnin,即白瑞香甙,也即白瑞香素(瑞香素)-7-葡萄糖甙,Daphnetin-7-glucoside]约2%~4%、白瑞香素(瑞香素)-8-葡萄糖甙等;且含多量伞形花内酯(7-羟基香豆素,Um-belliferone)等。 ②作“祖师麻”药源之一的同属植物唐古特瑞香(D.tangutica Maxim.):茎皮中含绣球亭(Hydragetin)、7-羟基香豆素(Umbelliferone)、西瑞香素(Daphnoretin)、瑞香素(Daphnetin)、大黄素甲醚(Physcion)、7-甲氧基-8-羟基香豆素、瑞香甙(Daphnin)、β-谷甾醇、三硬脂酸甘油酸、α-香树脂醇醋酸酯等;根中含:木脂素类:松脂素(Pinoresinol)、(-)-落叶松脂素[(-)-Lari-ciresinol ]、(-)-二氢芝麻脂素[(-)-Dihydrosesamin ]、(±)-丁香脂素[(±)-Sy-ringaresinol]等,香豆素类:瑞香素(Daphnetin)、7-羟基-8-甲氧基香豆素(Hydragetin)、西瑞香素(Daph-noretin)、瑞香辛(Daphneticin)等,另外尚含瑞香醇酮(Daphneolone)及二萜酯类化合物格尼迪春(Gni-ditrin)等。

系列性分类


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