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Merck

32417

Supelco

Natamycin

VETRANAL®, analytical standard

Sinónimos:

Pimaricin, Natamycin

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About This Item

Fórmula empírica (notación de Hill):
C33H47NO13
Número de CAS:
Peso molecular:
665.73
Número CE:
Número MDL:
Código UNSPSC:
41116107
ID de la sustancia en PubChem:
Número E:
E235
NACRES:
NA.24

grado

analytical standard

Nivel de calidad

Línea del producto

VETRANAL®

caducidad

limited shelf life, expiry date on the label

técnicas

HPLC: suitable
gas chromatography (GC): suitable

aplicaciones

cleaning products
cosmetics
food and beverages
personal care

formato

neat

temp. de almacenamiento

2-8°C

cadena SMILES

C[C@@H]1C\C=C\C=C\C=C\C=C\[C@@H](C[C@@H]2O[C@](O)(C[C@@H](O)C[C@H]3O[C@@H]3\C=C\C(=O)O1)C[C@H](O)[C@H]2C(O)=O)O[C@@H]4O[C@H](C)[C@@H](O)[C@H](N)[C@@H]4O

InChI

1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1

Clave InChI

NCXMLFZGDNKEPB-FFPOYIOWSA-N

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Descripción general

Natamycin is a polyene antibiotic that generally finds application as an antifungal agent as it lacks development of resistance and has a broad spectrum of activity. However, its mode of action is yet unclear, direct binding and isothermal titration calorimetry studies has revealed that natamycin binds specifically to ergosterol present in model membranes.
Natamycin shows activity against both molds and yeasts. It finds applications as a fungicidal and antibiotic preservative in the food industry.

Aplicación

Natamycin may be used as an analytical reference standard for the quantification of the analyte in wine samples using high-performance liquid chromatography coupled to electrospray ionization in positive mode high resolution mass spectrometry (HPLC-ESI-HR-MS) and reversed-phase high-performance liquid chromatography-tandem mass spectrometry technique (UHPLC-MS/MS).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Acciones bioquímicas o fisiológicas

An antifungal polyene macrolide that binds specifically to ergosterol and blocks fungal growth. However, unlike nysatin and filipin, pimaricin does not change the permeability of the plasma membrane

Información legal

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3


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Certificados de análisis (COA)

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Visite la Librería de documentos

Natamycin as a fungicide in agar media.
Pedersen, Jens Christian.
Applied and Environmental Microbiology, 58 (3), 1064-1066 (1992)
Natamycin blocks fungal growth by binding specifically to ergosterol without permeabilizing the membrane.
Te Welscher, Yvonne M., et al.
The Journal of Biological Chemistry, 283 (10), 6393-6401 (2008)
Development and validation of a rapid method for the determination of natamycin in wine by high-performance liquid chromatography coupled to high resolution mass spectrometry
Roberts TPD, et al.
Analytical Methods : Advancing Methods and Applications, 3(4), 937-943 (2011)
A novel and rapid method for determination of natamycin in wines based on ultrahigh-performance liquid chromatography coupled to tandem mass spectrometry: validation according to the 2002/657/EC European decision
Repizo ML, et al.
Analytical and Bioanalytical Chemistry, 402(2), 965-973 (2012)
Javier Santos-Aberturas et al.
PloS one, 7(6), e38536-e38536 (2012-06-14)
Control of polyene macrolide production in Streptomyces natalensis is mediated by the transcriptional activator PimR. This regulator combines an N-terminal domain corresponding to the Streptomyces antibiotic regulatory protein (SARP) family of transcriptional activators with a C-terminal half homologous to guanylate

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