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Thaxtomin A

SIGMA/SML1456 - ≥98% (HPLC)

Synonym: (3R,6S)-3-Hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]-2,5-piperazinedione; Thaxtomine A

CAS Number: 122380-18-1
Empirical Formula (Hill Notation): C22H22N4O6
Molecular Weight: 438.43
Linear Formula: C22H22N4O6
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-SML1456-1MG 1 mg
 $299.00
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assay ≥98% (HPLC)
color yellow to orange
form powder
InChI 1S/C22H22N4O6/c1-24-18(10-14-12-23-16-7-4-8-17(19(14)16)26(31)32)20(28)25(2)22(30,21(24)29)11-13-5-3-6-15(27)9-13/h3-9,12,18,23,27,30H,10-11H2,1-2H3/t18-,22-/m1/s1
InChI key QRDNJYNIEGRRKV-XMSQKQJNSA-N
Quality Level 100 
SMILES string O=C(N(C)[C@@H]1CC2=CNC3=C2C([N+]([O-])=O)=CC=C3)[C@@](CC4=CC(O)=CC=C4)(O)N(C)C1=O
storage temp. −20°C
Biochem/physiol Actions: Cellulose synthesis inhibition by thaxtomin A, indicates plant-pathogen interaction. Along with this, it also results in hypocotyls swelling and decreased seedling growth. Thaxtomin A leads to common scab disease in potato. On the whole, it attenuates cell growth and induces cell death in the infected plant.
Biochem/physiol Actions: Thaxtomin A is a nitrated diketopiperazine phytotoxin produced by Streptomyces scabies that induces plant cells necrosis. Thaxtomin A is a potent plant cellulose synthesis inhibitor.
Biochem/physiol Actions: Thaxtomin A is a phytotoxin produced by S. scabies that causes plant cell necrosis; cellulose synthesis inhibitor
General description: Thaxtomin A belongs to the class of 4-nitroindol-3-yl-containing 2,5 dioxopiperazines.
Packaging: 1 mg in glass bottle
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥98% (HPLC)
Storage Temp. −20°C
UNSPSC 12352200

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