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6-APA

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6-Aminopenicillanic acid
6-Aminopenicillanic acid
Names
IUPAC name (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4- thia-1-azabicycloheptane-2- carboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.177 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1Key: NGHVIOIJCVXTGV-ALEPSDHESA-N
  • InChI=1/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1Key: NGHVIOIJCVXTGV-ALEPSDHEBW
SMILES
  • O=C(O)1N2C(=O)(N)2SC1(C)C
Properties
Chemical formula C8H12N2O3S
Molar mass 216.25 g/mol
Melting point 198 - 200 °C
Boiling point > 200 °C (decomposes)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

6-APA is the chemical compound (+)-6-aminopenicillanic acid.

Use

6-APA is the core of penicillins. It is obtained from the fermentation brew of the Penicillium mold and used as the main starting block for the preparation of numerous semisynthetic penicillins.

Manufacture

This useful compound is made as follows:

Weissenburger, H. W. O.; Van der Hoven, M. G.; Recl. Trav. Chim. Pays-Bas 1970, 89, 1081.

References

  1. F.P. Doyle, J.H.C. Nayler, G.N. Rolinson US Patent 2,941,995, filed July 22, 1958, granted June 21, 1960. Recovery of solid 6-aminopenicillanic acid.

External links

See also

Category: