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SML0447

Sigma-Aldrich

3-Chloro-5-hydroxybenzoic acid

≥97% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C7H5ClO3
CAS Number:
53984-36-4
Molecular Weight:
172.57
MDL number:
MFCD04114327
UNSPSC Code:
12352200
PubChem Substance ID:
329824729

Assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL (clear solution)

storage temp.

room temp

SMILES string

Oc1cc(Cl)cc(c1)C(O)=O

InChI

1S/C7H5ClO3/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,9H,(H,10,11)

InChI key

RJOLIYHZZKAIET-UHFFFAOYSA-N

Biochem/physiol Actions

3-Chloro-5-hydroxybenzoic acid is a selective agonist of the lactate receptor, GPR81. Stimulation of either GPR81 or GPR109a in adipose tissue leads to a similar decrease in triglyceride lipolysis. Niacin is used to treat dyslipidemia via its agonism of GPR109a, but compliance is low due to side effects (flushing and pruritus), which are associated with GPR109a agonism. 3-Chloro-5-hydroxybenzoic acid is selective for GPR81 over other GPCRs, including GPR109a. While less potent than niacin (16 vs. 0.78 μM), it has similar activity as the same dose as niacin in animal studies and should not cause the flushing that is associated with niacin.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H315,H318,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Timothy P Brown et al.
Oncogene, 39(16), 3292-3304 (2020-02-20)
GPR81 is a G-protein-coupled receptor for lactate, which is upregulated in breast cancer and plays an autocrine role to promote tumor growth by tumor cell-derived lactate. Here we asked whether lactate has any paracrine role via activation of GPR81 in
Marvin Lambertus et al.
Acta physiologica (Oxford, England), 231(3), e13587-e13587 (2020-11-28)
Adult neurogenesis occurs in two major niches in the brain: the subgranular zone of the hippocampal formation and the ventricular-subventricular zone. Neurogenesis in both niches is reduced in ageing and neurological disease involving dementia. Exercise can rescue memory by enhancing
Rafaz Hoque et al.
Gastroenterology, 146(7), 1763-1774 (2014-03-25)
The NACHT, LRR, and pyrin domain-containing protein 3 (NLRP3) inflammasome induces inflammation in response to organ injury, but little is known about its regulation. Toll-like receptors (TLRs) provide the first signal required for activation of the inflammasome and stimulate aerobic
Haíssa de Castro Abrantes et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 39(23), 4422-4433 (2019-03-31)
The discovery of a G-protein-coupled receptor for lactate named hydroxycarboxylic acid receptor 1 (HCAR1) in neurons has pointed to additional nonmetabolic effects of lactate for regulating neuronal network activity. In this study, we characterized the intracellular pathways engaged by HCAR1

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