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

• CAS: 17359-54-5
• Catalog Number: ACM17359545
• Category: Main Products
• Molecular Weight: 0
• Molecular Formula: C₈H₇NO₄
• Synonyms: 2,4-DIHYDROXY-1,4-BENZOXAZINONE
• IUPAC Name: 2,4-dihydroxy-1,4-benzoxazin-3-one
• Canonical SMILES: C1=CC=C2C(=C1)N(C(=O)C(O2)O)O
• InChI Key: COVOPZQGJGUPEY-UHFFFAOYSA-N
• Boiling Point: 405.1ºC at 760mmHg
• Melting Point: 157-159°C
• Flash Point: 198.8ºC
• Density: 1.664g/cm³
• Exact Mass: 181.03800
• H-Bond Acceptor: 4
• H-Bond Donor: 2

Case Study

Plant Functions of Benzoxazinoids Such as 2,4-Dihydroxy-1,4-Benzoxazin-3-One

De Bruijn, et al. Phytochemistry, 2018, 155, 233-243.

Benzoxazinoids demonstrate well-established allelopathic functionality which stands as one of their primary functions. Roots and root exudates of young maize, wheat, and rye exhibit high benzoxazinoid levels to aid in competition against other plants during their early growth stages. Hydroxamic acids like 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA) and DIMBOA demonstrate stronger allelopathic and phytotoxic activity compared to lactams such as HBOA and HMBOA. Benzoxazolinones BOA and MBOA display allelopathic potency that falls between the levels observed in hydroxamic acids and lactams.
Natural benzoxazinoids DIBOA and DIBOA-Glc show the strongest allelopathic effects with substantial root length inhibition at concentrations ranging from 10^-3 to 10^-4 M based on species sensitivity. The activity of DIBOA remains unchanged after glycosylation. Studies demonstrated the ability to increase both selectivity and potency of phytotoxic effects through chemical modification of 4-hydroxy-1,4-benzoxazin 3-one.
Studies have demonstrated that the 1,4-benzoxazin-3-one skeleton serves as a viable framework for developing new antibacterial substances. The natural benzoxazinone monomers show limited antimicrobial activity but chemical changes to the 1,4-benzoxazin-3-one framework create effective antimicrobial substances.

Effects of Benzoxazinoids Such as 2,4-Dihydroxy-1,4-Benzoxazin-3-One on the Growth of Cress Seedlings

Kato-Noguchi, Hisashi, et al. Journal of plant physiology, 2010, 167(15), 1221-1225.

This research examined how three benzoxazinone groups together with their degradation products affect root development and α-amylase activity in cress seedlings by studying distinct high-activity (DIMBOA, DIBOA, D-DIMBOA, D-DIBOA), medium-activity (D-HMBOA, D-HBOA, MBOA, BOA, APO) and low-activity (HBOA, HMBOA, AHPO, AMPO) compounds.
The study of structure-activity relationships demonstrates that compounds with a benzoxazinone framework show maximum activity. The presence of a hydroxyl group at the N-4 position of benzoxazinone is crucial for inhibitory activity but the hydroxyl group at the C-2 position shows no significant effect.
Analysis of concentration-response curves and I50 values demonstrated that root development and α-amylase activity in seedlings move in tandem. The enzyme α-Amylase plays a crucial role in seed germination and supports early seedling growth until photosynthesis starts producing adequate energy. The results suggest that the compounds being studied inhibit root development in cress seedlings through α-amylase activity disruption.

Custom Q&A

What is the molecular formula of 2,4-Dihydroxy-1,4-benzoxazin-3-one?

The molecular formula of 2,4-Dihydroxy-1,4-benzoxazin-3-one is C8H7NO4.

What is the molecular weight of 2,4-Dihydroxy-1,4-benzoxazin-3-one?

The molecular weight of 2,4-Dihydroxy-1,4-benzoxazin-3-one is 181.15 g/mol.

What are the synonyms for 2,4-Dihydroxy-1,4-benzoxazin-3-one?

The synonyms for 2,4-Dihydroxy-1,4-benzoxazin-3-one are DIBOA, 17359-54-5, 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one, and 2,4-Dihydroxy-1,4-benzoxazinone.

What is the structure of 2,4-Dihydroxy-1,4-benzoxazin-3-one?

The structure of 2,4-Dihydroxy-1,4-benzoxazin-3-one can be viewed at https://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?cid=28495&t=l.

What is the IUPAC name of 2,4-Dihydroxy-1,4-benzoxazin-3-one?

The IUPAC name of 2,4-Dihydroxy-1,4-benzoxazin-3-one is 2,4-dihydroxy-1,4-benzoxazin-3-one.

What is the InChI of 2,4-Dihydroxy-1,4-benzoxazin-3-one?

The InChI of 2,4-Dihydroxy-1,4-benzoxazin-3-one is InChI=1S/C8H7NO4/c10-7-8(11)13-6-4-2-1-3-5(6)9(7)12/h1-4,8,11-12H.

What is the InChIKey of 2,4-Dihydroxy-1,4-benzoxazin-3-one?

The InChIKey of 2,4-Dihydroxy-1,4-benzoxazin-3-one is COVOPZQGJGUPEY-UHFFFAOYSA-N.

What is the CAS number of 2,4-Dihydroxy-1,4-benzoxazin-3-one?

The CAS number of 2,4-Dihydroxy-1,4-benzoxazin-3-one is 17359-54-5.

How many hydrogen bond donor counts does 2,4-Dihydroxy-1,4-benzoxazin-3-one have?

2,4-Dihydroxy-1,4-benzoxazin-3-one has 2 hydrogen bond donor counts.

How many hydrogen bond acceptor counts does 2,4-Dihydroxy-1,4-benzoxazin-3-one have?

2,4-Dihydroxy-1,4-benzoxazin-3-one has 4 hydrogen bond acceptor counts.