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DIMBOA

CAT: 0804-HY-N7432-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-N7432-02Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
DIMBOA, an antibiotic, has antibacterial properties and inhibits bacteria such as Staphylococcus aureus and the mycotoxin-producing fungus Fusarium graminearum (which causes scab) . DIMBOA exhibits strong free radical scavenging activity and weak iron (III) ion reducing activity, and has antioxidant activity. DIMBOA inhibits the biosynthesis and accumulation of toxic trichothecenes by affecting the expression of Tri6 and Tri5. DIMBOA reduces plant susceptibility to scab. DIMBOA also exhibits cytotoxicity to plant cells, causing plasmolysis, cell collapse, and cell rupture[1][2][3][4][5].
CAS Number
15893-52-4
UNSPSC
12352005
Hazard Statement
H315, H319, H320
Target
Antibiotic; Bacterial; Fungal
Type
Natural Products
Related Pathways
Anti-infection
Applications
COVID-19-immunoregulation
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/dimboa.html
Concentration
10mM
Purity
99.81
Solubility
DMSO : 50 mg/mL (ultrasonic)
Smiles
O=C1C(O)OC2=CC(OC)=CC=C2N1O
Molecular Formula
C9H9NO5
Molecular Weight
211.17
Precautions
H315, H319, H320
References & Citations
[1]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) .|[2]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.|[3]Sasai H, et al. Species-specific glucosylation of DIMBOA in larvae of the rice Armyworm. Biosci Biotechnol Biochem. 2009;73 (6) :1333-1338.|[4]Etzerodt T, et al. 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3 (4H) -one (DIMBOA) inhibits trichothecene production by Fusarium graminearum through suppression of Tri6 expression. Int J Food Microbiol. 2015 Dec 2;214:123-128.|[5]Sahi S V, et al. The corn wound metabolite DIMBOA causes cell death in tobacco and corn[J]. Plant Science, 1995, 108 (1) : 31-40.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one

DIMBOA is a lactol that is DIBOA in which the hydrogen at position 7 is replaced by a methoxy group. It has been isolated from the maize plants. It has a role as an allelochemical and a plant metabolite. It is a cyclic hydroxamic acid, an aromatic ether, a lactol and a benzoxazine. It is functionally related to a DIBOA.

CAS Number15893-52-4
PubChem CID2358
IUPAC Name2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one
Molecular FormulaC9H9NO5
Molecular Weight211.17
XLogP0
Topological Polar Surface Area79.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Heavy Atom Count15
Formal Charge0
Complexity259
SMILES
COC1=CC2=C(C=C1)N(C(=O)C(O2)O)O
InChI
InChI=1S/C9H9NO5/c1-14-5-2-3-6-7(4-5)15-9(12)8(11)10(6)13/h2-4,9,12-13H,1H3
InChIKey
GDNZNIJPBQATCZ-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one
CAS: 15893-52-4
CID: 2358
Formula: C9H9NO5
MW: 211.17
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight211.17
XLogP30
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Exact Mass211.04807239
Monoisotopic Mass211.04807239
Topological Polar Surface Area79.2 Ų
Heavy Atom Count15
Formal Charge0
Complexity259
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
BA1037-100DIMBOA
A22058-10DIMBOA 10mg
A22058-1DIMBOA 1mg
A22058-50DIMBOA 50mg
TRC-D459953-0.5MGDIMBOA-Glc
A22058-25DIMBOA 25mg
A22058-100DIMBOA 100mg
A22058-5DIMBOA 5mg

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