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A70909

Sigma-Aldrich

(+)-6-Aminopenicillansäure

96%

Synonym(e):

(2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-carbonsäure, 6-APA

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64,30 €
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179,00 €

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10 G
64,30 €
50 G
179,00 €

About This Item

Empirische Formel (Hill-System):
C8H12N2O3S
CAS-Nummer:
551-16-6
Molekulargewicht:
216.26
Beilstein:
15080
EG-Nummer:
208-993-4
MDL-Nummer:
MFCD00005176
UNSPSC-Code:
12352005
PubChem Substanz-ID:
24891174
NACRES:
NA.22

64,30 €

Versandbereit am22. April 2025Details

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Qualitätsniveau

200

Assay

96%

Form

powder

Optische Aktivität

[α]22/D +276.3°, c = 1.2 in 0.1 M HCl

mp (Schmelzpunkt)

198-200 °C (dec.) (lit.)

Wirkungsspektrum von Antibiotika

Gram-positive bacteria

Wirkungsweise

cell wall synthesis | interferes

Lagertemp.

2-8°C

SMILES String

CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O

InChI

1S/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

InChIKey

NGHVIOIJCVXTGV-ALEPSDHESA-N

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Allgemeine Beschreibung

(+)-6-Aminopenicillanic acid is the core moiety of different penicillins.[1] It can be prepared from the benzylpenicillin silyl ester via cleavage of the amide bond.[2] The coating of (+)-6-aminopenicillanic acid on silver nanoparticles (6APA-AgNPs), imparts them with an ability to detect chromium (IV) in human erythrocytes.[3]
Chemical structure: ß-lactam

Anwendung

(+)-6-Aminopenicillanic acid can be used as a starting material for the synthesis of (6S,7S)-cephalosporins,[4] and organotin polyamine esters by reacting with organotin dihalides via interfacial polycondensation.[5]
It reacts with higher amino acid Schiff bases to form the corresponding β-lactam derivatives.4

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H319

Gefahreneinstufungen

Eye Irrit. 2

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 2

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
MKCV2440
MKCS9569
0000225871
MKCS6257
08708AJ

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Phenoxyessigsäure 98%

Sigma-Aldrich

158518

Phenoxyessigsäure

Amoxicillin-verwandte Verbindung I United States Pharmacopeia (USP) Reference Standard

USP

1031591

Amoxicillin-verwandte Verbindung I

2-Hydroxyphenylessigsäure ReagentPlus®, 99%

Sigma-Aldrich

H49804

2-Hydroxyphenylessigsäure

Organotin polyamine esters from reaction of 6-aminopenicillanic acid and organotin dihalides
Carraher Jr CE, et al.
J. Polym. Mater., 29(4), 387-387 (2012)
6-aminopenicillanic acid.
Rolinson GN.
Chemotherapy, 2(1), 52-59 (1961)
Joanna Skiba et al.
European journal of medicinal chemistry, 57, 234-239 (2012-10-18)
We report on the synthesis of ferrocenyl-ampicillin and ferrocenyl-6-aminopenicillinic acid bioconjugates. Title compounds were characterized by (1)H NMR, IR, MS and elemental analysis. These novel ferrocenyl-antibiotic conjugates were also investigated by cyclic voltammetry (CV). Ferrocenyl-ampicillin complexes revealed reversible uncomplicated oxidation
Ye-Wang Zhang et al.
Applied microbiology and biotechnology, 88(1), 49-55 (2010-06-23)
A one-pot, two-step enzymatic synthesis of amoxicillin from penicillin G, using penicillin acylase, is presented. Immobilized penicillin acylase from Kluyvera citrophila was selected as the biocatalyst for its good pH stability and selectivity. Hydrolysis of penicillin G and synthesis of
David A Harris et al.
Bioorganic & medicinal chemistry letters, 19(14), 3787-3790 (2009-05-12)
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 activity of the compound and use structure-activity relationship studies
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 Antwort

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 Antwort

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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