All Photos(2)

191140

Sigma-Aldrich

7-Aminocephalosporanic acid

98%

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

Quality Level

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

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

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

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

An improved method for preparation of cefpodoxime proxetil
Rodriguez JC, et al.
Il Farmaco (Societa Chimica Italiana : 1989), 58(5), 363-369 (2003)
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
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
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
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

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