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32417

Natamycin

VETRANAL®, analytical standard

Synonym(s):

Pimaricin, Natamycin

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About This Item

Empirical Formula (Hill Notation):
C33H47NO13
CAS Number:
7681-93-8
Molecular Weight:
665.73
E Number:
E235
PubChem Substance ID:
329754196
UNSPSC Code:
41116107
NACRES:
NA.24
EC Number:
231-683-5
MDL number:
MFCD00135085
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grade

analytical standard

Quality Segment

100

product line

VETRANAL®

shelf life

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

storage temp.

2-8°C

SMILES string

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

InChI key

NCXMLFZGDNKEPB-FFPOYIOWSA-N

General description

Natamycin shows activity against both molds and yeasts. It finds applications as a fungicidal and antibiotic preservative in the food industry.
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.

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.

Biochem/physiol Actions

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

Legal Information

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

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Storage Class

11 - Combustible Solids

wgk

WGK 3

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