6-Aminopenicillanic acid

Names

[ CAS No. ]:
551-16-6

[ Name ]:
6-Aminopenicillanic acid

[Synonym ]:
[2S-(2a,5a,6b)]-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid
EINECS 208-993-4
6-aps
6-AMINO PENICILLINIC ACID
6-Aminopenicillanic acid
penicin
6-Aminopenicillansure
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
aminopenicillanicacid
MFCD00005176
6-APA
6b-Aminopenicillanic Acid
(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Amoxicillin Impurity 1

Biological Activity

[Description]:

6-Aminopenicillanic acid (6-APA) is an important precursor for the synthesis of -lactam antibiotics. 6-Aminopenicillanic acid is the main product of Penicillin G (PenG) hydrolyzed by penicillin acylase (PA)[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Lucie Vobecká, et al. Optimization of Aqueous Two-Phase Systems for the Production of 6-aminopenicillanic Acid in Integrated Microfluidic Reactors-Separators. N Biotechnol. 2018 Dec 25;47:73-79.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
460.2±45.0 °C at 760 mmHg

[ Melting Point ]:
198-200 °C (dec.)(lit.)

[ Molecular Formula ]:
C₈H₁₂N₂O₃S

[ Molecular Weight ]:
216.258

[ Flash Point ]:
232.1±28.7 °C

[ Exact Mass ]:
216.056870

[ PSA ]:
108.93000

[ LogP ]:
-0.36

[ Vapour Pressure ]:
0.0±2.4 mmHg at 25°C

[ Index of Refraction ]:
1.656

[ Storage condition ]:
2~8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XH8225000

CHEMICAL NAME :: 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-

CAS REGISTRY NUMBER :: 551-16-6

LAST UPDATED :: 199701

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C8-H12-N2-O3-S

MOLECULAR WEIGHT :: 216.28

WISWESSER LINE NOTATION :: T45 ANV ESTJ CZ F1 F1 GVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: AD691-490 ** TUMORIGENIC DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2600 mg/kg/65W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - tumors at site of application

REFERENCE :: BJCAAI British Journal of Cancer. (Macmillan Press Ltd., Houndmills, Basingstoke, Hants. RG21 2XS, UK) V.1- 1947- Volume(issue)/page/year: 19,392,1965 *** REVIEWS *** TOXICOLOGY REVIEW 22HAAD "Microbial Toxins, 1970-72," Ajil, S.J., et al., eds., New York, Academic Press, Inc., 1970-72 Volume(issue)/page/year: 6,409,1971 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-RUSSIA:STEL 0.4 mg/m3;Skin JAN 1993

Safety Information

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R42/43

[ Safety Phrases ]:
S22-S36/37-S45-S37-S24

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
XH8225000

[ HS Code ]:
2941109300

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2941109300

[ Summary ]:
2941109300. VAT:17.0%. Tax rebate rate:13.0%. Supervision conditions:Q(report of inspection of soundness on import medicines). MFN tariff:4.0%. General tariff:20.0%

Articles

Enhanced production of 6-aminopenicillanic acid in aqueous methyl isobutyl ketone system with immobilized penicillin G acylase.

Prep Biochem Biotechnol. 40(1) , 38-45, (2010)

Enzymatic hydrolysis of penicillin G for production of 6-amino-penicillanic-acid (6-APA) was achieved by using penicillin G acylase as catalyst in an aqueous-methylisobutyl ketone (MIBK) system. The o...

Monitoring bioreactors using principal component analysis: production of penicillin G acylase as a case study.

Bioprocess Biosyst. Eng. 33(5) , 557-64, (2010)

The complexity of biological processes often makes impractical the development of detailed, structured phenomenological models of the cultivation of microorganisms in bioreactors. In this context, dat...

Synthesis and biological evaluation of penem inhibitors of bacterial signal peptidase.

Bioorg. Med. Chem. Lett. 19(14) , 3787-90, (2009)

We report the first synthesis of a 5S penem, known to bind bacterial type I signal peptidase, from the commercially available and inexpensive 6-aminopenicillanic acid. We report the first in vivo acti...