A tetraene macrolide with fungicidal activities
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Natamycin

Item No. 11634

Technical Information
Formal Name
(5R,7R,24S)-22R-[(3S-amino-3,6-dideoxy-β-D-mannopyranosyl)oxy]-1R,3S,26S-trihydroxy-12R-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8E,14E,16E,18E,20E-pentaene-25R-carboxylic acid
CAS Number
7681-93-8
Synonyms
  • Antibiotic A 5283
  • CL 12,625
  • Delvocid
  • E 235
  • Mycophyt
  • Myprozine
  • Pimaricin
  • Synogil
  • Tennecetin
Molecular Formula
C33H47NO13
Formula Weight
Purity
≥95%
A crystalline solid
DMSO: 1 mg/mlMethanol: 1 mg/ml
λmax
219, 290, 303, 317 nm
SMILES
O=C(O[C@H](C)C/C=C/C=C/C=C/C=C/[C@H](O[C@@]1([H])[C@@H](O)[C@@H](N)[C@H](O)[C@@H](C)O1)C[C@]([C@H](C(O)=O)[C@@H](O)C2)([H])O[C@]2(O)C[C@@H](O)C3)/C=C/[C@@H]4[C@@H]3O4
InChi Code
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-
InChi Key
NCXMLFZGDNKEPB-FFPOYIOWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Natamycin is a tetraene macrolide that has been found in S. natalensis and has fungicidal activities.1,2,3 It is active against Fusarium, A. flavus, and A. fumigatus clinical isolates (MIC50s = 4, 32, and 2 µg/ml, respectively), and the plant pathogenic fungi B. cinerea and P. expansum when used at a concentration of 2 mg/L.1,2 Natamycin (100 and 200 mg/L, respectively) inhibits B. cinerea-induced gray mold disease in grapes and P. expansum-induced blue mold disease in jujube fruit.2 It reduces ulceration, edema, swelling, iritis, white blood cell accumulation, and loss of corneal transparency, as well as prevents F. solani-induced ocular keratitis, in a rabbit model of fungal keratitis.3 Formulations containing natamycin have been used in the treatment of fungal blepharitis, conjunctivitis, and keratitis, and as fungicides in agricultural settings and as food additives.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lalitha, P., Vijaykumar, R., Prajna, N.V., et alIn vitro natamycin susceptibility of ocular isolates of Fusarium and Aspergillus species: Comparison of commercially formulated natamycin eye drops to pharmaceutical-grade powder. J. Clin. Microbiol. 46(10), 3477-3478 (2008).

    2. He, C., Zhang, Z., Li, B., et alEffect of natamycin on Botrytis cinerea and Penicillium expansum—Postharvest pathogens of grape berries and jujube fruit. Postharvest Bio. Technol. 151, 134-141 (2019).

    3. Dong, X.H., Gao, W.J., and He, X.P. Antifungal efficacy of natamycin in experimental fusarium solani keratitis. Int. J. Ophthalmol. 5(2), 143-146 (2012).