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MedKoo Cat#: 415012 | Name: Pyrrolnitrin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pyrrolnitrin is an antifungal antibiotic isolated from Pseudomonas pyrrocinia. It is effective mainly against Trichophyton, Microsporium, Epidermophyton, and Penicillium.

Chemical Structure

Pyrrolnitrin
Pyrrolnitrin
CAS#1018-71-9

Theoretical Analysis

MedKoo Cat#: 415012

Name: Pyrrolnitrin

CAS#: 1018-71-9

Chemical Formula: C10H6Cl2N2O2

Exact Mass: 255.9806

Molecular Weight: 257.07

Elemental Analysis: C, 46.72; H, 2.35; Cl, 27.58; N, 10.90; O, 12.45

Price and Availability

Size Price Availability Quantity
1mg USD 550.00 2 Weeks
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Related CAS #
No Data
Synonym
Pyrrolnitrin; NSC107654; NSC-107654; NSC 107654
IUPAC/Chemical Name
1H-Pyrrole, 3-chloro-4-(3-chloro-2-nitrophenyl)-
InChi Key
QJBZDBLBQWFTPZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H6Cl2N2O2/c11-8-3-1-2-6(10(8)14(15)16)7-4-13-5-9(7)12/h1-5,13H
SMILES Code
O=[N+](C1=C(Cl)C=CC=C1C2=CNC=C2Cl)[O-]
Appearance
Solid powder
Purity
>97% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 257.07 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Nie C, Huang X, Xiang T, Wang Z, Zhang X. Discovery and characterization of the PpqI/R quorum sensing system activated by GacS/A and Hfq in Pseudomonas protegens H78. Microbiol Res. 2024 Oct;287:127868. doi: 10.1016/j.micres.2024.127868. Epub 2024 Aug 6. PMID: 39126862. 2: Baukova A, Bogun A, Sushkova S, Minkina T, Mandzhieva S, Alliluev I, Jatav HS, Kalinitchenko V, Rajput VD, Delegan Y. New Insights into Pseudomonas spp.-Produced Antibiotics: Genetic Regulation of Biosynthesis and Implementation in Biotechnology. Antibiotics (Basel). 2024 Jun 27;13(7):597. doi: 10.3390/antibiotics13070597. PMID: 39061279; PMCID: PMC11273644. 3: Putri VRM, Jung MH, Lee JY, Kwak MH, Mariyes TC, Kerbs A, Wendisch VF, Kong HJ, Kim YO, Lee JH. Fermentative aminopyrrolnitrin production by metabolically engineered Corynebacterium glutamicum. Microb Cell Fact. 2024 May 23;23(1):147. doi: 10.1186/s12934-024-02424-y. PMID: 38783320; PMCID: PMC11112847. 4: Awori RM, Hendre P, Amugune NO. The genome of a steinernematid-associated Pseudomonas piscis bacterium encodes the biosynthesis of insect toxins. Access Microbiol. 2023 Oct 5;5(10):000659.v3. doi: 10.1099/acmi.0.000659.v3. PMID: 37970093; PMCID: PMC10634486. 5: Mohd Din ARJ, Othman NZ. Genome sequence data of Burkholderia sp. IMCC1007 isolated from maize rhizosphere: A potential strain in fusaric acid mycotoxin biodegradation. Data Brief. 2023 May 6;48:109204. doi: 10.1016/j.dib.2023.109204. PMID: 37383771; PMCID: PMC10293998. 6: Shahid I, Han J, Hanook S, Borchers CH, El Enshasy HA, Mehnaz S. Genome mining of Pseudomonas spp. hints towards the production of under-pitched secondary metabolites. 3 Biotech. 2023 Jun;13(6):182. doi: 10.1007/s13205-023-03607-x. Epub 2023 May 12. PMID: 37193329; PMCID: PMC10182215. 7: An C, Ma S, Liu C, Ding H, Xue W. Burkholderia ambifaria XN08: A plant growth-promoting endophytic bacterium with biocontrol potential against sharp eyespot in wheat. Front Microbiol. 2022 Jul 28;13:906724. doi: 10.3389/fmicb.2022.906724. PMID: 35966702; PMCID: PMC9368319. 8: Arrebola E, Aprile FR, Calderón CE, de Vicente A, Cazorla FM. Insecticidal features displayed by the beneficial rhizobacterium Pseudomonas chlororaphis PCL1606. Int Microbiol. 2022 Nov;25(4):679-689. doi: 10.1007/s10123-022-00253-w. Epub 2022 Jun 7. PMID: 35670867; PMCID: PMC9526686. 9: Alvarez F, Simonetti E, Draghi WO, Vinacour M, Palumbo MC, Do Porto DF, Montecchia MS, Roberts IN, Ruiz JA. Genome mining of Burkholderia ambifaria strain T16, a rhizobacterium able to produce antimicrobial compounds and degrade the mycotoxin fusaric acid. World J Microbiol Biotechnol. 2022 May 17;38(7):114. doi: 10.1007/s11274-022-03299-0. PMID: 35578144. 10: Chi X, Wang Y, Miao J, Wang W, Sun Y, Yu Z, Feng Z, Cheng S, Chen L, Ge Y. EppR, a new LysR-family transcription regulator, positively influences phenazine biosynthesis in the plant growth-promoting rhizobacterium Pseudomonas chlororaphis G05. Microbiol Res. 2022 Jul;260:127050. doi: 10.1016/j.micres.2022.127050. Epub 2022 Apr 29. PMID: 35504237. 11: Sati D, Joshi T, Pandey SC, Pande V, Mathpal S, Chandra S, Samant M. Identification of Putative Elicitors From Plant Root Exudates Responsible for PsoR Activation in Plant-Beneficial Pseudomonas spp. by Docking and Molecular Dynamics Simulation Approaches to Decipher Plant-Microbe Interaction. Front Plant Sci. 2022 Apr 6;13:875494. doi: 10.3389/fpls.2022.875494. PMID: 35463415; PMCID: PMC9020294. 12: Pellicciaro M, Padoan E, Lione G, Celi L, Gonthier P. Pyoluteorin Produced by the Biocontrol Agent Pseudomonas protegens Is Involved in the Inhibition of Heterobasidion Species Present in Europe. Pathogens. 2022 Mar 23;11(4):391. doi: 10.3390/pathogens11040391. PMID: 35456066; PMCID: PMC9027871. 13: Ali M, Gu T, Yu X, Bashir A, Wang Z, Sun X, Ashraf NM, Li L. Identification of the Genes of the Plant Pathogen Pseudomonas syringae MB03 Required for the Nematicidal Activity Against Caenorhabditis elegans Through an Integrated Approach. Front Microbiol. 2022 Mar 9;13:826962. doi: 10.3389/fmicb.2022.826962. PMID: 35356513; PMCID: PMC8959697. 14: Rieusset L, Rey M, Wisniewski-Dyé F, Prigent-Combaret C, Comte G. Wheat Metabolite Interferences on Fluorescent Pseudomonas Physiology Modify Wheat Metabolome through an Ecological Feedback. Metabolites. 2022 Mar 9;12(3):236. doi: 10.3390/metabo12030236. PMID: 35323679; PMCID: PMC8955329. 15: Oiki S, Yaguchi T, Urayama SI, Hagiwara D. Wide distribution of resistance to the fungicides fludioxonil and iprodione in Penicillium species. PLoS One. 2022 Jan 31;17(1):e0262521. doi: 10.1371/journal.pone.0262521. PMID: 35100282; PMCID: PMC8803201. 16: Zhou Y, Yi S, Zang Y, Yao Q, Zhu H. The Predatory Myxobacterium Citreicoccus inhibens gen. nov. sp. nov. Showed Antifungal Activity and Bacteriolytic Property against Phytopathogens. Microorganisms. 2021 Oct 12;9(10):2137. doi: 10.3390/microorganisms9102137. PMID: 34683458; PMCID: PMC8538283. 17: Liu Y, Zhou Y, Qiao J, Yu W, Pan X, Zhang T, Liu Y, Lu SE. Phenazine-1-carboxylic Acid Produced by Pseudomonas chlororaphis YL-1 Is Effective against Acidovorax citrulli. Microorganisms. 2021 Sep 23;9(10):2012. doi: 10.3390/microorganisms9102012. PMID: 34683333; PMCID: PMC8541086. 18: Schruefer S, Spadinger A, Kleinemeier C, Schmid L, Ebel F. Ypd1 Is an Essential Protein of the Major Fungal Pathogen Aspergillus fumigatus and a Key Element in the Phosphorelay That Is Targeted by the Antifungal Drug Fludioxonil. Front Fungal Biol. 2021 Oct 18;2:756990. doi: 10.3389/ffunb.2021.756990. PMID: 37744118; PMCID: PMC10512271. 19: Zaman NR, Chowdhury UF, Reza RN, Chowdhury FT, Sarker M, Hossain MM, Akbor MA, Amin A, Islam MR, Khan H. Plant growth promoting endophyte Burkholderia contaminans NZ antagonizes phytopathogen Macrophomina phaseolina through melanin synthesis and pyrrolnitrin inhibition. PLoS One. 2021 Sep 30;16(9):e0257863. doi: 10.1371/journal.pone.0257863. PMID: 34591915; PMCID: PMC8483353. 20: Chen L, Wang Y, Miao J, Wang Q, Liu Z, Xie W, Liu X, Feng Z, Cheng S, Chi X, Ge Y. LysR-type transcriptional regulator FinR is required for phenazine and pyrrolnitrin biosynthesis in biocontrol Pseudomonas chlororaphis strain G05. Appl Microbiol Biotechnol. 2021 Oct;105(20):7825-7839. doi: 10.1007/s00253-021-11600-8. Epub 2021 Sep 25. PMID: 34562115.