Cinnabarinic acid

Modify Date: 2024-01-02 20:43:30

Cinnabarinic acid structure	Common Name	Cinnabarinic acid
	CAS Number	606-59-7	Molecular Weight	300.223
	Density	1.8±0.1 g/cm3	Boiling Point	536.8±50.0 °C at 760 mmHg
	Molecular Formula	C₁₄H₈N₂O₆	Melting Point	>300ºC
	MSDS	Chinese USA	Flash Point	278.4±30.1 °C

Use of Cinnabarinic acid

Cinnabarinic acid is a specific orthosteric agonist of mGlu4 by interacting with residues of the glutamate binding pocket of mGlu4, has no activity at other mGlu receptors. Cinnabarinic acid is an endogenous metabolite of the kynurenine pathway of tryptophan. Cinnabarinic acid induces cell apoptosis[1].

Name	Cinnabarinic Acid
Synonym	More Synonyms

Description	Cinnabarinic acid is a specific orthosteric agonist of mGlu4 by interacting with residues of the glutamate binding pocket of mGlu4, has no activity at other mGlu receptors. Cinnabarinic acid is an endogenous metabolite of the kynurenine pathway of tryptophan. Cinnabarinic acid induces cell apoptosis[1].
Related Catalog	Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Others Signaling Pathways >> GPCR/G Protein >> mGluR
Target	mGluR4
In Vitro	Cinnabarinic acid (0-100 μM) does not activate mGlu1, mGlu2, mGlu5, mGlu6, mGlu7, and mGlu8 receptors as shown by measurements of [3H]InsP formation. In contrast, cinnabarinic acid acts as a partial agonist of mGlu4 receptors by increasing [3H]InsP formation by approximately 35% at 100 μM, which is 5-fold less efficacious than ACPT-I in activating mGlu4 receptors in HEK293 cells transiently transfected with rat mGlu1, -2, -4, -5, -6, -7, or -8 receptors[1]. Cinnabarinic acid (0-100 μM) reduces cAMP formation in a concentration-dependent manner with an excellent potency and efficacy. At 30 μM, cinnabarinic acid is effective at 30 μM, and substantially inhibits cAMP formation in cultured cerebellar granule cells[1].
References	[1]. F Fazio, et al. Cinnabarinic acid, an endogenous metabolite of the kynurenine pathway, activates type 4 metabotropic glutamate receptors.Mol Pharmacol. 2012 May;81(5):643-56. [2]. Martina Ulivieri, et al. The Trace Kynurenine, Cinnabarinic Acid, Displays Potent Antipsychotic-Like Activity in Mice and Its Levels Are Reduced in the Prefrontal Cortex of Individuals Affected by Schizophrenia. Schizophr Bull. 2020 Jun 7;sbaa074. [3]. Francesco Fazio, et al. Cinnabarinic acid and xanthurenic acid: Two kynurenine metabolites that interact with metabotropic glutamate receptors. Neuropharmacology. 2017 Jan;112(Pt B):365-372.

Density	1.8±0.1 g/cm3
Boiling Point	536.8±50.0 °C at 760 mmHg
Melting Point	>300ºC
Molecular Formula	C₁₄H₈N₂O₆
Molecular Weight	300.223
Flash Point	278.4±30.1 °C
Exact Mass	300.038239
PSA	143.72000
LogP	-0.13
Vapour Pressure	0.0±1.5 mmHg at 25°C
Index of Refraction	1.780

Cinnabarinic acid MSDS(Chinese)

RIDADR	NONH for all modes of transport

3-Benzyloxy-4-m...

CAS#:50425-08-6

Cinnabarinic acid

CAS#:606-59-7

Literature: Korshunova, Z. I.; Popova, E. B.; Glibin, E. N.; Ginzburg, O. F. Journal of Organic Chemistry USSR (English Translation), 1991 , vol. 27, # 2.2 p. 314 - 319 Zhurnal Organicheskoi Khimii, 1991 , vol. 27, # 2 p. 369 - 376

N/A

CAS#:137152-34-2

Cinnabarinic acid

CAS#:606-59-7

9-(3-dimethylam...

CAS#:137179-11-4

N/A

CAS#:137179-13-6

3-Hydroxyanthra...

CAS#:548-93-6

Cinnabarinic acid

CAS#:606-59-7

6-amino-3-[(2-c...

CAS#:112817-49-9

Literature: Manthey, Michael K.; Pyne, Stephen G.; Truscott, Roger J. W. Journal of Organic Chemistry, 1988 , vol. 53, # 7 p. 1486 - 1488

3-Hydroxy-2-nit...

CAS#:602-00-6

N-(3-dimethylam...

CAS#:83748-53-2

Cinnabarinic acid

CAS#:606-59-7

N/A

CAS#:137152-36-4

Detail

3-Hydroxy-4-met...

CAS#:71489-74-2

N-(3-dimethylam...

CAS#:83748-53-2

Cinnabarinic acid

CAS#:606-59-7

N/A

CAS#:137152-37-5

Detail

3-Hydroxy-2-nit...

CAS#:602-00-6

Cinnabarinic acid

CAS#:606-59-7

Literature: Butenandt et al. Justus Liebigs Annalen der Chemie, 1957 , vol. 602, p. 72,79

3-Hydroxyanthra...

CAS#:548-93-6

N/A

CAS#:96464-02-7

Cinnabarinic acid

CAS#:606-59-7

6-amino-3-[(2-c...

CAS#:112817-49-9

Detail

Literature: Hick, Larry A.; Manthey, Michael K.; Truscott, Roger J. W. Journal of Heterocyclic Chemistry, 1991 , vol. 28, # 4 p. 1157 - 1160

3-Hydroxyanthra...

CAS#:548-93-6

~38%

Cinnabarinic acid

CAS#:606-59-7

Literature: Pasceri, Raffaele; Siegel, David; Ross, David; Moody, Christopher J. Journal of Medicinal Chemistry, 2013 , vol. 56, # 8 p. 3310 - 3317

3-Hydroxy-2-nit...

CAS#:602-00-6

N/A

CAS#:137152-34-2

Cinnabarinic acid

CAS#:606-59-7

9-(3-dimethylam...

CAS#:137179-11-4

Detail

Precursor 4
CAS#:548-93-6 3-Hydroxyanthra... CAS#:602-00-6 3-Hydroxy-2-nit... CAS#:83748-53-2 N-(3-dimethylam... CAS#:71489-74-2 3-Hydroxy-4-met...
DownStream 1
CAS#:548-93-6 3-Hydroxyanthra...

Aminophenoxazinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis of exfoliazone and chandrananimycin A.

J. Med. Chem. 56(8) , 3310-7, (2013)

A range of 2-aminophenoxazin-3-ones has been prepared by oxidative cyclocondensation of 2-aminophenols, including the natural products exfoliazone and chandrananimycin A, both synthesized for the firs...

Simultaneous determination of 3-hydroxyanthranilic and cinnabarinic acid by high-performance liquid chromatography with photometric or electrochemical detection.

Anal. Biochem. 200(2) , 273-9, (1992)

A convenient and rapid method for the simultaneous determination by HPLC of 3-hydroxyanthranilic acid and the dimer derived by its oxidation, cinnabarinic acid, is described. Buffers or biological sam...

Oxidation of 3-hydroxyanthranilic acid to the phenoxazinone cinnabarinic acid by peroxyl radicals and by compound I of peroxidases or catalase.

Biochemistry 31(34) , 8090-7, (1992)

Since 3-hydroxyanthranilic acid (3HAA), an oxidation product of tryptophan metabolism, is a powerful radical scavenger [Christen, S., Peterhans, E., & Stocker, R. (1990) Proc. Natl. Acad. Sci. U.S.A. ...

2-amino-3-oxophenoxazine-1,9-dicarboxylic acid

2-Amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid

3H-Phenoxazine-1,9-dicarboxylic acid, 2-amino-3-oxo-