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dimboa

Names

[ CAS No. ]:
15893-52-4

[ Name ]:
dimboa

[Synonym ]:
2,4-dihydroxy-7-methoxybenzoxazin-3-one
2,4-Dihydroxy-7-methoxy-1,4-benzoxazinone
2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one
2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one
2H-1,4-BENZOXAZIN-3(4H)-ONE,2,4-DIHYDROXY-7-METHOXY
2,4-Dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one

Biological Activity

[Description]:

DIMBOA, an antibiotic, is a benzoxazinoid, part of the chemical defense system of graminaceous plants such as maize, wheat, and rye. DIMBOA possess growth inhibitory properties against many strains of studied bacteria and fungi, such as Staphylococcus aureus, Escherichia coli as well as against Saccharomyces cerevisiae. DIMBOA exhibits a potent free-radical scavenging activity and a weaker iron (III) ions reducing activity. Antioxidant activity[1][2].

[Related Catalog]:

Research Areas >> Infection
Signaling Pathways >> Anti-infection >> Fungal
Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Gleńsk M, et al. In vitro evaluation of the antioxidant and antimicrobial activity of DIMBOA [2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one]. Nat Prod Res. 2016;30(11):1305-1308.

[2]. Sasai H, et al. Species-specific glucosylation of DIMBOA in larvae of the rice Armyworm. Biosci Biotechnol Biochem. 2009;73(6):1333-1338.

[3]. Phuong, T.T.T., Yamamoto, M., Fujii, T. et al. Comparison of the ability to catabolize DIMBOA, a maize antibiotic, between Ostrinia furnacalis and Ostrinia scapulalis(Lepidoptera: Crambidae), with reference to their hybrids. Appl Entomol Zool 51, 143–149 (2016).

Chemical & Physical Properties

[ Density]:
1.589g/cm3

[ Boiling Point ]:
461.3ºC at 760mmHg

[ Melting Point ]:
150-155 °C

[ Molecular Formula ]:
C9H9NO5

[ Molecular Weight ]:
211.17100

[ Flash Point ]:
232.8ºC

[ Exact Mass ]:
211.04800

[ PSA ]:
79.23000

[ LogP ]:
0.19320

[ Vapour Pressure ]:
2.64E-09mmHg at 25°C

[ Index of Refraction ]:
1.658

[ Storage condition ]:
-20°C

Safety Information

[ Hazard Codes ]:
Xn

Related Compounds