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Key Documents

224529

Sigma-Aldrich

3-Chloro-4-hydroxyphenylacetic acid

99%

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About This Item

Linear Formula:
ClC6H3(OH)CH2CO2H
CAS Number:
Molecular Weight:
186.59
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

powder

mp

108-110 °C (lit.)

SMILES string

OC(=O)Cc1ccc(O)c(Cl)c1

InChI

1S/C8H7ClO3/c9-6-3-5(4-8(11)12)1-2-7(6)10/h1-3,10H,4H2,(H,11,12)

InChI key

IYTUKSIOQKTZEG-UHFFFAOYSA-N

General description

3-Chloro-4-hydroxyphenylacetic acid is an auxin influx inhibitor. It is one of the major chlorinated metabolite of chlorotyrosine.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

Certificates of Analysis (COA)

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Petr Hosek et al.
Journal of experimental botany, 63(10), 3815-3827 (2012-03-23)
The molecular basis of cellular auxin transport is still not fully understood. Although a number of carriers have been identified and proved to be involved in auxin transport, their regulation and possible activity of as yet unknown transporters remain unclear.
Ali R Mani et al.
The Journal of biological chemistry, 282(40), 29114-29121 (2007-08-10)
During inflammation, neutrophil- and monocyte-derived myeloperoxidase catalyzes the formation of hypochlorous acid, which can chlorinate tyrosine residues in proteins to form chlorotyrosine. However, little is known of the metabolism and disposition of chlorotyrosine in vivo. Following infusion of deuterium-labeled [D(4)]chlorotyrosine
B A van de Pas et al.
Applied and environmental microbiology, 67(9), 3958-3963 (2001-08-30)
The amount of energy that can be conserved via halorespiration by Desulfitobacterium dehalogenans JW/IU-DC1 was determined by comparison of the growth yields of cells grown with 3-chloro-4-hydroxyphenyl acetate (Cl-OHPA) and different electron donors. Cultures that were grown with lactate, pyruvate
H Nguyen et al.
Toxicology, 160(1-3), 207-217 (2001-03-14)
Exposure to airborne pollutants such as tobacco smoke is associated with increased activation of inflammatory-immune processes and is thought to contribute to the incidence of respiratory tract disease. We hypothezised that cigarette smoke (CS) could synergize with activated inflammatory/immune cells
I Utkin et al.
Applied and environmental microbiology, 61(1), 346-351 (1995-01-01)
Resting cells of Desulfitobacterium dehalogenans JW/IU-DC1 growth with pyruvate and 3-chloro-4-hydroxyphenylacetate (3-Cl-4-OHPA) as the electron acceptor and inducer of dehalogenation reductively ortho-dehalogenate pentachlorophenol (PCP); tetrachlorophenols (TeCPs); the trichlorophenols 2,3,4-TCP, 2,3,6-TCP, and 2,4,6-TCP; the dichlorophenols 2,3-DCP, 2,4-DCP, and 2,6-DCP; 2,6-dichloro-4-R-phenols (2,6-DCl-4-RPs

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