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7-Aminocephalosporanic acid

Synthetic cephalosporins important nucleus β-lactam antibiotics Chemical Properties Uses production method
7-Aminocephalosporanic acid
7-Aminocephalosporanic acid structure
CAS No.
957-68-6
Chemical Name:
7-Aminocephalosporanic acid
Synonyms
7-ACA;7-ACS;7-Amino;7-ACA Impurity;7-ACA fandachem;Aminocephalosporanic;Cefalotin Impurity C;Cefradine impurity A;7-Aminocephalosporan;Cefuroxim Impurity 25
CBNumber:
CB8344119
Molecular Formula:
C10H12N2O5S
Formula Weight:
272.28
MOL File:
957-68-6.mol

7-Aminocephalosporanic acid Properties

Melting point:
>300 °C (lit.)
Boiling point:
560.6±50.0 °C(Predicted)
alpha 
94 º (c=0.5, KH2PO4, PH 7)
Density 
1.4667 (rough estimate)
refractive index 
1.5650 (estimate)
storage temp. 
2-8°C
pka
2.59±0.50(Predicted)
form 
Crystalline Powder
color 
Off-white to beige
optical activity
[α]19/D +90°, c = 0.5 in KH2PO4/trace NaOH
Water Solubility 
409.6mg/L(22.99 ºC)
Merck 
14,434
BRN 
622638
Stability:
Hygroscopic
InChIKey
HSHGZXNAXBPPDL-HZGVNTEJSA-N
CAS DataBase Reference
957-68-6(CAS DataBase Reference)
FDA UNII
9XI67897RG
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS08
Signal word  Danger
Hazard statements  H315-H319-H317-H334
Precautionary statements  P280g-P304+P340-P342+P311a-P501a-P261-P280-P342+P311-P264-P272-P284-P302+P352+P333+P313+P363-P304+P340+P342+P311-P305+P351+P338+P337+P313-P501
Hazard Codes  Xn,Xi
Risk Statements  42/43-36/37/38-20/21/22
Safety Statements  22-36/37-24/25-36-26
WGK Germany  3
HS Code  29349960

7-Aminocephalosporanic acid price More Price(6)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 191140 7-Aminocephalosporanic acid 98% 957-68-6 5g $97.5 2021-03-22 Buy
TCI Chemical A1266 7-Aminocephalosporanic Acid >97.0%(HPLC)(T) 957-68-6 5g $29 2021-03-22 Buy
TCI Chemical A1266 7-Aminocephalosporanic Acid >97.0%(HPLC)(T) 957-68-6 25g $109 2021-03-22 Buy
Alfa Aesar A10530 7-Aminocephalosporanic acid, 98% (dry wt.), may cont. up to 2% water 957-68-6 1g $33.5 2021-03-22 Buy
Alfa Aesar A10530 7-Aminocephalosporanic acid, 98% (dry wt.), may cont. up to 2% water 957-68-6 5g $101 2021-03-22 Buy

7-Aminocephalosporanic acid Chemical Properties,Uses,Production

Synthetic cephalosporins important nucleus

7-aminocephalosporanic acid is abbreviated as 7-ACA, white or almost white crystalline powder, 7-ACA is an important nucleus in synthesis of cephalosporin antibiotics, in the nucleus 7 and 3 chemical transformation can be used to prepare many cephalosporins: cefazolin sodium , cefotaxime sodium, ceftriaxone sodium, cefoperazone sodium, sodium ceftazidime, cefuroxime sodium.
Cephalosporin antibiotics (Cephalosporins) are a cluster of broad-spectrum semisynthetic antibiotics, they all contain the nucleus of 7-aminocephalosporanic acid (7-ACA) , with different groups in the 3 and 7 carbon atoms, forming various cephalosporins with different antibacterial activity and pharmacokinetic characteristics. Cephalosporin antibiotics have broad antibacterial spectrum,strong antibacterial effect, and fewer allergic reactions, and only part of the cross allergic with penicillin and they have varying degrees of stability on the β-lactamase . Cephalosporins have fast development, and many families, they are divided into four generation cephalosporins according to the anti-microbial dynamic "generations" .
They are the same as penicillin, cephalosporins contain β lactam ring , which is necessary to achieve antibacterial efficacy. But penicillins are 6-amino penicillin acid (6-aminopenicillanic acid, 6-APA) derivatives, and cephalosporins nucleus is 7-aminocephalosporanic acid (7-aminocephalosporamic acid, 7-ACA), the latter is from cephalosporin C, it is a fermentation product of Cephalosporium acremonium.
7-aminocephalosporanic acid has a dihydro-thiazine ring (A) and aβ-lactam ring (B), it has a resistant effect on the class of staphylococcus aureus penicillinase. Modifying this nucleus with different side chains can form the entire series of cephalosporin antibiotics. Modifying β-lactam bit 7 (R1), can make antimicrobial efficacy and stability within the β-lactamase change. At 3 bit on-dihydro-thiazine ring substitution (R2), the influence of effect on drug metabolism and pharmacokinetic properties is more staggering than that of antibacterial effect.
Cephamycins are associated with cephalosporin C in chemical structure, the main difference is that they have a 7-α-methoxy group (R3), so that the stability to certain β-lactamase is improved . Cephalosporin is a derivative cephalosporin C which is produced by Streptomyces . Cefotetan is an semi-synthetic derivative of organic mycin G , it is a product of Streptomyces organonensis. Cefmetazole is a semi-synthetic product of 7-aminocephalosporanic acid.

Figure 1 the chemical structure of the 7-aminocephalosporanic acid

β-lactam antibiotics

6-aminopenicillanic acid (6-APA), 7-aminocephalosporanic acid (7-ACA), 3-ammonia Ji Nuoka adriamycin (3-ANA), and 3-amino-acid mono-(3-AMA)are important raw materials of the semi-synthetic β-lactam. In the β-lactam antibiotics mean antibiotics that molecules contain β lactam ring (β-lact-am), including penicillins, cephalosporins, monocyclic beta-lactam antibiotics and the like. Such antibiotics have antibacterial action, the β-lactam portion is similar to D-alanyl-D-alanine terminus of the bacterial cell wall peptidoglycan,they can be combined with endopeptidase activity center, so that the GGT sticky peptidase-catalyzed cross-linking reaction can not be completed, thereby cell wall synthesis is inhibited . As these antibiotics act not only on the cell walls of bacteria, but also interfere with cell wall formation which occurs in the final stages of biosynthesis, so they show unique selectivity on bacteria , there is almost no damage to animal cells which do not have the cell wall ,they are a class of relatively good chemotherapeutic drugs. β-lactam antibiotics are susceptible to β-lactamase destruction which leads to deactivation of them. Some β lactams are β-lactamase (β-lactamase) inhibitors, in combination with the β-lactam antibiotics, the antibiotics can be protected or less destroyed by them , they are important adjuncts to chemotherapy.
The above information is edited by the chemicalbook of Tian Ye.

Chemical Properties

Crystals.

Uses

Pharmaceutical intermediates. It is the starting material of many semi-synthetic cephalosporin. A variety of semi-synthetic cephalosporin industrial production is through fermentation to obtain cephalosporin C. Then obtain nucleus 7-ACA through chemical cleavage , and then the preparation is fininshed in chemically modified way .

production method

Starting from the basic raw material of semi-synthetic cephalosporin-cephalosporin C, after esterification with trimethylchlorosilane , and then by phosphorus pentachloride chloride, and Butanol etherifying, and the production is obtained finally through hydrolysis. Yield from cephalosporin C sodium to 7-ACA is about 50%.

Chemical Properties

Off-white to beige crystalline powder

Uses

It is the starting material for semi-synthetic cephalosporins. Obtained by mild acid hydrolysis of cephalosporin C.

Uses

Antibacterial;Bacterial transpeptidase inhibitor

Definition

ChEBI: The alpha,beta-unsaturated monocarboxylic acid that is the active nucleus for the synthesis of cephalosporins and intermediates.

7-Aminocephalosporanic acid Preparation Products And Raw materials

Raw materials

Preparation Products


7-Aminocephalosporanic acid Suppliers

Global( 346)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Hubei Jusheng Technology Co.,Ltd.
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027-59599243 linda@hubeijusheng.com CHINA 28229 58
Guangzhou PI PI Biotech Inc
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020-81716319 sales@pipitech.com;87478684@qq.com China 3245 55
Henan DaKen Chemical CO.,LTD.
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Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Shanghai Time Chemicals CO., Ltd.
+8618017249410 +86-021-57951555
+86-021-57951555 jack.li@time-chemicals.com CHINA 1365 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8910 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070
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ATK CHEMICAL COMPANY LIMITED
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career henan chemical co
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Jinan Finer Chemical Co., Ltd
+8615508631887 +86-531-88989536
+86-531-88989539 sales@finerchem.com CHINA 1716 58

View Lastest Price from 7-Aminocephalosporanic acid manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-12-08 7-Aminocephalosporanic acid
957-68-6
US $0.00 / KG 1KG 99% 100mt Jinan Finer Chemical Co., Ltd
2021-12-01 7-Aca 7-Aminocephalosporanic Acid
957-68-6
US $8.00 / Kg/Bag 10g 99% 10000kg Hebei Crovell Biotech Co Ltd
2021-11-15 7-Aminocephalosporan
957-68-6
US $34.10 / KG 1KG 99% 500ton/Month Hebei Yirun Sega Biological Technology Co. Ltd

7-Aminocephalosporanic acid Spectrum


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