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Merck
CN

SMB01337

DIMBOA

Synonym(s):

(±)-DIMBOA, 2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3(4H)-one, 2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one, 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, 2,4-Dihydroxy-7-methoxy-2H-benzo[b][1,4]oxazin-3(4H)-one, 2,4-dihydroxy-7-methoxy- (6CI, 7CI, 8CI, 9CI, ACI), 2H-1,4-Benzoxazin-3(4H)-one

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About This Item

Empirical Formula (Hill Notation):
C9H9NO5
Molecular Weight:
211.17
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD01663964

Key Documents

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SMILES string

N1(c2c(cccc2)OC(C1=O)O)O

InChI

1S/C8H7NO4/c10-7-8(11)13-6-4-2-1-3-5(6)9(7)12/h1-4,8,11-12H

InChI key

COVOPZQGJGUPEY-UHFFFAOYSA-N

assay

≥92% (HPLC)

form

solid

mp

150—155 °C

storage temp.

2-8°C

Quality Level

100

Application

Metabolomics research

General description

DIMBOA is a powerful antibiotic present in maize and wheat. It was first identified in maize in 1962 as a saccharin-like ″sweet substance in corn″. DIMBOA is stored as an inactive precursor, DIMBOA-glucoside, which is activated by glucosidases in response to insect feeding. In maize, DIMBOA functions as natural defense against damaging insect pests and pathogens, including fungi and bacteria. DIMBOA level varies among individual plants, higher concentrations are typically found in young seedlings and lower concentrations in adult maize plants.

Other Notes

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Storage Class

11 - Combustible Solids

wgk

WGK 3

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000507601
0000507601
0000497206
0000497206
0000482803

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Cuiping Zhang et al.
The New phytologist, 229(4), 2273-2287 (2020-10-01)
2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) and DIMBOA-glucoside (DIMBOA-Glc) are anti-insect benzoxazinoids in maize, yet very little information is known about how they are regulated. Reverse genetics, kinase activity analysis, phytohormone and DIMBOA/DIMBOA-Glc quantification, bioassays and transcriptome analysis were employed to study the function
A M Giuffrida Stella et al.
Gerontology, 33(3-4), 136-148 (1987-01-01)
During aging there are several structural, functional and biochemical alterations, including changes in macromolecular composition and turnover. Regulation of gene expression, DNA and RNA synthesis, total poly(A)+ and poly(A)- RNA contents, qualitative and quantitative changes of synaptosomal plasma membrane proteins
Karina Lucas Silva-Brandão et al.
Pest management science, 77(1), 518-526 (2020-08-21)
2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), the main benzoxazinoid found in corn, elicits variable larval responses from different pest moths. For the widespread and highly polyphagous Spodoptera frugiperda (Lepidoptera: Noctuidae), the fall-armyworm (FAW), DIMBOA acts as a feeding stimulant and improves larval growth at

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