6-Aminopenicillanic acid 6-氨基青霉烷酸

CAS 551-16-6 MFCD00005176

化学结构图

551-16-6
SMILES: CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O

化学属性

Mol. FormulaC8H12N2O3S
Mol. Weight216
Melting Point198-200
TSCAYes
Density1.52
Appearance 白色或微黄色结晶粉末。熔点208-209℃（分解）。微溶于水，不溶于乙酸丁酯、乙醇或丙酮。遇碱分解，对酸较稳定。

别名和识别编码

Chemical Name6-Aminopenicillanic acid
CAS Number551-16-6
Alfabeta NameAMINOPENICILLANICACID 6-
MDL NumberMFCD00005176
Synonym 6-Aps (2S,5R,6R)-6-AMINO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO-[3.2.0]HEPTANE-2-CARBOXYLIC ACID 6-Apa 3-二甲基-7-氧代-4-硫杂-1-氮杂二环[3.2.0]庚烷-2-羧酸-6-氨基-3 无侧链青霉素 6-amino penicillanic acid(6-APA) ######## 6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-ca phenacyl6-aminopenicillinate 6-氨基头孢菌素 Penicin (+)-6-氨基青霉烷酸 6-氨基青霉素酸 Phenacyl 6-aminopenicillinate Penin 6-Aminopenicillanic acid (2S,5R,6R)-6-氨基-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸 6-氨基青霉烷酸 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-amino-3,3-dimethyl-7-oxo 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, [2S-(2alpha,5alpha,6beta)]- (2S,5R,6R)-6-氨基-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸 6-APA 7-AMINO-3,3-DIMETHYL-6-OXO-2-THIA-5-AZABICYCLO[3.2.0]HEPTANE-4-CARBOXYLIC ACID (+)-6-AMINOPENICILLANIC ACID 6-AMINO-2,2-DIMETHYL-5-OXOPERHYDROAZETO[2,1-B][1,3]THIAZOLE-3-CARBOXYLIC ACID 6-APA aminopenicillanicacid 6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-APA 5alpha,6beta)]-[2s-(2alpha 6-氨基-3,3-二甲基-7-氧代-4-硫杂-1-氮杂二环[3.2.0]庚烷-2-羧酸- 6-AMINOPENICILLANIC ACID penin 6-aps 6-AMINO PENICILLINIC ACID 盐酸文拉法新 penicin 6-amino-3,3-dimethyl-7-oxo-,[2S-(2.alpha.,5.alpha.,6.beta.)]-4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid 6-氨基青霉酸
PubChem Substance ID87562327
EC Number208-993-4
Beilstein Registry Number15080
Reaxys-RN15080
Merck Number458
Chemical Name Translation6-氨基青霉烷酸
Wiswesser Line NotationT45 ANV ESTJ CZ F1 F1 GVQ
LabNetwork Molecule IDLN00171432
InChIInChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1
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分类

  • {SNA} A - K,
  • {SNA} Analytical Standards, Analytical/Chromatography, Chromatography, EP Standards, EP Standards E - F, Pharmaceutical Standards, Pharmacopeia Standards
  • {SNA} Analytical Standards, EP Standards,
  • {SNA} A - K, Antibacterial, Antibiotics A to Z, Antibiotics A-F, Asymmetric Synthesis, Chemical Structure Class, Chemical Synthesis, Chiral Building Blocks, Heterocyclic Building Blocks, Interferes with Cell Wall Synthesis, Mechanism of Action, Other Heterocyclic Building Blocks, Penicillins and Cephalosporins (beta-Lactams), Spectrum of Activity, 抗生素, 生化试剂

产品应用

  • 制备半合成青霉素的原料。

相关文献及参考

  • Zel'tser, I.Z. et al.: Gig. Truda Prof. Zabol., 5, 59 (1983); Hamilton-Miller, J.M.T.: Int. J. Antimicrob. Agents, 31, 189 (2008); Novikova, N.D. et al.: Mikol. Fitopatol., 7, 101 (1973);
  • Merck:14,458 Beilstein: 27,IV,5858
  • Merck:14,458

安全信息

Warnings IRRITANT
GHS Symbol
WGK Germany2
Hazard Codes Xn
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H317 May cause an allergic skin reaction 可能导致皮肤过敏
  • H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled 吸入可能导致过敏或哮喘症状或呼吸困难
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Faceshields, Gloves
RTECSXH8225000
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。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P272 Contaminated work clothing should not be allowed out of the workplace. 污染的工作服不得带出工作场所。
  • 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。
  • P284 Wear respiratory protection.? 佩戴呼吸保护装置。
  • P285 In case of inadequate ventilation wear respiratory protection. 在通风不足的情况下，戴呼吸防护。
  • P302+P350
  • P302+P352+P333+P313+P362+P364
  • P304+P340+P342+P311
  • P304+P341
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P337+P313
  • P342+P311
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Danger
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘；
  • S24 Avoid contact with skin 避免皮肤接触；
  • 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；
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
  • 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；
  • S37 Wear suitable gloves 戴适当手套；
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
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
  • R42/43
Storage condition 储存温度：2-8℃ 2-8°C 储存温度2-8°C 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 2600 mg/kg/65W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Tumorigenic - tumors at site of application
REFERENCE :
   BJCAAI British Journal of Cancer.  (Macmillan Press Ltd., Houndmills,
   Basingstoke, Hants. RG21 2XS, UK)  V.1-    1947-  Volume(issue)/page/year:
   19,392,1965

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: AD691-490

其他信息

  • 微溶于水，不溶于乙酸丁酯、乙醇或丙酮。遇碱分解，对酸较稳定。
  • 用途一:用作医药中间体
  • 用途二:制备半合成青霉素的原料。
  • 比旋光度:276.3 ° (c=1.2, 0.1N HCl 22 °C)
  • 上游原料:碳酸氢铵 --> 氨苄青霉素 --> 青霉素钾 --> 双二甲胺基乙基醚 --> 亚胺 --> 氨苄青霉素
  • TCI Shanghai:6-氨基青霉烷酸 6-Aminopenicillanic Acid,>;98.0%(T)(551-16-6)
  • MOL 文件:551-16-6.mol
  • MSDS 信息:6-Aminopenicillanic acid(551-16-6).msds
  • 6-氨基青霉烷酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 A0800 6-氨基青霉烷酸 6-Aminopenicillanic Acid 25G 410元 2014/06/02 A0800 6-氨基青霉烷酸 6-Aminopenicillanic Acid 5G 110元 2010/06/21 104250100 6-氨基青霉烷酸 6-Aminopenicillanic acid 96% 10 GR 424元
  • Sigma Aldrich:551-16-6(sigmaaldrich)
  • 图谱信息:6-氨基青霉烷酸(551-16-6)红外图谱(IR1) 6-氨基青霉烷酸(551-16-6)质谱(MS) 6-氨基青霉烷酸(551-16-6)红外图谱(IR2)
  • F:10
  • Acros Organics:6-氨基青霉烷酸 6-Aminopenicillanic acid, 96%(551-16-6)
  • Alfa Aesar:6-氨基青霉烷酸,98% 6-Aminopenicillanic acid, 98%(551-16-6)
  • 方法一:有固相酶法和化学裂解法。化学裂解法以青霉素G钾盐为原料，经缩合，氯化、醚化得到双亚胺醚：然后，将双亚胺醚加入0℃的蒸馏水中，降温至-13±1℃水解20min，加氨水（中途加晶种），加完后，控制温度13-15℃，加碳酸氢铵调pH至4.1保温20min，过滤，丙酮洗涤，干燥，得6-APA。
  • 海关编码:29349990
  • 下游产品:亚胺培南(一水物) --> 青霉素 --> 哌拉西林 --> 苯唑青霉素钠 --> 羧苄西林

系列性分类

  1. Life Science 生命科学
  2. Antibiotics 抗生素
  3. Antibiotics A to Z - Antibiotics
  4. Antibiotics A-F - Antibiotics A to Z
  1. Life Science 生命科学
  2. Antibiotics 抗生素
  3. Mechanism of Action - Antibiotics
  4. Interferes with Cell Wall Synthesis - Mechanism of Action
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Isoquinolines 异喹啉
  1. Chemical Synthesis 化学合成
  2. Asymmetric Synthesis 不对称合成
  3. Chiral Building Blocks 手性分子砌块
  4. Heterocyclic Building Blocks - Chiral Building Blocks
  5. Others - Heterocyclic Building Blocks
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Antibiotics
  4. Chemical Structure Class
  5. Nucleosides
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Antibiotics
  4. Mechanism of Action
  5. Interferes with Cell Membrane Permeability (Ionophores)
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Antibiotics
  4. Spectrum of Activity
  5. Antibacterial

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