17359-54-5

Basic information

• Product Name: 2,4-DIHYDROXY-1,4-BENZOXAZIN-3-ONE
• Synonyms: 2,4-DIHYDROXY-1,4-BENZOXAZINONE;2H-1,4-Benzoxazin-3(4H)-one,2,4-dihydroxy-
• CAS NO: 17359-54-5
• Molecular Formula: C₈H₇NO₄
• Molecular Weight: 181.15
• Mol File: 17359-54-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 157-159℃
• Boiling Point: 405.1 °C at 760 mmHg
• Flash Point: 198.8 °C
• Appearance: /
• Density: 1.664 g/cm³
• Vapor Pressure: 2.74E-07mmHg at 25°C
• Refractive Index: 1.704
• PKA: 7.72±0.40(Predicted)
• CAS DataBase Reference: 2,4-DIHYDROXY-1,4-BENZOXAZIN-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIHYDROXY-1,4-BENZOXAZIN-3-ONE(17359-54-5)
• EPA Substance Registry System: 2,4-DIHYDROXY-1,4-BENZOXAZIN-3-ONE(17359-54-5)

Safety Data

• Hazardous Substances Data: 17359-54-5(Hazardous Substances Data)

Usage

Description

2,4-DIHYDROXY-1,4-BENZOXAZIN-3-ONE, also known as DIBOA, is a lactol belonging to the benzoxazine family. It is characterized by the presence of two hydroxy substituents at positions 2 and 4, as well as a keto group at position 3. DIBOA is an allelopathic biochemical produced by grasses and has been found to exhibit health-promoting effects in rats.

Uses

Used in Health Promotion:
2,4-DIHYDROXY-1,4-BENZOXAZIN-3-ONE is used as a health-promoting agent in rats, where it has been observed to have beneficial effects on their overall health and well-being.
Used in Allelopathic Applications:
In the field of allelopathy, 2,4-DIHYDROXY-1,4-BENZOXAZIN-3-ONE is used as a biochemical produced by grasses. It plays a crucial role in the interactions between plants, potentially influencing the growth and development of neighboring plant species.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx.

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

Upstream product

• 23520-34-5 Blepharigenin 
• 100675-97-6 2-Bromo-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one 
• 55574-10-2 4-Hydroxy-2-methoxy-2H-1,4-benzoxazin-3(4H)-one 
• 157067-48-6 2,2-Di-tert-butyl-1,3,4,5-tetraoxa-9b-aza-2-sila-cyclopenta[a]cyclopropa[b]naphthalene 
• 89898-78-2 4-hydroxy-2,3-dioxo-1,4-benzoxazine 
• 1026342-24-4 Methoxymethoxy-(2-nitro-phenoxy)-acetic acid isopropyl ester 
• 37682-31-8 ethyl o-nitrophenoxyacetate 
• 157067-46-4 4-hydroxy-2H-1,4-benzoxazin-3(4H)-one 
• 771-26-6 4-hydroxy-2H-1,4-benzoxazin-3-one 
• 824-38-4 potassium 2-nitrophenoxide 
• 55544-85-9 methyl α-(2-nitrophenoxy)-α-methoxyacetate 
• 14676-36-9 2-hydroxy-α,α-dichloroacetanilide 
• 95-55-6 2-amino-phenol 

Downstream Products

• 122978-13-6 N-[2,2,2-Trichloro-1-(2-hydroxy-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yloxy)-ethyl]-benzamide 
• 59-49-4 2-Benzoxazolinone 
• 23520-34-5 Blepharigenin 
• 188358-89-6 2-benzyloxy-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one 
• 188358-91-0 2-benzyloxy-4-methoxy-2H-1,4-benzoxazin-3(4H)-one 
• 142729-01-9 2-Hydroxy-7-phenylsulfanyl-4H-benzo[1,4]oxazin-3-one 
• 142728-97-0 2-Hydroxy-6-(4-hydroxy-phenyl)-4H-benzo[1,4]oxazin-3-one 
• 142729-00-8 2-Hydroxy-6-phenylsulfanyl-4H-benzo[1,4]oxazin-3-one 
• 142729-02-0 2-Hydroxy-8-phenylsulfanyl-4H-benzo[1,4]oxazin-3-one 
• 142728-98-1 2-Hydroxy-6-(2-hydroxy-5-methyl-phenyl)-4H-benzo[1,4]oxazin-3-one 
• 142728-99-2 2-Hydroxy-6-(1-methyl-4-oxo-cyclohexa-2,5-dienyl)-4H-benzo[1,4]oxazin-3-one 
• 142728-96-9 4-(4-Dimethylamino-phenyl)-2-hydroxy-4H-benzo[1,4]oxazin-3-one 

Relevant articles and documents

Biotransformation of ethyl 2-(2′-nitrophenoxy)acetate to benzohydroxamic acid (D-DIBOA) by Escherichia coli

Benzohydroxamic acids, such as DIBOA, exhibit interesting biological properties (herbicidal, fungicidal and bactericidal). Recently, the synthesis of DIBOA has been simplified to only two steps. This paper explores the possibility of replacing the second stage in the chemical synthesis of D-DIBOA by a biotransformation using a strain of Escherichia coli and a strain of Serratia marcescens. Biotransformation experiments were carried out for both strains in the presence of different concentrations (0.25, 0.5 and 1 mg/mL) of the precursor (ethyl 2-(2′-nitrophenoxy)acetate) under aerobic and anaerobic conditions. Both strains tolerated the concentrations of precursor investigated here. Higher biotransformation yields were reached for E. coli under aerobic conditions. The UV/vis spectra and 1H/13C spectroscopic data obtained from HPLC-DAD and NMR, respectively, for the compounds obtained in the biotransformation reaction confirmed the presence of D-DIBOA in cultures of E. coli. The maximum yields were obtained in experiments supplemented with 0.5 mg/mL of precursor and these were 20.14 ± 1.87% under aerobic conditions and 8.17 ± 0.94% under anaerobic conditions.

Occurrence and characterization of 2-hydroxy-1,4-benzoxazin-3-one and indole hydroxylases in juvenile wheat

Cyclic hydroxamic acids, 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA) and its 7-methoxy analogue (DIMBOA), occur transiently in high amounts in wheat and maize during the juvenile, non-autotrophic stage of growth. To elucidate the biosynthetic enzymes operating for the transient production of these compounds, we examined the hydroxylating activities for 2-hydroxy-1,4-benzoxazin-3-one (HBOA), the immediate precursor of DIBOA, and indole, the first intermediate of the biosynthetic pathway that branches off from the tryptophan pathway, by using microsomes prepared from wheat seedlings. Both hydroxylases occurred soon after germination, reached a maximum 48 h after germination, and decreased to finally disappear as the plants grew into the autotrophic growth stage. The mode of appearance and disappearance similar to that of hydroxamic acids, suggesting that elevated expression of the whole set of enzymes involved in the biosynthesis after indole was responsible for the transient occurrence of hydroxamic acids. The hydroxylating activity was also observed for 1,4-benzoxazin-3-one, a putative precursor of HBOA, but to significantly less extent than that for HBOA and indole.

α-Hydroxylation of Cyclic Hydroxamic Acids by Peroxide Oxidation: A Novel Approach to Allelochemicals from Graminae

Naturally occurring hemiacetals DIBOA and DIMBOA were synthesized by the first α-hydroxylation of N-hydroxylactams via m-chloroperbenzoic acid oxidation of corresponding cyclosilyl enol ethers.