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6-Aminopenicillanic acid

6-Aminopenicillanic acid
6-Aminopenicillanic acid structure
CAS No.
551-16-6
Chemical Name:
6-Aminopenicillanic acid
Synonyms
6-APA;penin;6-aps;penicin;6-Amino;NSC 50071;Sulbactam impurity B;aminopenicillanicacid;6-Aminopenicillansure;Piperacillin IMpurity H
CBNumber:
CB1410046
Molecular Formula:
C8H12N2O3S
Formula Weight:
216.26
MOL File:
551-16-6.mol

6-Aminopenicillanic acid Properties

Melting point:
198-200 °C (dec.)(lit.)
alpha 
276.3 º (c=1.2, 0.1N HCl 22 ºC)
Density 
1.3418 (rough estimate)
refractive index 
1.6300 (estimate)
storage temp. 
2-8°C
solubility 
2.46g/l
pka
pKa 2.3 (Uncertain)
form 
Fine Powder
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
InChIKey
NGHVIOIJCVXTGV-SDKNWNMFSA-N
CAS DataBase Reference
551-16-6(CAS DataBase Reference)
EPA Substance Registry System
4-Thia-1-azabicyclo[ 3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-(551-16-6)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
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
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H317 May cause an allergic skin reaction Sensitisation, Skin Category 1 Warning P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled Sensitisation, respiratory Category 1 Danger P261, P285, P304+P341, P342+P311,P501
Precautionary statements:
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P272 Contaminated work clothing should not be allowed out of the workplace.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P284 Wear respiratory protection.
P304+P340 IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P501 Dispose of contents/container to..…

6-Aminopenicillanic acid price More Price(10)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 07307 (+)-6-Aminopenicillanic acid analytical standard 551-16-6 100mg $58.7 2018-11-22 Buy
Sigma-Aldrich 1031514 Amoxicillin Related Compound A United States Pharmacopeia (USP) Reference Standard 551-16-6 15mg $1212.75 2018-11-13 Buy
TCI Chemical A0800 6-Aminopenicillanic Acid >98.0%(HPLC) 551-16-6 5g $15 2018-11-22 Buy
TCI Chemical A0800 6-Aminopenicillanic Acid >98.0%(HPLC) 551-16-6 25g $48 2018-11-22 Buy
Alfa Aesar A13056 6-Aminopenicillanic acid, 98% 551-16-6 10g $37.9 2018-11-13 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.

Enzyme inhibitor

This b-lactam (FW = 216.26 g/mol; CAS 551-16-6; Abbreviation: 6-APS), also known as 6-aminopenicillanic acid and (2S,5R,6R)-6-amino-3,3- dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, is a common starting reagent in the preparation of semi-synthetic penicillins and as an intermediate in the biosynthesis of naturally occurring penicillins. Note that 6-APS possesses no antibiotic activity on its own. 6- Aminopenicillanate is a product of the reaction catalyzed by penicillin amidase. The structure and chemistry of this metabolite was first determined by Ernst Chain, who shared the Nobel Prize in Physiology or Medicine in 1945 for his work on penicillins. Target(s): serine-type DAla- D-Ala carboxypeptidase, or penicillin-binding protein-5; Dstereospecific aminopeptidase; penicillin-binding protein-4; gaminobutyrate aminotransferase; cytosol alanyl aminopeptidase; Dalanine carboxypeptidase; penicillin amidase.

Purification Methods

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

6-Aminopenicillanic acid Preparation Products And Raw materials

Raw materials

Preparation Products


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6-Aminopenicillanic acid Spectrum


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