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191140

7-Aminocephalosporanic acid

Name: 7-Aminocephalosporanic acid
Brand: ALDRICH

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

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Properties

Quality Segment

200

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

Description

General description

Chemical structure: β-lactam

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.

pictograms

GHS08

signalword

Danger

hcodes

H317,H334

pcodes

P261 - P272 - P280 - P284 - P302 + P352 - P333 + P313

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c