Xanthopterin

Names

[ CAS No. ]:
119-44-8

[ Name ]:
Xanthopterin

[Synonym ]:
2-aminopteridine-4(3H),6(5H)-dione
4,6-Pteridinedione,2-amino-1,5-dihydro-(9CI)
4,6-pteridinediol, 2-amino-
Xanthopterin
2-amino-3,5-dihydro-pteridine-4,6-dione
2-amino-1,5-dihydropteridine-4,6-quinone
Uropterin
2-amino-3,5-dihydropteridine-4,6-dione
4,6-Pteridinedione, 2-amino-1,5-dihydro-
6(2H)-Pteridinone, 1,5-dihydro-4-hydroxy-2-imino-
2-AMINO-1,5-DIHYDROPTERIDINE-4,6-DIONE
4-Hydroxy-2-imino-1,5-dihydro-6(2H)-pteridinone
EINECS 204-325-0
2-Amino-3,5-dihydro-pteridin-4,6-dion
4(1H)-pteridinone, 2,3-dihydro-6-hydroxy-2-imino-
2-Amino-1,5-dihydro-4,6-pteridinedione
6-Hydroxy-2-imino-2,3-dihydropteridin-4(1H)-one
2-Amino-4-oxo-6-hydroxy-3,4-dihydropteridine
2-Aminopteridine-4,6-diol
2-azanyl-1,5-dihydropteridine-4,6-dione
2-AMINO-4,6-DIHYDROXYPTERIDENE
2-Amino-4,6(1H,5H)-pteridinedione
MFCD00151242
xanthopterine

Biological Activity

[Description]:

Xanthopterin, an unconjugated pteridine compound, is the main component of the yellow granule in the Oriental hornet bear wings, produces a characteristic excitation/emission maximum at 386/456 nm[2]. Xanthopterin (XPT) causes renal growth and hypertrophy in rat[1].Xanthopterin inhibits RNA synthesis[4].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

[In Vitro]

Xanthopterin (7.8-250 mM; 24 hours) show a significant reduction in mitochondrial activity with respect to controls (IC50=109 mM)[2]. Cell Viability Assay[2] Cell Line: MCF-7 cells Concentration: 7.8 mM-250 mM Incubation Time: 24 hours Result: Resulted in reduction in mitochondrial activity.

[References]

[1]. Xanthopterin (XPT), an unconjugated pteridine compound, affects cell growth and differentiation. When injected into rats, XPT has caused changes that have been interpreted as renal growth and hypertrophy.

[2]. Lord JL, et al. Cytotoxicity of xanthopterin and isoxanthopterin in MCF-7 cells. Cancer Lett. 2005 May 10;222(1):119-24.

[3]. Plotkin M, et al. Xanthopterin in the Oriental hornet (Vespa orientalis): light absorbance is increased with maturation of yellow pigment granules. Photochem Photobiol. 2009 Jul-Aug;85(4):955-61.

[4]. Ziegler I, et al. Pterins and the regulation of lymphocyte activation on the mode of xanthopterin action. Hoppe Seylers Z Physiol Chem. 1984 Jun;365(6):667-73.

Chemical & Physical Properties

[ Density]:
2.2±0.1 g/cm3

[ Boiling Point ]:
686.5ºC at 760mmHg

[ Melting Point ]:
410ºC

[ Molecular Formula ]:
C₆H₅N₅O₂

[ Molecular Weight ]:
179.136

[ Flash Point ]:
369ºC

[ Exact Mass ]:
179.044327

[ PSA ]:
117.52000

[ LogP ]:
-3.90

[ Index of Refraction ]:
1.992

[ Storage condition ]:
2-8°C

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-37/39

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%