3-CHLORO-5-HYDROXY-BENZOIC ACID
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3-CHLORO-5-HYDROXY-BENZOIC ACID
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CAS No:
53984-36-4
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Formula:
C7H5ClO3
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Chemical Name:
3-CHLORO-5-HYDROXY-BENZOIC ACID
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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
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CAS No:
Characteristics
57.5
1.8
white to beige
1.5±0.1 g/cm3
244.0 to 248.0 °C
364.8°C at 760 mmHg
174.4±23.7 °C
1.630
DMSO: soluble 15mg/mL (clear solution)
room temp
Safety Information
NONH for all modes of transport
3
22-37/38-41
26-36
Xn
P261-P280-P305 + P351 + P338
H302-H315-H318-H335
3-CHLORO-5-HYDROXY-BENZOIC ACID Use and Manufacturing
Alumina (1.65 g, 60 mmol) and iodine (21 g, 82 mmol) were refluxed in toluene (200 mL) for 2 hours. Alumina (1.65 g, 60 mmol) and iodine (21 g, 82 mmol) were refluxed in toluene (200 mL) for 2 hours. Then, 3-chloro-5-methoxybenzoic acid (11.2 g, 60.2 mmol; see step (i) above) dissolved in toluene (50 mL) was added, together with tetrabutylammonium iodide (1.5 g, 4 [MMOL), ] and the mixture was refluxed for another 2 hours. After cooling to ambient temperature, extractive work up gave 8.7 g, 50 mmol (yield: 83percent) of the sub-title compound. [APOS;H-NMR (300 MHZ] ; acetone-d6): [A 9.] 27 (s, [I H), ] 7.48 (m, [1H), ] 7.44 (m, [1H), ] 7. 11 (m, 1H)
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]
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