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Merck
CN

191140

7-Aminocephalosporanic acid

98%

Synonym(s):

7-ACA

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About This Item

Empirical Formula (Hill Notation):
C10H12N2O5S
CAS Number:
957-68-6
Molecular Weight:
272.28
UNSPSC Code:
12352106
NACRES:
NA.22
PubChem Substance ID:
24851470
EC Number:
213-485-0
Beilstein/REAXYS Number:
622637
MDL number:
MFCD00005177

Key Documents

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Product Name

7-Aminocephalosporanic acid, 98%

InChI key

HSHGZXNAXBPPDL-HZGVNTEJSA-N

InChI

1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)/t6-,9-/m1/s1

SMILES string

[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2N)C(O)=O

assay

98%

form

powder

optical activity

[α]19/D +90°, c = 0.5 in KH2PO4/trace NaOH

reaction suitability

reaction type: solution phase peptide synthesis

mp

>300 °C (lit.)

antibiotic activity spectrum

Gram-positive bacteria

application(s)

peptide synthesis

mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

Quality Level

200

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Application

7-Aminocephalosporanic acid (7-ACA) can be used as a starting material to synthesize:
  • Cefotaxime by acylation reaction with S-benzothiazol-2-yl(2-amino-4-thiazolyl)(methoxyimino)thioacetate (MAEM) in the presence of triethylamine.
  • Cefpodoxime proxetil, a third-generation antibiotic via cefotaxime intermediate.
  • Sodium 3′-substituted cephalosporanate sulfone derivatives as potential inhibitors of β-lactamase.

Potent inhibitor of bacterial (S. aureus) β-lactamase.

General description

Chemical structure: ß-lactam

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS4234
MKBZ8828V
MKBR1128V
MKBL2298V
MKBK3641V

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Denis L Atroshenko et al.
International journal of molecular sciences, 20(18) (2019-09-11)
d-amino acid oxidase (DAAO, EC 1.4.3.3) is used in many biotechnological processes. The main industrial application of DAAO is biocatalytic production of 7-aminocephalosporanic acid from cephalosporin C with a two enzymes system. DAAO from the yeast Trigonopsis variabilis (TvDAAO) shows
Synthesis and Preliminary Biological Evaluation of 3?-Substituted Cephem Sulfones as Potential β-Lactamase Inhibitors
De Angelis F, et al.
European Journal of Organic Chemistry, 2001(16), 3075-3081 (2001)
Zhanglin Lin et al.
Biotechnology and bioengineering, 117(10), 2923-2932 (2020-06-17)
Site-directed protein immobilization allows the homogeneous orientation of proteins with high retention of activity, which is advantageous for many applications. Here, we report a facile, specific, and efficient strategy based on the SpyTag-SpyCatcher chemistry. Two SpyTag-fused model proteins, that is
Cosmin Butnarasu et al.
International journal of pharmaceutics, 564, 136-144 (2019-04-17)
Mucin is a complex glycoprotein consisting of a wide variety of functional groups that can interact with exogenous agents. The binding to mucin plays a crucial role in drug pharmacokinetics especially in diseases, such as cystic fibrosis (CF), where mucin
An improved method for preparation of cefpodoxime proxetil
Rodriguez JC, et al.
Il Farmaco (Societa Chimica Italiana : 1989), 58(5), 363-369 (2003)
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