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6-Aminopenicillanic acid

6-Aminopenicillanic acid Structure
CAS No.
551-16-6
Chemical Name:
6-Aminopenicillanic acid
Synonyms
6-APA;6-amino penicillanic acid(6-APA);6-Amino;Flucloxacillin EP Impurity C;AMoxicillin Related CoMpound A;6-AMINO-2,2-DIMETHYL-5-OXOPERHYDROAZETO[2,1-B][1,3]THIAZOLE-3-CARBOXYLIC ACID;Amoxicillin Related Compound A (15 mg) ((2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid);penin;6-aps;penicin
CBNumber:
CB1410046
Molecular Formula:
C8H12N2O3S
Molecular Weight:
216.26
MOL File:
551-16-6.mol
Modify Date:
2024/6/24 22:20:23

6-Aminopenicillanic acid Properties

Melting point 198-200 °C (dec.)(lit.)
alpha 276.3 º (c=1.2, 0.1N HCl 22 ºC)
Boiling point 460.2±45.0 °C(Predicted)
Density 1.3418 (rough estimate)
refractive index 1.6300 (estimate)
storage temp. 2-8°C
solubility 2.46g/l
form Fine Powder
pka pKa 2.3 (Uncertain)
color White to cream
PH 3.4 (100g/l, H2O)
optical activity [α]22/D +276.3°, c = 1.2 in 0.1 M HCl
Water Solubility Soluble in water and hydrochoric acid.
Merck 14,458
BRN 15080
Stability Light sensitive
InChIKey NGHVIOIJCVXTGV-SDKNWNMFSA-N
LogP -3.87 at 22.5℃
CAS DataBase Reference 551-16-6(CAS DataBase Reference)
EPA Substance Registry System 6-Aminopenicillanic acid (551-16-6)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H319
Precautionary statements  P264-P280-P305+P351+P338-P337+P313
Hazard Codes  Xn
Risk Statements  42/43
Safety Statements  22-36/37-45-37-24-36
WGK Germany  2
RTECS  XH8225000
10
TSCA  Yes
HS Code  29349990
NFPA 704
0
2 0

6-Aminopenicillanic acid price More Price(5)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) A70909 (+)-6-Aminopenicillanic acid 96% 551-16-6 10G ₹3344.93 2022-06-14 Buy
Sigma-Aldrich(India) A70909 (+)-6-Aminopenicillanic acid 96% 551-16-6 50G ₹8346.08 2022-06-14 Buy
Sigma-Aldrich(India) 07307 (+)-6-Aminopenicillanic acid analytical standard 551-16-6 100MG ₹6365.1 2022-06-14 Buy
TCI Chemicals (India) A0800 6-Aminopenicillanic Acid 551-16-6 5G ₹2000 2022-05-26 Buy
TCI Chemicals (India) A0800 6-Aminopenicillanic Acid 551-16-6 25G ₹3500 2022-05-26 Buy
Product number Packaging Price Buy
A70909 10G ₹3344.93 Buy
A70909 50G ₹8346.08 Buy
07307 100MG ₹6365.1 Buy
A0800 5G ₹2000 Buy
A0800 25G ₹3500 Buy

6-Aminopenicillanic acid Chemical Properties,Uses,Production

Chemical Properties

WHITE TO CREAM FINE POWDER

Uses

(+)-6-Aminopenicillanic Acid is the core structure in penicillins, obtained from the fermentation brew of the Penicillium mold. (+)-6-Aminopenicillanic Acid is used as the main starting block for the preparation of numerous semisynthetic penicillins.

Definition

ChEBI: A penicillanic acid compound having a (6R)-amino substituent. The active nucleus common to all penicillins, it may be substituted at the 6-amino position to form the semisynthetic penicillins, resulting in a variety of antibacterial and ph rmacologic characteristics.

General Description

Chemical structure: ?-lactam

Safety Profile

Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits very toxic fumes of NOx and SOx.

Purification Methods

This acid crystallises from water. [Kleppe & Stroninger J Biol Chem 254 4856 1979,Beilstein 27 III/IV 2858.]

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6-AMINO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID (+)-6-AMINOPENICILLANIC ACID 6-AMINOPENICILLANIC ACID 6-AMINO PENICILLINIC ACID 7-AMINO-3,3-DIMETHYL-6-OXO-2-THIA-5-AZABICYCLO[3.2.0]HEPTANE-4-CARBOXYLIC ACID (25,5R,6R)-6-AMINO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID (2S,5R,6R)-6-AMINO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO-[3.2.0]HEPTANE-2-CARBOXYLIC ACID aminopenicillanicacid penicin penin phenacyl6-aminopenicillinate 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, [2S-(2alpha,5alpha,6beta)]- 6-Aminopenicillanic acid;6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-APA 6-Aminopenicillanicacid,98% 6-Amino-2,2-dimethyl-5-oxoperhydroazeto[2,1-b][1,3]thiazole-3-carboxylic acid 98% 6-Aminopenicillansure 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-amino-3,3-dimethyl-7-oxo-,[2S-(2.alpha.,5.alpha.,6.beta.)] 6-AMINOPENICILLANIC ACID 99% (2S,5R,6R)-6-Amino-2,2-dimethyl-5-oxoperhydroazeto[2,1-b][1,3]thiazole-3-carboxylic acid 98% (2S,5R,6R)-6-Amino-2,2-dimethyl-5-oxoperhydroazeto[2,1-b][1,3]thiazole-3-carboxylic acid AMoxicillin IMpurity A (SulbactaM IMpurity B) Piperacillin IMpurity H Amoxicillin EP Impurity A (+)-6-Aminopenicillanic acid, >=99.0% Penicillan intermediate: penicillan core 6-Aminopenicillanic acid for synthesis (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 6-APA 6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 6-amino-2,2-dimethyl-5-oxoperhydroazeto[2,1-b][1 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-amino-3,3-dimethyl-7-oxo 5alpha,6beta)]-[2s-(2alpha 6-amino-3,3-dimethyl-7-oxo-,[2S-(2.alpha.,5.alpha.,6.beta.)]-4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid 6-aps 6-APA, (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)- (2S,5β)-6α-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid (2β,5β)-6α-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid (6R)-6-Aminopenicillanic acid 6-Aminopenicillanic acid,96% 6-AMinopenicillanic acid, 96% 25GR [2S-(2α,5α,6β)]-6-AMino-3,3-diMethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid NSC 50071 4-AMino-5-nitroso-2,6-pyriMidinediol-13C2 5-Nitroso-6-aMinouracil-13C2 6-AMino-5-nitroso-2,4(1H,3H)-pyriMidinedione-13C2 6-AMino-5-nitroso-2,4-pyriMidinediol-13C2 6-AMino-5-nitroso-22,4(1H,3H)-pyriMidinedione-13C2 6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid 6-APA 6-amino-2,2-dimethyl-5-oxoperhydroazeto[2,1-b][1 (+)-6-Aminopenicillanic acid,(2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-APA (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (6-Aminopenicillanic Acid) SulbactaM IMpurity B (AMoxicillin IMpurity A) Amoxicillin EP Impurity A(Sulbactam EP Impurity B) Sulbactam impurity B 6-aminopenicilanic acid(6-APA) Cloxacillin Impurity 3(Cloxacillin EP Impurity C) Dicloxacillin Impurity 3(Dicloxacillin EP Impurity C) Flucloxacillin Impurity 3(Flucloxacillin EP Impurity C) Piperacillin Impurity 8(EP Impurity H) Sulbactam Impurity 2(Sulbactam EP Impurity B)