3-CHLORO-5-HYDROXY-BENZOIC ACID

3-CHLORO-5-HYDROXY-BENZOIC ACID
  • CAS No.:53984-36-4

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  1. This product is a chemical product/pharmaceutical intermediate. It is not a drug, an active pharmaceutical ingredient (API), or a pharmaceutical-grade material. It has not been granted a drug approval number or a Chemical Drug Substance Approval Notice, has not passed drug-related review and approval, and is not manufactured, tested, or released in accordance with pharmaceutical GMP.
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3-CHLORO-5-HYDROXY-BENZOIC ACID Basic information
Product Name:3-CHLORO-5-HYDROXY-BENZOIC ACID
Synonyms:3-CHLORO-5-HYDROXY-BENZOIC ACID;5-(hydroxy)-3-chlorobenzoic acid;5-Chloro-m-salicylic Acid;3-chloro-5-hydroxy BA;Benzoic acid, 3-chloro-5-hydroxy-;GPR81 Agonist, 3Cl-5OH-BA;GPR81 Agonist, 3Cl-5OH-BA - CAS 53984-36-4 - Calbiochem
CAS:53984-36-4
MF:C7H5ClO3
MW:172.57
EINECS:
Product Categories:Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Carboxylic Acids;Phenyls & Phenyl-Het
Mol File:53984-36-4.mol
3-CHLORO-5-HYDROXY-BENZOIC ACID Chemical Properties
Melting point 244.0 to 248.0 °C
Boiling point 364.8±27.0 °C(Predicted)
density 1.536±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
solubility DMSO: soluble15mg/mL (clear solution)
pka3.71±0.10(Predicted)
form powder
color white to beige
InChIKeyRJOLIYHZZKAIET-UHFFFAOYSA-N
CAS DataBase Reference53984-36-4
Safety Information
Hazard Codes Xn
Risk Statements 22-37/38-41
Safety Statements 26-36
WGK Germany 3
HS Code 2916399090
MSDS Information
3-CHLORO-5-HYDROXY-BENZOIC ACID Usage And Synthesis
Uses5-Chloro-m-salicylic Acid was studied as a potential selective lactate receptor (GPR81) agonists with antilipolytic effects.
UsesGPR81, also known as hydroxycarboxylic acid receptor 1 (HCAR1), is a recently de-orphanized receptor that is activated by lactic acid (EC50 ~ 1.5 mM) but not by other hydroxycarboxylic acids. 3-chloro-5-hydroxy Benzoic Acid (3-chloro-5-hydroxy BA) is an agonist of GPR81 (EC50 = 16 μM) that is inactive against the related GPR109a (HCAR2) receptor. It is similarly effective at GPR81 receptors from a variety of mammalian species and is bioavailable, stimulating lipolysis (increased serum free fatty acids) in mice fed high fat chow for 10 weeks. 3-chloro-5-hydroxy BA, like lactate, blocks basal ghrelin secretion by primary gastric mucosal cells.[Cayman Chemical]
Biological Activity3-chloro-5-hydroxy ba is a gpr81 agonist.gpr81 (hca1) is a member of g-protein-coupled receptors (gpcrs). gpr81 is predominantly expressed on adipocytes and is activated by the endogenous ligands 2-hydroxypropanoate (lactate). stimulation of gpr81 in adipose tissue lead to a decrease in the lipolysis of triglycerides by hormone-sensitive lipase, which resulted in reduced transport of fatty acids to the liver and a decrease in hepatic triglycerides [1].
in vitroin the hgpr81 assay, 3-chloro-5-hydroxybenzoic acid showed the potency against gpr81 with an ec50 of 16 μm. the ec50 of 3-chloro-5-hydroxybenzoic acid against monkey gpr81, dog gpr81, rat gpr81, mouse gpr81, and hamster gpr81 was 17 μm, 67 μm, 7 μm, 22 μm and 27 μm, respectively [1]. 3-chloro-5-hydroxy ba blocked basal ghrelin secretion by primary gastric mucosal cells [2].
in vivoin mice, oral administration of 3-chloro-5-hydroxybenzoic acid at 30 mg/kg provided a cmax of 67 μm at approximately 3-fold over the in vitro ec50 with an aucinf of 54 h μm and a short t1/2 of 1.5 h, and the 100 mg/kg p.o dose attained a cmax of 342 μm at greater than 15-fold over the observed in vitro ec50 [1].
references[1]. dvorak c a, liu c, shelton j, et al. identification of hydroxybenzoic acids as selective lactate receptor (gpr81) agonists with antilipolytic effects[j]. acs medicinal chemistry letters, 2012, 3(8): 637-639.[2]. engelstoft m s, park w, sakata i, et al. seven transmembrane g protein-coupled receptor repertoire of gastric ghrelin cells[j]. molecular metabolism, 2013, 2(4): 376-392.
3-CHLORO-5-HYDROXY-BENZOIC ACID Preparation Products And Raw materials

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