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Merck
CN

SML3231

Auxinole

≥98% (HPLC), auxin antagonist, powder

Synonym(s):

α-[2,4-dimethylphenylethyl-2-oxo]-IAA, α-[2-(2,4-Dimethylphenyl)-2-oxoethyl]-1H-indole-3-acetic acid

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About This Item

Empirical Formula (Hill Notation):
C20H19NO3
CAS Number:
86445-22-9
Molecular Weight:
321.37
UNSPSC Code:
12352107
NACRES:
NA.77
MDL number:
MFCD31657391

Key Documents

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Product Name

Auxinole, ≥98% (HPLC)

InChI

1S/C20H19NO3/c1-12-7-8-14(13(2)9-12)19(22)10-16(20(23)24)17-11-21-18-6-4-3-5-15(17)18/h3-9,11,16,21H,10H2,1-2H3,(H,23,24)

InChI key

HGUYAIJBXSQXGV-UHFFFAOYSA-N

SMILES string

O=C(C(C1=CNC2=C1C=CC=C2)CC(C3=C(C=C(C=C3)C)C)=O)O

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Auxinole is a potent auxin antagonist that binds to SCF(TIR1) and blocks TIR1-IAA-Aux/IAA complex formation thereby inhibiting auxin-responsive gene expression.
potent auxin antagonist that binds to SCF(TIR1)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000468851
0000468850
0000468850
0000401412
0000401412

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Julian Dindas et al.
Nature communications, 9(1), 1174-1174 (2018-03-23)
Auxin is a key regulator of plant growth and development, but the causal relationship between hormone transport and root responses remains unresolved. Here we describe auxin uptake, together with early steps in signaling, in Arabidopsis root hairs. Using intracellular microelectrodes
Ken-ichiro Hayashi et al.
ACS chemical biology, 7(3), 590-598 (2012-01-12)
The plant hormone auxin is a master regulator of plant growth and development. By regulating rates of cell division and elongation and triggering specific patterning events, indole 3-acetic acid (IAA) regulates almost every aspect of plant development. The perception of
Veronika Smékalová et al.
The New phytologist, 203(4), 1175-1193 (2014-06-14)
The role of YODA MITOGEN ACTIVATED PROTEIN KINASE KINASE KINASE 4 (MAPKKK4) upstream of MITOGEN ACTIVATED PROTEIN KINASE 6 (MPK6) was studied during post-embryonic root development of Arabidopsis thaliana. Loss- and gain-of-function mutants of YODA (yda1 and ΔNyda1) were characterized

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