191140

Sigma-Aldrich

7-Aminocephalosporanic acid

98%

Synonym(s):
7-ACA
Empirical Formula (Hill Notation):
C10H12N2O5S
CAS Number:
Molecular Weight:
272.28
Beilstein/REAXYS Number:
622637
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

optical activity

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

reaction suitability

reaction type: solution phase peptide synthesis

application(s)

peptide synthesis: suitable

mp

>300 °C (lit.)

Mode of action

cell wall synthesis | interferes

antibiotic activity spectrum

Gram-positive bacteria

storage temp.

2-8°C

SMILES string

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

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

InChI key

HSHGZXNAXBPPDL-HZGVNTEJSA-N

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General description

Chemical structure: ß-lactam

Application

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

Packaging

5 g in glass bottle

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

hazcat

Resp. Sens. 1 - Skin Sens. 1

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
Dongxue Hu et al.
Bioresource technology, 304, 123014-123014 (2020-02-24)
In this study, a lab-scale multiple draft tubes airlift loop membrane bioreactor (Mt-ALMBR) was used for treating acidic 7-amino cephalosporanic acid (7-ACA) wastewater under different pHs (3.54-6.20) and hydraulic retention time (HRT) (48 h, 36 h, 24 h and 16 h). During about 200 days...
Irene Martínez-Martínez et al.
Analytical biochemistry, 369(2), 210-217 (2007-07-27)
A bromothymol blue-based colorimetric assay has been devised to screen for acetyl xylan esterase or cephalosporin C (CPC) deacetylase activities using 7-amino cephalosporanic acid (7-ACA), CPC, or acetylated xylan as substrate. These enzymes are not screened with their natural substrates...
Kristóf Kóczián et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 32(1), 1-7 (2007-06-26)
Acid-base chemistry of 6-aminopenicillanic acid (6-APA) and 7-aminocephalosporanic acid (7-ACA), the fundamental units of the two classical antibiotic families is characterised at the macroscopic and microscopic levels. (1)H NMR-pH and pH-potentiometric titrations were combined to monitor the previously unreported extent...
Julia Märk et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 76(2), 320-327 (2010-07-06)
NIR spectroscopy was applied to develop a fast and reliable quality control system for a pharmaceutical substance to support information obtained through PAT surveillance of its manufacturing process. After calculating different quantitative calibrations of the substance's key quality parameters, a...

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