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Natamycin

VETRANAL®, analytical standard

Synonym: Natamycin, Pimaricin

  • CAS Number 7681-93-8

  • Empirical Formula (Hill Notation) C33H47NO13

  • Molecular Weight 665.73

  •  EC Number 231-683-5

  •  MDL number MFCD00135085

  •  PubChem Substance ID 329754196

  •  E Number E235

  •  NACRES NA.24

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Properties

Related Categories Analytical Standards, Analytical/Chromatography, E numbers (Food Additives), E200–E299 (preservatives), E235,
Quality Level   100
grade   analytical standard
product line   VETRANAL®
form   neat
shelf life   limited shelf life, expiry date on the label
application(s)   HPLC: suitable
  gas chromatography (GC): suitable
Featured Industry   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

Description

General description

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.

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 Sigma-Aldrich Chemie GmbH

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
TK3325000

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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