Natamycin

Name: Natamycin
SKU: N0075
Availability: InStock

Product ID N0075

Cas No. 7681-93-8

Purity ≥98%

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Description

Natamycin is a polyene macrolide found in Streptomyces natalensis that exhibits antifungal and immunostimulatory activities; this compound binds ergosterol, inhibiting membrane fusion. Natamycin is an antimicrobial compound that is clinically used to treat keratitis, displaying great efficacy against Aspergillus and Fusarium. Natamycin increases activation of the NALP3 inflammasome and secretion of IL-1β by inducing K+ efflux in dendritic cells; it also activates polyclonal B cells in mouse lymphocytes. Additionally, natamycin is used to improve the shelf life of cheese.

Product Info

Cas No.	7681-93-8
Purity	≥98%
Formula	C₃₃H₄₇NO₁₃
Formula Wt.	665.73
Chemical Name	16-(3-Amino-3,6-didesoxy-beta-D-mannopyranosyloxy)-5,6- epoxy-8,12,14-trihydroxy-26-methyl-2,10-dioxo-1- oxacyclohexacosa-3,17,19,21,23-pentaen-13-carbonsaeure
IUPAC Name	(1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
Synonym	Pimaricin, Tennecetin, Mycophyt, Myprozine, Natacyn, Pimafucin.
Melting Point	280-300°C (dec)
Solubility	Soluble at 20oC in 87% glycerol (0.18g/mL). Practically insoluble in higher alcohols.
Appearance	White to yellow crystalline powder

Shipping and Storage

Store Temp	4°C
Ship Temp	Ambient

Downloads

MSDS	N0075 MSDS PDF
Info Sheet	N0075 Info Sheet PDF

References

Kallinteri LD, Kostoula OK, Savvaidis IN. Efficacy of nisin and/or natamycin to improve the shelf-life of Galotyri cheese. Food Microbiol. 2013 Dec;36(2):176-81. PMID: 24010596.

Thomas PA, Kaliamurthy J. Mycotic keratitis: epidemiology, diagnosis and management. Clin Microbiol Infect. 2013 Mar;19(3):210-20. PMID: 23398543.

Darisipudi MN, Allam R, Rupanagudi KV, et al. Polyene macrolide antifungal drugs trigger interleukin-1β secretion by activating the NLRP3 inflammasome. PLoS One. 2011;6(5):e19588. PMID: 21625424.

Hammarström L, Smith CI. In vitro activating properties of polyene antibiotics for murine lymphocytes. Acta Pathol Microbiol Scand C. 1977 Aug;85C(4):277-83. PMID: 302553.