6-Aminopenicillanic acid

Modify Date: 2024-01-02 11:47:56

6-Aminopenicillanic acid Structure
6-Aminopenicillanic acid structure
Common Name 6-Aminopenicillanic acid
CAS Number 551-16-6 Molecular Weight 216.258
Density 1.5±0.1 g/cm3 Boiling Point 460.2±45.0 °C at 760 mmHg
Molecular Formula C8H12N2O3S Melting Point 198-200 °C (dec.)(lit.)
MSDS USA Flash Point 232.1±28.7 °C

 Use of 6-Aminopenicillanic acid


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].

 Names

Name 6-aminopenicillanic acid
Synonym More Synonyms

 6-Aminopenicillanic acid 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
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

 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

 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%

 Articles27

More 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...

 Synonyms

[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
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