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Natamycin

VETRANAL®, analytical standard

Synonyme(s) :

Pimaricin, Natamycin

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About This Item

Formule empirique (notation de Hill):
C33H47NO13
Numéro CAS:
Poids moléculaire :
665.73
Numéro CE :
Numéro MDL:
Code UNSPSC :
41116107
ID de substance PubChem :
Numéro E:
E235
Nomenclature NACRES :
NA.24

Qualité

analytical standard

Niveau de qualité

Gamme de produits

VETRANAL®

Durée de conservation

limited shelf life, expiry date on the label

Technique(s)

HPLC: suitable
gas chromatography (GC): suitable

Application(s)

cleaning products
cosmetics
food and beverages
personal care

Format

neat

Température de stockage

2-8°C

Chaîne 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

Clé InChI

NCXMLFZGDNKEPB-FFPOYIOWSA-N

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Description générale

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.

Application

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.

Actions biochimiques/physiologiques

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

Informations légales

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3


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Consulter la Bibliothèque de documents

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)
Natamycin as a fungicide in agar media.
Pedersen, Jens Christian.
Applied and Environmental Microbiology, 58 (3), 1064-1066 (1992)
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)
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)
R S Bhatta et al.
International journal of pharmaceutics, 432(1-2), 105-112 (2012-05-10)
The aim of this study was to prepare natamycin encapsulated lecithin/chitosan mucoadhesive nanoparticles (NPs) for prolonged ocular application. These NPs were characterized by their mean particle size 213nm, encapsulation efficiency 73.57%, with a theoretical drug loading 5.09% and zeta potential

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