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P8861

Sigma-Aldrich

Pyrrolnitrin from Pseudomonas cepacia

≥98% (HPLC), solid

Synonym(s):

3-Chloro-4-(3-chloro-2-nitrophenyl)pyrrole

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About This Item

CAS Number:
1018-71-9
EC Number:
213-812-7
MDL number:
MFCD00865605
UNSPSC Code:
12352200
PubChem Substance ID:
24898985
NACRES:
NA.77

Quality Level

200

Assay

≥98% (HPLC)

form

solid

antibiotic activity spectrum

fungi

Mode of action

enzyme | inhibits

shipped in

wet ice

storage temp.

−20°C

SMILES string

[O-][N+](=O)c1c(Cl)cccc1-c2c[nH]cc2Cl

InChI

1S/C10H6Cl2N2O2/c11-8-3-1-2-6(10(8)14(15)16)7-4-13-5-9(7)12/h1-5,13H

InChI key

QJBZDBLBQWFTPZ-UHFFFAOYSA-N

Specificity

The purified antibiotic has strong antifungal activity and is less efficient against bacteria or yeast.

Application

Pyrrolnitrin from Pseudomonas cepacia has been used as a standard in the detection of pyrrolnitrin in Serratia marcescens cell culture extract.

Biochem/physiol Actions

Pyrrolnitrin blocks the terminal electron transport between succinate or reduced NADH and coenzyme Q. In mitochondria preparations of S. cerevisiae, the antibiotic inhibited succinate oxidase, NADH oxidase, succinate cythochrome C reductase, and NADH-cytochrome C reductase. Pyrrolnitrin is involved in many cellular processes such as oxidative stress, electron transport, DNA and RNA synthesis.
Pyrrolnitrin is a metabolite, produced by Pseudomonas sp.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

P8861-1MG:
P8861-1MG-PW:
P8861-VAR:
P8861-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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El-Banna, N., and Winkelmann, G.
Applied Microbiology, 85, 69-69 (1998)
Suppression of damping-off of cucumber caused by Pythium ultimum with live cells and extracts of Serratia marcescens N4-5
Roberts DP, et al.
Soil Biology and Biochemistry, 39(9), 2275-2288 (2007)
Chernin, L., et al.
Current Microbiology, 32, 208-208 (1996)
Magdalena M Rose et al.
Environmental microbiology, 23(9), 5525-5540 (2021-08-05)
The unicellular alga Chlamydomonas reinhardtii and the bacterium Pseudomonas protegens serve as a model to study the interactions between photosynthetic and heterotrophic microorganisms. P. protegens secretes the cyclic lipopeptide orfamide A that interferes with cytosolic Ca2+ homeostasis in C. reinhardtii
Natural Antimicrobials for the Minimal Processing of Foods, 201-201 (2003)

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