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Merck

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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10 G
€ 64,30
50 G
€ 180,00

About This Item

Empirische Formel (Hill-System):
C8H12N2O3S
CAS-Nummer:
Molekulargewicht:
216.26
Beilstein:
15080
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352005
PubChem Substanz-ID:
NACRES:
NA.22

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Qualitätsniveau

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

Signalwort

Warning

H-Sätze

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


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Kunden haben sich ebenfalls angesehen

6-aminopenicillanic acid.
Rolinson GN.
Chemotherapy, 2(1), 52-59 (1961)
Chromium scavenging ability of silver nanoparticles in human erythrocytes, real samples and their effect on the catalase enzyme.
Rasheed W, et al.
New. J. Chem., 40(4), 3793-3802 (2016)
An efficient nonenzymatic conversion of benzylpenicillin to 6-aminopenicillanic acid.
Weissenburger HWO and Van Der Hoeven MG.
Rec. Trav. Chim., 89(10), 1081-1084 (1970)
Anand Pai et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(48), 19810-19815 (2012-11-13)
Bacteria secrete a variety of public good exoproducts into their environment. These exoproducts are typically produced under the control of quorum sensing (QS), a signaling mechanism by which bacteria sense and respond to changes in their density. QS seems to
Syntheses of (6S)-cephalosporins from 6-aminopenicillanic acid
Fekner T, et al.
Tetrahedron, 56(33), 6053-6074 (2000)

Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    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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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    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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