Synthetic cephalosporins important nucleus β-lactam antibiotics Chemical Properties Uses production method
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7-Aminocephalosporanic acid

Synthetic cephalosporins important nucleus β-lactam antibiotics Chemical Properties Uses production method
Product Name
7-Aminocephalosporanic acid
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;Cefuroxim Impurity 25;Cefuroxime Impurity 25
CBNumber
CB8344119
Molecular Formula
C10H12N2O5S
Formula Weight
272.28
MOL File
957-68-6.mol
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7-Aminocephalosporanic acid Property

Melting point:
>300 °C (lit.)
alpha 
94 º (c=0.5, KH2PO4, PH 7)
Boiling point:
560.6±50.0 °C(Predicted)
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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

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

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7-Aminocephalosporanic acid Suppliers

XiaoGan ShenYuan ChemPharm co,ltd
Tel
0712-2580635- ;0712-2580635
Email
1791901229@qq.com;1791901229@qq.com;
Country
China
ProdList
8945
Advantage
52
Nanjing XiLang Chemical Products Co., Ltd.
Tel
025-5276156
Email
chemxilang@163.com
Country
China
ProdList
3972
Advantage
58
Anqing Hua Qi Chemical Technology Co., Ltd.
Tel
13721102221
Fax
0551-65651325
Country
China
ProdList
34
Advantage
58
Suizhou HongQi Chemical Corporation Limited
Tel
0722-3257376- ;0722-3257386- ;0722-3257313-
Fax
0722-3257381
Email
774811011@qq.com;2582618620@qq.com;2582618620@qq.com
Country
China
ProdList
66
Advantage
55
Suizhou Jiake Biological Engineering Co., Ltd.
Tel
0722-3632789- ;0722-3632989-
Fax
0722-3255139
Email
2549463910@qq.com;2286801987@qq.com
Country
China
ProdList
118
Advantage
58
Taizhou Huaxi Technology Co. LTD
Tel
0576-89164227- ;
Fax
0576-89164227
Email
18323010@qq.com;97621963@qq.com
Country
China
ProdList
32
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
21-61259100-
Fax
86-21-61259102
Email
sh@meryer.com
Country
China
ProdList
40264
Advantage
62
INTATRADE GmbH
Tel
+49 3493/605464
Fax
+49 3493/605470
Email
sales@intatrade.de
Country
Germany
ProdList
3579
Advantage
66
future industrial shanghai co., ltd
Tel
400-0066-400;021-60496031
Fax
021-55660885
Email
sales@jonln.com;sales@jonln.com
Country
China
ProdList
2000
Advantage
65
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View Lastest Price from 7-Aminocephalosporanic acid manufacturers

Wuhan wingroup Pharmaceutical Co., Ltd
Product
7-Aminocephalosporanic acid 957-68-6
Price
US $8.00/KG
Min. Order
100g
Purity
99%
Supply Ability
1000MT/Month
Release date
2021-07-13
Jinan Finer Chemical Co., Ltd
Product
7-Aminocephalosporanic acid 957-68-6
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100mt
Release date
2019-07-03
Hebei Crovell Biotech Co Ltd
Product
7-Aca 7-Aminocephalosporanic Acid 957-68-6
Price
US $8.00/Kg/Bag
Min. Order
10g
Purity
99%
Supply Ability
10000kg
Release date
2021-06-18

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