ChemicalBook--->CAS DataBase List--->53984-36-4

53984-36-4

53984-36-4 Structure

53984-36-4 Structure
IdentificationBack Directory
[Name]

3-CHLORO-5-HYDROXY-BENZOIC ACID
[CAS]

53984-36-4
[Synonyms]

3-chloro-5-hydroxy BA
GPR81 Agonist, 3Cl-5OH-BA
5-Chloro-m-salicylic Acid
3-CHLORO-5-HYDROXY-BENZOIC ACID
5-(hydroxy)-3-chlorobenzoic acid
Benzoic acid, 3-chloro-5-hydroxy-
GPR81 Agonist, 3Cl-5OH-BA - CAS 53984-36-4 - Calbiochem
[Molecular Formula]

C7H5ClO3
[MDL Number]

MFCD04114327
[MOL File]

53984-36-4.mol
[Molecular Weight]

172.57
Chemical PropertiesBack Directory
[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. ]

room temp
[solubility ]

DMSO: soluble15mg/mL (clear solution)
[form ]

powder
[pka]

3.71±0.10(Predicted)
[color ]

white to beige
[InChIKey]

RJOLIYHZZKAIET-UHFFFAOYSA-N
[CAS DataBase Reference]

53984-36-4
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

22-37/38-41
[Safety Statements ]

26-36
[WGK Germany ]

3
[HS Code ]

2916399090
Hazard InformationBack Directory
[Uses]

5-Chloro-m-salicylic Acid was studied as a potential selective lactate receptor (GPR81) agonists with antilipolytic effects.
[Uses]

GPR81, 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 Activity]

3-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 vitro]

in 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 vivo]

in 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].
[storage]

Store at RT
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

3-CHLORO-5-HYDROXY-BENZOIC ACID(53984-36-4)1HNMR
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