7-Aminocephalosporanic acid

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7-Aminocephalosporanic acid

Product Name: 7-Aminocephalosporanic acid
CAS No.: 957-68-6
Chemical Name: 7-Aminocephalosporanic acid
Synonyms: 7-ACA;(6R,7R)-3-(acetoxyMethyl)-7-aMino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;7-ACS;7-Amino;7-ACA Impurity;D-7-ACA Impurity 4;Aminocephalosporanic;Cefalotin Impurity C;Cefradine impurity A;7-Aminocephalosporan
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)
vapor pressure: 0Pa at 20℃
refractive index: 1.5650 (estimate)
storage temp.: 2-8°C
solubility: DMSO (Very Slightly, Heated)
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
LogP: -3.4 at 20℃
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

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

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

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

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

P284Wear respiratory protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 191140
Product name: 7-Aminocephalosporanic acid
Purity: 98%
Packaging: 5g
Price: $37.56
Updated: 2024/03/01

TCI Chemical

Product number: A1266
Product name: 7-Aminocephalosporanic Acid
Purity: >97.0%(HPLC)(T)
Packaging: 5g
Price: $36
Updated: 2024/03/01

TCI Chemical

Product number: A1266
Product name: 7-Aminocephalosporanic Acid
Purity: >97.0%(HPLC)(T)
Packaging: 25g
Price: $132
Updated: 2024/03/01

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: 2021/12/16

Alfa Aesar

Product number: A10530
Product name: 7-Aminocephalosporanic acid, 98% (dry wt.), may cont. up to 2% water
Packaging: 5g
Price: $101
Updated: 2021/12/16

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7-Aminocephalosporanic acid Chemical Properties,Usage,Production

Description

The abbreviation for 7-aminocephalosporanic acid is 7-ACA. It is a white or almost white crystalline powder and serves as a crucial nucleus in the production of cephalosporin antibiotics. By utilizing chemical transformations at positions 7 and 3 of the nucleus, numerous cephalosporins can be synthesized, including cefazolin sodium, cefotaxime sodium, ceftriaxone sodium, cefoperazone sodium, sodium ceftazidime, and 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

Chemical Properties

Off-white to beige crystalline powder

Uses

7-Aminocephalosporanic Acid (Cefoperazone EP Impurity E) is the starting material for semi-synthetic cephalosporins. Obtained by mild acid hydrolysis of cephalosporin C.

Uses

Potent antibacterial that inhibits bacterial transpeptidase and β-lactamase activity in Staphylococcus aureus.

Definition

ChEBI: 7-Aminocephalosporanic acid is the alpha,beta-unsaturated monocarboxylic acid that is the active nucleus for the synthesis of cephalosporins and intermediates. It is functionally related to a cephalosporanic acid. It is a tautomer of a 7beta-aminocephalosporanic acid zwitterion.

Preparation

The synthesis of 7-Aminocephalosporanic acid involves esterification of semi-synthetic cephalosporin-cephalosporin C with trimethylchlorosilane, followed by phosphorus pentachloride chloride and butanol etherifying. The final product is obtained through hydrolysis. The yield from cephalosporin C sodium to 7-ACA is approximately 50%.
DOI: 10.3390/jof8050450

General Description

The chemical class of 7-aminocephalosporanic acid is Beta-Lactams. This class includes several antibiotic families, such as penicillins, cephalosporins, carbapenems, and monobactams. The Beta-lactam ring is part of the core structure of these families, which is why they are also referred to as Beta-lactam antibiotics.

Flammability and Explosibility

Not classified

7-Aminocephalosporanic acid Preparation Products And Raw materials

Raw materials

Chlorotrimethylsilane 7-(5-amino-5-carboxyvaleramido)cephalosporanic acid Phosphorus pentachloride

Preparation Products

7-(ALPHA-BROMOACETAMIDO)CEPHALOSPORANIC ACID Cefteram pivoxil Cefotaxime Cephalothin sodium

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View Lastest Price from 7-Aminocephalosporanic acid manufacturers

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

Ouhuang Engineering Materials (Hubei) Co., Ltd

Product: 7-Aminocephalosporanic acid 957-68-6
Price: US $15.00/kg
Min. Order: 1kg
Purity: 99.912%
Supply Ability: 10ton
Release date: 2024-04-23

Hangzhou ICH Biofarm Co., Ltd

Product: 7-Aminocephalosporanic Acid 957-68-6
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 99.0%
Supply Ability: 20 tons
Release date: 2023-06-27

957-68-6, 7-Aminocephalosporanic acidRelated Search:

Folic acid DL-ALPHA-AMINOPIMELIC ACID Ethyl 2-(Chlorosulfonyl)acetate Acetaminophen Isopropyl 3-aminocrotonate 6-Aminocaproic acid N-Acetylsulfanilyl chloride Cephalothin ALTRENOGEST 2-AMINODIETHYLMALONATE Glycine Hydroxymethyl-7-Aminocephalosporanic acid 6-isoquinolinecarboxylic acid Cefazolin IMpurity C Cefazolin SodiuM iMpurity G 7-Amino-3-[(5-methyl-1,3,4-thiadiazol-2-ylthio)methyl]-3-cephem-4-carboxylic Acid 2-Mercapto-5-methyl-1,3,4-thiadiazole (6R-trans)-3-(acetoxymethyl)-8-oxo-7-(1H-tetrazol-1-ylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Cefazolin Sodium EP Impurity H (7-Aminocephalosporanic Acid)

Cephalothin Impurity C(EP)（7-ACA）

Aminocephalosporanic

Cefazolin EP Impurity H

7-ACA Impurity

Ceftriaxone Impurity 18

(6R,7R)-3-(acetyloxymethyl)-7-ammonio-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

7-AMinocephalosporanic acid 98%

7-Aminocephalosporanic acid, Antibiotic for Culture Media Use Only

Cephalosporin Intermediate: 7-Aminocephalosporanic Acid

Cefazolin Sodium Impurity H

(6r,7s)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

7-AMINOCEPHALOSPORANIC ACID

7-ACA

3-acetoxymethylen-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

7-Aminocephalsporanic acid

7-Aminocephalosporanicacid,99%

3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

7-Aminocephalosporanic acid, 95-102%

(6R,TRANS)-3-[(ACETYLOXY)METHYL]-7-AMINO-8-OXO-5-THIA-1-AZABICYCLO[4.2.0]-OCT-2-CARBOXYLID ACID

7-Amino

7-Amino-3-Methoxycephalosporanic Acid（7-Amca）

5-Thia-1-azabicyclo4.2.0oct-2-ene-2-carboxylic acid, 3-(acetyloxy)methyl-7-amino-8-oxo-, (6R,7R)-

7-AMINO CEPHALOSPORIC ACID

7-AMINOCEPHALOSPORANIC ACID (7-ACA)

7-ACA (7-AMINOCEPHALOSPORANIC ACID)

7-AMINOCEPHALOSPORIC ACID (7-ACA)

7beta-aminocephalosporanic acid

Cefalotin Impurity C

Cefoperazone EP Impurity E

Cefradine impurity A

7-Aminocephalosporanic acid, 97%, a potent β-lactamase inhibitor

Cefazolin Impurity 1(Cefazolin EP Impurity H)

Cefoperazone Impurity 5(Cefoperazone EP Impurity E)

Ceftazidime Impurity 25

Cefuroxime Impurity 25

7-AMinocephalosporanic acid, 95-102% 1GR

7-AMinocephalosporanic acid, 95-102% 5GR

7-Aminocephalosporanic acid ,97%

7-Amino-3-acetoxymethyl-3-cephem-4-carboxylic acid

7-Amino-3-acetoxymethyl-D3-cephem-4-carboxylic acid

7b-Amino-3-acetoxymethylcephemcarboxylic acid

(6R,7R)-7-Amino-3-[(acetyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(7R)-3-Acetyloxymethyl-7-aminocepham-3-ene-4-carboxylic acid

3-(Acetoxymethyl)-7β-aminocepham-3-ene-4-carboxylic acid

7-ACS

7-Amino-3-(acetoxymethyl)cepham-3-ene-4-carboxylic acid

7-Amino-3-acetoxymethylcepham-3-ene-4-carboxylic acid

7-Aminocephalosporanic acid, 98% (dry wt.), may cont. up to 2% water

(6R,7R)-3-[(Acetyloxy)Methyl]-7-aMino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

(7R)-7-AMinocephalosporanic Acid

3-(AcetoxyMethyl)-7-aMinocepheM -4-carboxylic Acid

(6R,7R)-3-(acetoxyMethyl)-7-aMino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6r,7s)-3-(acetyloxyMethyl)-7-aMino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 7-ACA 7-AMINOCEPHALOSPORANIC ACID 3-acetoxyMethylen-7-aMino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 7-AMinocephalsporanic acid

pharMaceautical interMediate

7-Aminocephalosporanic Acid &gt

(6R,7R)-3-[(Acetyloxy)methyl]-7-ami

Ceftriaxone IP Impurity E