7-HYDROXY-2-OXO-2H-CHROMENE-3-CARBONITRILE

Names

[ CAS No. ]:
19088-73-4

[ Name ]:
7-HYDROXY-2-OXO-2H-CHROMENE-3-CARBONITRILE

[Synonym ]:
3-Cyano-7-hydroxycoumarin
7-hydroxy-2-oxochromene-3-carbonitrile
7-Hydroxy-2-oxo-2H-chromene-3-carbonitrile

Biological Activity

[Description]:

3-Cyanoumbelliferone is a coumarin derivative, acting as molecular probe and fluorescent dye. 3-Cyanoumbelliferone is also a macrophage migration inhibitory factor (MIF) tautomerase inhibitor with a Ki of 2.9 μM[1].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[Target]

Ki: 2.9 μM (MIF)[1]

[References]

[1]. Orita M, et al. Coumarin and chromen-4-one analogues as tautomerase inhibitors of macrophage migration inhibitory factor: discovery and X-ray crystallography. J Med Chem. 2001 Feb 15;44(4):540-7.

Chemical & Physical Properties

[ Density]:
1.5 g/cm3

[ Boiling Point ]:
436.6ºC at 760 mmHg

[ Melting Point ]:
≥250ºC(lit.)

[ Molecular Formula ]:
C₁₀H₅NO₃

[ Molecular Weight ]:
187.15200

[ Flash Point ]:
217.8ºC

[ Exact Mass ]:
187.02700

[ PSA ]:
74.23000

[ LogP ]:
1.37028

[ Vapour Pressure ]:
3.13E-08mmHg at 25°C

[ Index of Refraction ]:
1.667

[ Water Solubility ]:
DMF: soluble

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302 + H312 + H332-H315-H319-H335

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2932209090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932209090

[ Summary ]:
2932209090. other lactones. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Potent inhibition of CYP1A2 by Frutinone A, an active ingredient of the broad spectrum antimicrobial herbal extract from P. fruticosa.

Xenobiotica 42 , 989-1000, (2012)

1. Frutinone is an active ingredient extracted from the lipophilic fraction of the Polygala Fruticosa demonstrating various antibacterial and fungal properties. The aim of this study was to characteri...

A continuous fluorometric assay for cytochrome P-450-dependent mixed function oxidases using 3-cyano-7-ethoxycoumarin.

Anal. Biochem. 172 , 304, (1988)

A direct fluorometric procedure for the continuous determination of cytochrome P-450-dependent mixed function oxidases, using 3-cyano-7-ethoxycoumarin substrate, is described. The reaction product, 3-...

Assessment of cytochrome P450 fluorometric substrates with rainbow trout and killifish exposed to dexamethasone, pregnenolone-16alpha-carbonitrile, rifampicin, and beta-naphthoflavone.

Aquat. Toxicol. 97 , 324-333, (2010)

Cytochrome P450s (CYPs) are important xenobiotic metabolizing proteins. While their functions are well understood in mammals, CYP function in non-mammalian vertebrate systems is much less defined, wit...