Pimaricin (also known as natamycin, INN) is a naturally occurring antifungal agent obtained through the fermentation of Streptomyces natalensis. It belongs to the macrolide polyene class of antifungals and is commonly used in the treatment of fungal keratitis, an eye infection. In the medical field, it is effective against a wide range of fungal infections caused by Candida, Aspergillus, Cephalosporium, Fusarium, and Penicillium. In the food industry, pimaricin is widely applied as a natural preservative to prevent fungal contamination. Its mechanism of action involves binding to ergosterol in the fungal plasma membrane, disrupting ergosterol-dependent vacuole and membrane fusion, thereby suppressing fungal growth. Additionally, it inhibits amino acid and glucose transport by interfering with membrane transport proteins.
| Product Name: | Natamycin |
| Synonyms: | NataMycin, A 5283, Delvolan, Delvocid, Myprozine, Natacyn, Natafucin, PiMafucin, PiMafugin, A5263, CL 12625, E235;Natamycin(FermentionProcess);(1R*,3S*,5R*,7R*,8E,12R*,14E,16E,18E,20E,22R*,24S*,25R*,26S*)]-22-[(3-Amino-3,6-dideoxy-β-D-mannopyranosyl)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;NATAMYCIN;PIMAFUCIN;PIMARICIN;PIMARICIN, STREPTOMYCES CHATTANOOGENSIS;antibiotica-5283 |
| CAS: | 7681-93-8 |
| MF: | C33H47NO13 |
| MW: | 665.73 |
| EINECS: | 231-683-5 |
| Product Categories: | Food additives;Food & Feed ADDITIVES;Antifungal (Topical);Intermediates & Fine Chemicals;Pharmaceuticals;ERGOSTAT;antibiotic;raw materials;Food additive;7681-93-8 |
| Mol File: | 7681-93-8.mol |
Natamycin Chemical Properties
| Melting point | 2000C (dec) |
| Alpha | D20 +278° (c = 1 in CH3COOH) |
| Boiling point | 952℃ |
| Density | 1.0 g/mL at 20 °C(lit.) |
| Bulk density | 200kg/m3 |
| Refractive index | 1.5960 (estimate) |
| Fp | >110°(230°F) |
| Storage temp | Keep in dark place,Inert atmosphere,2-8°C |
| Solubility | Soluble in DMSO |
| Form | Aqueous suspension |
| Pka | PKa 4.6(50% aq. MeOEtOH) (Uncertain);8.35 (Uncertain) |
| Color | Cream colored |
| Water Solubility | 0.41g/L(21 ºC) |
| Sensitive | Light Sensitive |
| Merck | 13,6453 |
| BRN | 1614878 |
| Stability | Light sensitive |
| InChIKey | NCXMLFZGDNKEPB-FFPOYIOWSA-N |
| LogP | 0.880 (est) |
| EPA Substance Registry System | 6,11,28-Trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid, 22-[(3-amino-3,6-dideoxy-.beta.-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)- (7681-93-8) |
Pimaricin is used as a preservative coating on the surface of Italian cheeses to inhibit mold and yeast growth. It is tasteless, odorless, colorless, and does not penetrate into the cheese. Highly effective against nearly all molds and yeasts, it leaves bacteria unaffected, ensuring the natural ripening and flavor development of the cheese. Application methods include dipping, spraying, or incorporation into cheese coatings, with usage levels typically ranging from 300 to 2,000 ppm.
