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57310

Sigma-Aldrich

Indole-3-butyric acid

≥98.0% (T)

Synonym(s):

4-(3-Indolyl)butanoic acid, 4-(3-Indolyl)butyric acid, IBA

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About This Item

Empirical Formula (Hill Notation):
C12H13NO2
CAS Number:
133-32-4
Molecular Weight:
203.24
Beilstein/REAXYS Number:
171120
EC Number:
205-101-5
MDL number:
MFCD00005664
UNSPSC Code:
12352106
PubChem Substance ID:
57651621
NACRES:
NA.77
assay:
≥98.0% (T)

Quality Level

100

assay

≥98.0% (T)

mp

122-125 °C

SMILES string

OC(=O)CCCc1c[nH]c2ccccc12

InChI

1S/C12H13NO2/c14-12(15)7-3-4-9-8-13-11-6-2-1-5-10(9)11/h1-2,5-6,8,13H,3-4,7H2,(H,14,15)

InChI key

JTEDVYBZBROSJT-UHFFFAOYSA-N

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Application

Indole-3-butyric acid (IBA) has been used as a standard to monitor IBA in urine samples by tandem mass spectrometry-selected reaction monitoring (SRM) and Ultra-high performance liquid chromatography (UHPLC), as a standard for high performance liquid chromatography (HPLC) for the quantification of IBA in foliar tissues of Coffea canephora seedlings.

Biochem/physiol Actions

Indole-3-butyric acid (IBA) is a naturally occurring phytohormone auxin (plant growth regulator). It promotes root formation in cuttings but does not affect ethylene levels. IBA might be a precursor for indole-3-acetic acid (IAA) through β oxidation pathway. IBA is present in plant species like Zea mays, Pisum sativum and Arabidopsis. IBA is more potent than IAA for inducing root formation.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM6534
BCCL3417
BCCJ2755
BCCK6356
BCCF4147

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Transport of the two natural auxins, indole-3-butyric acid and indole-3-acetic acid, in Arabidopsis
Rashotte AM, et al.
Plant Physiology, 133(2), 761-772 (2003)
Dynamics of the concentration of IAA and some of its conjugates during the induction of somatic embryogenesis in Coffea canephora
Ayil-Gutierrez B, et al.
Plant signaling & behavior, 8(11), e26998-e26998 (2013)
K W Mudge et al.
Plant physiology, 61(2), 271-273 (1978-02-01)
Light-grown mung bean (Phaseolus aureus Roxb.) cuttings were treated with buffered and nonbuffered solutions of Ethephon, indole butyric acid (IBA), and the combination of both. Ethephon treatment resulted in increased tissue ethylene levels with increasing solution pH, but had no
Joohyun Kang et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(5), 2355-2360 (2010-02-06)
Abscisic acid (ABA) is a ubiquitous phytohormone involved in many developmental processes and stress responses of plants. ABA moves within the plant, and intracellular receptors for ABA have been recently identified; however, no ABA transporter has been described to date.
Tereza Pavlova et al.
Analytica chimica acta, 987, 72-80 (2017-09-17)
While over 10% of the human metabolome is directly associated with the gut microbial metabolism, specific metabolites are largely uncharacterized. Therefore, methods for the identification and quantification of microbiota-associated metabolites in biological fluids such as urine or plasma are necessary
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