Natural Yellow 18 氯化黄连素水合物

CAS 141433-60-5 MFCD00011939

化学结构图

141433-60-5
SMILES:

化学属性

Mol. FormulaC20H18ClNO4·xH2O
Mol. Weight371.82(as Anhydrous)
Density1.422
Melting Point204-206
Appearance 黄莲素(2086-83-1)是一种常见的异喹啉生物碱。从乙醚中析出者为黄色针状结晶,熔点145℃。溶于水,难溶于苯、乙醚和氯仿。具有季胺盐的特征。其盐类在水中的溶解度都比较小。小檗碱盐酸盐在水中溶解度为1:500。小檗碱盐酸盐又称黄连素,为黄色结晶性粉末。易溶于沸水,微溶于冷水,几乎不溶于冷醇、氯仿和醚。
SolubilitySoluble in DMSO (74 mg/ml at 25 °C), ethanol (<1 mg/ml at 25 °C), water (<1 mg/ml at 25 °C), and methanol.
Stability易吸潮

别名和识别编码

Chemical NameNatural Yellow 18
Synonym BERBERINE CHLORIDE HYDRATE 连黄素氯化物 BERBERINE HYDROCHLORIDE Natural Yellow 18 盐酸小薜碱 水合盐酸小檗碱 小檗碱盐酸盐,BERBERINUMHYDROCHLORIDE InsipBerberine NATURAL YELLOW 18 CHLORIDE 盐酸小檗碱 水合物 小檗碱 {Chemica 黄连素;盐酸黄连素;小檗碱盐酸盐;BBR {Chemi 黄连素 {Ch CI 75160 { 9,10-dimeth BERBERINE HYDROCHLORIDE N-HYDRATE Coptisrootextract 黄莲素盐酸盐水合物 5,6-二氢-9,10-二甲氧基苯并[G]-1,3-二茂苯 BBR 黄连素碱 黄连素盐酸盐 {C 氯化黄连素,97%, 水 <17% LABOTEST-BB LT00440956 BERBERINE CHLORIDE 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)-berbiniuchlori 5,6-二氢-9,10-二甲氧基苯并(G)1,3-苯并二恶茂(5,6-A)喹嗪盐酸盐 BERBERINE 氯化黄连素
Beilstein Registry Number3836585
PubChem Substance ID87563487
MDL NumberMFCD00011939
CAS Number141433-60-5
EC Number211-195-9
Reaxys-RN3836585
Merck Number1154
Chemical Name Translation氯化黄连素水合物
InChIKeyYBHILYKTIRIUTE-UHFFFAOYSA-N
信息真实价格透明    资金保障    专业采购外包团队在线服务   
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分类

  • {SNA} Alkaloid, Cell Biology, Nutrition Research, Phytochemicals by Chemical Classification
  • {SNA} Alkaloid, Anti-Proliferative Agents,
  • {SNA} Alkaloid, Anti-Proliferative Agents, Antitumor Agents, B, Bioactive Small Molecules, Biochemicals and Reagents, Cancer Research, Cell Biology, Cell Signaling and Neuroscience, Drug Efflux Pumps, Drug Transport Compounds, Drug Transport Proteins & Reagents, Membrane Protein Biology Tools, Modulators for MDR/TAP Transporters, Multi-Drug Resistance, Multi-Drug Resistance and Drug Metabolism, Nutrition Research, Phytochemicals by Chemical Classification, Proteins and Derivatives
  • {SNA} Alkaloid,

产品应用

  • 对细菌(主要痢疾、大肠杆菌,金葡球菌)具有微弱的抑制作用,并使细菌体上表面的菌毛数量减少,使细菌不易附着在人体细胞上,能使胃及十二指肠的消化道溃疡减轻。主要用于治疗胃肠炎、细菌性痢疾等肠道感染、腹泻。

相关文献及参考

  • Zhang, X., et al., Degradation Of MDM2 By The Interaction Between Berberine And DAXX Leads To Potent Apoptosis In MDM2-Overexpressing Cancer Cells. Cancer Res. 70 , 9895-904, (2010) 摘要
  • Berlin, G. and Enerback, L. Agents and Actions 14 , 401, (1984)
  • Dimlich, R.V.W., et al. Stain Technol. 55 , 217, (1980)
  • Lin, H.L., et al. Cancer 85 , 1937-1942, (1999) 摘要
  • Schumacher, M.A., et al. Science 294 , 2158, (2001) 摘要
  • Beil. 27 ,II,567

安全信息

WGK Germany2
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
RTECSDR9866400
Signal word Warning
GHS Symbol
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
  • S36 Wear suitable protective clothing 穿戴适当的防护服;
  • 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
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R20/21/22 Harmful by inhalation, in contact with skin and if swallowed 吸入、皮肤接触和不慎吞咽有害
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
Packing GroupIII
Hazard Class6.1(b)
UN Number 1544
Hazard Codes Xn
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 37 mg/kg
TOXIC EFFECTS :
   Behavioral - convulsions or effect on seizure threshold
   Behavioral - excitement
   Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
   JPETAB Journal of Pharmacology and Experimental Therapeutics.  (Williams &
   Wilkins Co., 428 E. Preston St., Baltimore, MD 21202)  V.1-    1909/10-
   Volume(issue)/page/year: 104,253,1952

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 60 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   ZYZAEU Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. (China
   International Book Trading Corp., POB 2820, Beijing, Peop. China) V.24-
   1989-  Volume(issue)/page/year: 25,335,1990

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >29586 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Nutritional and Gross Metabolic - body temperature decrease
REFERENCE :
   KSRNAM Kiso to Rinsho.  Clinical Report.  (Yubunsha Co., Ltd., 1-5, Kanda
   Suda-Cho,

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >15 gm/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Nutritional and Gross Metabolic - body temperature decrease
REFERENCE :
   KSRNAM Kiso to Rinsho.  Clinical Report.  (Yubunsha Co., Ltd., 1-5, Kanda
   Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan)  V.1-    1960-
   Volume(issue)/page/year: 8,654,1974

TYPE OF TEST            : Gene conversion and mitotic recombination
TEST SYSTEM             : Yeast - Saccharomyces cerevisiae
DOSE/DURATION           : 25 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 286,243,1993

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Mammal - species unspecified Lymphocyte
DOSE/DURATION           : 22 umol/L
REFERENCE :
   IJBBBQ Indian Journal of Biochemistry and Biophysics.  (Publications &
   Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.8- 
     1971-  Volume(issue)/page/year: 18,245,1981

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Yeast - Saccharomyces cerevisiae
DOSE/DURATION           : 20 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 286,243,1993

其他信息

  • TCI Shanghai:氯化黄连素水合物 Berberi
  • 方法一:以黄樟油素为原料,在减压下异构化得异黄樟油素,经氧化生成胡椒醛。胡椒醛与硝基甲烷缩合得β-硝基-3,4-二氧亚甲基苯乙烯,进一步还原得胡椒乙胺[1484-85-1]:胡椒乙胺与邻藜芦醛缩合,再经催化氢化、成盐、环合,碱化得小檗碱。继续用盐酸成盐即得黄连素。1.缩合、催化氢化、成盐将无水乙醇与邻藜芦醛混合,在搅拌下再加胡椒乙胺,稍加热使全部溶解。搅拌10min以上使缩合反应完全。另将镍催化剂与无水乙醇混和后与缩合物一起投入高压釜。先通氮置换空气,再通入氢气,控制压力接近4MPa、温度80-90℃,将氢化反应进行到不再吸氢,并继续保温、保压通氢1h为止。冷至30℃,降压至2MPa,静置,使镍催化剂沉降,再利用高压釜余压将反应液压出。压滤除去催化剂(浸入乙醇,供下批套用),滤液在搅拌下于50℃用盐酸乙醇酸化至pH3-4,冷却至5℃,保持4h使结晶。过滤,用少量乙醇洗涤,干燥即得N-2,3-二甲氧苄基胡椒乙胺盐酸盐。收率84%。2.环合、碱化、成盐依次将冰醋酸、乙酐、硫酸铜及氯化钠投入反应锅中,搅拌升温至65-70℃,缓缓加入乙二醛,升温至回流20min,冷却至90℃,加N-2,3-二甲氧苄基胡椒乙胺盐酸盐,升温至112-114℃反应4h。减压回收乙酸至投料量的70-80%后,加水搅匀,过滤。滤饼用热水洗涤,滤干,即得小檗三盐酸盐粗品。粗品先用石灰乳碱化得pH8-8.5,过滤得到的小檗碱氢氧化物滤液和洗液,以稀盐酸调pH1-2,过滤,滤饼溶于热水,加活性炭脱色,过滤,用稀盐酸调pH1-2,冷却,过滤,水洗,干燥,即得黄连素。小檗碱存在于小檗科等四个科十个属的许多植物中,用提取法生产小檗碱的工艺过程是:取三颗针或十根地下根洗静,切成薄片,晒干,粉碎,加0.5%硫酸溶液加热浸泡3-4次,每次24h。第3、4次浸出液套用浸泡下一批生药。第1、2次浸出液过滤,滤液加氯化钠饱和,放置,把结晶分离出来即为粗品。粗品用酸碱法精制得成品。每百公斤生药可得成品0.5kg。
  • 可燃性危险特性:燃烧产生有毒氮氧化物烟雾;
  • 上游原料:硝基甲烷 --> 乙二醛 --> 胡椒醛 --> 黄樟素 --> 2,3-二甲氧基苯甲醛 --> 异黄樟素 --> 盐酸小檗碱
  • Sigma Aldrich:141433-60-5(sigmaaldrich)
  • 毒性分级:高毒
  • 用途二:黄连素为抗菌药物,是《国家基本药物目录》,选列的品种,该品对溶血性链球菌,金黄色葡萄球菌,淋球菌和弗氏、志贺氏痢疾杆菌等均有抗菌作用,并有增强白血球吞噬作用,
  • F:3-10
  • Alfa Aesar:<17% Berberine chloride hydrate, 97%, water <17%(141433-60-5)" href="http://www.alfa.com/zh/GP100w.pgm?DSSTK=L03807&CAS;=141433-60-5">氯化黄连素,97%,水<17% Berberine chloride hydrate, 97%, water <17%(141433-60-5)
  • 储运特性:低温通风低干燥; 因需求限量存储, 以防过量, 皮肤吸附中毒
  • 盐酸小檗碱价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/04/16 B0450 氯化黄连素水合物 Berberine Chloride Hydrate 25G 481元 2010/05/25 L03807 氯化黄连素,97%, 水 <17% Berberine chloride hydrate, 97%, water <17% 5g 246元 2010/05/25 L03807 氯化黄连素,97%, 水 <17% Berberine chloride hydrate, 97%, water <17% 25g 825元
  • 急性毒性:口服-小鼠 LD50: 329 毫克/公斤; 皮下-小鼠 LD50: 18 毫克/公斤
  • EPA化学物质信息:Benzo[g]-1,3-benzodioxolo[ 5,6-a]quinolizinium, 5,6-dihydro-9,10-dimethoxy-, chloride(633-65-8)

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