DIMBOA | CAS#15893-52-4 | antibiotic present in maize, wheat, and related grasses

MedKoo Cat#: 555930 | Name: DIMBOA

Description:

WARNING: This product is for research use only, not for human or veterinary use.

DIMBOA is a powerful antibiotic present in maize, wheat, and related grasses, DIMBOA was first identified in maize in 1962 as the "corn sweet substance". Etiolated maize seedlings have a very sweet, almost saccharin-like taste due to their high DIMBOA content. DIMBOA is stored as an inactive precursor, DIMBOA-glucoside, which is activated by glucosidases in response to insect feeding.

Chemical Structure

DIMBOA

CAS#15893-52-4

Theoretical Analysis

MedKoo Cat#: 555930

Name: DIMBOA

CAS#: 15893-52-4

Chemical Formula: C9H9NO5

Exact Mass: 211.0481

Molecular Weight: 211.17

Elemental Analysis: C, 51.19; H, 4.30; N, 6.63; O, 37.88

Price and Availability

Size	Price	Availability
50mg	USD 750.00	2 Weeks
100mg	USD 1,250.00	2 Weeks
200mg	USD 1,950.00	2 Weeks
500mg	USD 2,950.00	2 Weeks
1g	USD 3,950.00	2 Weeks

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Related CAS #

15893-52-4

Synonym

DIMBOA; (±)-DIMBOA;

IUPAC/Chemical Name

2,4-dihydroxy-7-methoxy-2H-benzo[b][1,4]oxazin-3(4H)-one

InChi Key

GDNZNIJPBQATCZ-UHFFFAOYSA-N

InChi Code

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

SMILES Code

O=C1C(O)OC2=CC(OC)=CC=C2N1O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

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.

In vitro activity:

It was found that DIMBOA exhibits a potent free-radical scavenging activity and a weaker iron (III) ions reducing activity. Antimicrobial activity against selected G(+), G(-) bacterial strains and against yeasts-like reference strains of fungi was investigated using disk-diffusion method. It has been shown that 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. Reference: Nat Prod Res. 2016 Jun;30(11):1305-8. https://pubmed.ncbi.nlm.nih.gov/26166773/

In vivo activity:

When Bombyx mori larvae were fed artificial diets containing DIMBOA, they died in three days. Reference: Biosci Biotechnol Biochem. 2009 Jun;73(6):1333-8. https://pubmed.ncbi.nlm.nih.gov/19502734/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	50.0	236.77

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 211.17 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Gleńsk M, Gajda B, Franiczek R, Krzyżanowska B, Biskup I, Włodarczyk M. 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 Jun;30(11):1305-8. doi: 10.1080/14786419.2015.1054284. Epub 2015 Jul 13. PMID: 26166773. 2. Sasai H, Ishida M, Murakami K, Tadokoro N, Ishihara A, Nishida R, Mori N. Species-specific glucosylation of DIMBOA in larvae of the rice Armyworm. Biosci Biotechnol Biochem. 2009 Jun;73(6):1333-8. doi: 10.1271/bbb.80903. Epub 2009 Jun 7. PMID: 19502734.

In vitro protocol:

In vivo protocol:

1. Sasai H, Ishida M, Murakami K, Tadokoro N, Ishihara A, Nishida R, Mori N. Species-specific glucosylation of DIMBOA in larvae of the rice Armyworm. Biosci Biotechnol Biochem. 2009 Jun;73(6):1333-8. doi: 10.1271/bbb.80903. Epub 2009 Jun 7. PMID: 19502734.

1: Niu Y, Zhao X, Chao W, Lu P, Bai X, Mao T. Genetic Variation, DIMBOA Accumulation, and Candidate Gene Identification in Maize Multiple Insect- Resistance. Int J Mol Sci. 2023 Jan 21;24(3):2138. doi: 10.3390/ijms24032138. PMID: 36768464; PMCID: PMC9916695. 2: Förster C, Gershenzon J, Köllner TG. Evolution of DIMBOA-Glc O-Methyltransferases from Flavonoid O-Methyltransferases in the Grasses. Molecules. 2022 Feb 2;27(3):1007. doi: 10.3390/molecules27031007. PMID: 35164272; PMCID: PMC8839659. 3: Yang X, Hafeez M, Chen HY, Li WT, Ren RJ, Luo YS, Abdellah YAY, Wang RL. DIMBOA-induced gene expression, activity profiles of detoxification enzymes, multi-resistance mechanisms, and increased resistance to indoxacarb in tobacco cutworm, Spodoptera litura (Fabricius). Ecotoxicol Environ Saf. 2023 Nov 15;267:115669. doi: 10.1016/j.ecoenv.2023.115669. Epub 2023 Nov 8. PMID: 37944464. 4: Li X, Shi S, Zhang X, Li C, Wang H, Kang W, Yin G. Potential Effect of DIMBOA (2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one) on Alleviating the Autotoxic Coumarin Stress in Alfalfa (Medicago sativa) Seedlings. Life (Basel). 2022 Dec 19;12(12):2140. doi: 10.3390/life12122140. PMID: 36556505; PMCID: PMC9783211. 5: Israni B, Luck K, Römhild SCW, Raguschke B, Wielsch N, Hupfer Y, Reichelt M, Svatoš A, Gershenzon J, Vassão DG. Alternative transcript splicing regulates UDP-glucosyltransferase-catalyzed detoxification of DIMBOA in the fall armyworm (Spodoptera frugiperda). Sci Rep. 2022 Jun 20;12(1):10343. doi: 10.1038/s41598-022-14551-w. Erratum in: Sci Rep. 2022 Aug 2;12(1):13251. doi: 10.1038/s41598-022-17499-z. PMID: 35725775; PMCID: PMC9209448. 6: Zhang C, Li J, Li S, Ma C, Liu H, Wang L, Qi J, Wu J. ZmMPK6 and ethylene signalling negatively regulate the accumulation of anti-insect metabolites DIMBOA and DIMBOA-Glc in maize inbred line A188. New Phytol. 2021 Feb;229(4):2273-2287. doi: 10.1111/nph.16974. Epub 2020 Oct 27. PMID: 32996127. 7: Huang J, Bao M, Li J, Chen H, Xu D, Chen Z, Wen Y. Enantioselective Response of Wheat Seedlings to Imazethapyr: From the Perspective of Fe and the Secondary Metabolite DIMBOA. J Agric Food Chem. 2022 May 11;70(18):5516-5525. doi: 10.1021/acs.jafc.1c07727. Epub 2022 Apr 27. PMID: 35476430. 8: Silva-Brandão KL, Murad NF, Peruchi A, Martins CHZ, Omoto C, Figueira A, Brandão MM, Trigo JR. Transcriptome differential co-expression reveals distinct molecular response of fall-armyworm strains to DIMBOA. Pest Manag Sci. 2021 Jan;77(1):518-526. doi: 10.1002/ps.6051. Epub 2020 Sep 1. PMID: 32815313. 9: Butrón A, Chen YC, Rottinghaus GE, McMullen MD. Genetic variation at bx1 controls DIMBOA content in maize. Theor Appl Genet. 2010 Feb;120(4):721-34. doi: 10.1007/s00122-009-1192-1. Epub 2009 Nov 13. PMID: 19911162. 10: Huang J, Li J, Chen H, Shen C, Wen Y. Phytotoxicity alleviation of imazethapyr to non-target plant wheat: active regulation between auxin and DIMBOA. Environ Sci Pollut Res Int. 2023 Nov;30(54):116004-116017. doi: 10.1007/s11356-023-30608-3. Epub 2023 Oct 28. PMID: 37897577.