P9703

Pimaricin

from Streptomyces chattanoogensis, ≥95% (HPLC)

• Synonym(s): Natamycin
• Empirical Formula (Hill Notation): C₃₃H₄₇NO₁₃
• CAS Number: 7681-93-8
• Molecular Weight: 665.73
• EC Number: 231-683-5
• MDL number: MFCD00135085
• UNSPSC Code: 51101500
• PubChem Substance ID: 24899055
• NACRES: NA.85

Properties

• biological source: Streptomyces chattanoogensis
• Quality Level: 300
• Assay: ≥95% (HPLC)
• form: lyophilized powder; powder
• solubility: 0.1% formic acid in methanol: soluble 1 mg/mL
• antibiotic activity spectrum: fungi
• application(s): agriculture; environmental
• Mode of action: cell membrane | interferes
• 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

Chemical structure: macrolide

Application

Pimaricin is an amphoteric antibiotic from Streptomyces chattanoogensis. It is used for a variety of fungal infections, mainly topically. It is used as an ergosterol and cholesterol binding agent to study lipid bilayer dynamics, especially in fungal cells. Pimaricin is used as a fungicide in agar media. It is used to study the pleitropic regulator AdpAch and the gamma-butyrolactone regulatory system of Streptomyces chattanoogensis.

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

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: 2 - 8 °C. Light sensitive.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves