6-APA

6-Aminopenicillanic acid

Names
IUPAC name (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4- thia-1-azabicyclo[3.2.0]heptane-2- carboxylic acid
Identifiers
CAS Number	551-16-6 N
3D model (JSmol)	Interactive image
ChemSpider	10611
ECHA InfoCard	100.008.177
PubChem CID	11082
CompTox Dashboard (EPA)	DTXSID7046097
InChI 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/s1 Key: NGHVIOIJCVXTGV-ALEPSDHEBW
SMILES O=C(O)[C@@H]1N2C(=O)[C@@H](N)[C@H]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 [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

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.

External links

• US 2,941,995 on espacenet

See also

• 7-ACA