Skip to Content
Merck
CN

SML1456

Thaxtomin A

≥98% (HPLC)

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C22H22N4O6
CAS Number:
122380-18-1
Molecular Weight:
438.43
UNSPSC Code:
12352200
PubChem Substance ID:
329825893
NACRES:
NA.77

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

Thaxtomin A, ≥98% (HPLC)

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

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

assay

≥98% (HPLC)

form

powder

color

yellow to orange

storage temp.

−20°C

Quality Level

100

Related Categories

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.
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.
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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000421851
0000421851
0000415313
0000415313
0000143919

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Xuejin Zhao et al.
Synthetic and systems biotechnology, 7(3), 972-981 (2022-06-28)
The application of the valuable natural product thaxtomin A, a potent bioherbicide from the potato scab pathogenic Streptomyces strains, has been greatly hindered by the low yields from its native producers. Here, we developed an orthogonal transcription system, leveraging extra-cytoplasmic
Thaxtomin A induces programmed cell death in Arabidopsis thaliana suspension-cultured cells
Duval I, et al.
Planta, 222(5), 820-831 (2005)
Multiplexed Promoter Engineering for Improving Thaxtomin A Production in Heterologous Streptomyces Hosts.
Zhao, et al.
Life (Basel, Switzerland), 12 (2022)
Thaxtomin A affects CESA-complex density, expression of cell wall genes, cell wall composition, and causes ectopic lignification in Arabidopsis thaliana seedlings
Bischoff V, et al.
Journal of Experimental Botany, 60(3), 955-965 (2009)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service