147802-14-0

Basic information

• Product Name: 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one
• CAS NO: 147802-14-0
• Molecular Weight: 181.148
• Mol File: 147802-14-0.mol

Chemical Properties

• CAS DataBase Reference: 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one(147802-14-0)
• EPA Substance Registry System: 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one(147802-14-0)

Safety Data

• Hazardous Substances Data: 147802-14-0(Hazardous Substances Data)

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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.

Novel compounds for use in weight loss and appetite suppression in humans

Phenolic compounds with a phenolic molecule to which are covalently linked an oxygen-containing group, a nitrogen or another oxygen containing group, and a C1-C4 alkoxy group, obtainable from monocotyledonous plants, or by chemical synthesis, have been found to act as weight loss agents, appetite suppressants, mood enhancers and adjunctive therapy for arthritis, sleep apnea, fibromyalgia, diabetes and hyperglycemia. Additional chemical compounds of the present invention may include benzoxazinoids-cyclic hydroxyamic acids, lactams, and corresponding glucosides, which may serve as precursors to phenolic compounds. The phenolic compounds and precursors of phenolic compounds of the present invention, at concentrations suitable for human therapeutic use, may be obtained from monocotyledonous plants such as corn in their early growth states which are timely harvested for optimum yield.

An improved synthesis of cyclic hydroxamic acids from Gramineae

The boron trichloride sensitive methoxymethyl (MOM) protecting group has been used to efficiently synthesize polymethoxylated derivatives of the benzoxazinone family of cyclic hydroxamic acids. The MOM group allows the unveiling of the hemiacetal at C-2 of these compounds without demethylating ring methoxy substituents, resulting in greatly increased yields.

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.

A new general approach to the 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one skeleton via diisobutylaluminum hydride reduction of 2,3-dioxo-1,4-benzoxazines

A series of naturally occurring hemiacetals 2a-d was synthesized by the chemoselective diisobutylaluminum hydride reduction of 2,3-dioxo-4H-1,4-benzoxazines 1a,b and their N-hydroxy derivatives 1c,d precursors. The procedure described represents a new general approach to the 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one skeleton giving rise to the bioactive natural hydroxamic acids 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one (2c) and 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (2d) in only three steps starting from nitrophenols.

Analogues of the Cyclic Hydroxamic Acid 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one: Decomposition to Benzoxazolinones and Reaction with β-Mercaptoethanol

Analogues of the aglucones of naturally occurring cyclic hydroxamic acids (2,4-dihydroxy-1,4-benzoxazin-3-ones) from Gramineae (Poaceae) have been synthesized by the reductive cyclization of the ring-substituted methyl α-(o-nitrophenoxy)-α-methoxyacetates, followed by demethylation of the C-2 methoxy group with BBr3 or BCl3 to reveal the 2-hydroxy group.A structure-activity series was produced by varying the substituent at C-7 on the aromatic ring .The pKa values for the hydroxamic acid and the phenol moieties were determined for each member of the C-7 series.They correlated well with ? in a linear free energy relationship (LFER) yielding values of ρ = 0.71 (with ?p) for pKa1 (the hydroxamic acid) and ρ = 1.6 (with ρm) for pKa2 (the phenol).A LFER also existed between the rate constants for the unimolecular decomposition of these hydroxamic acids to benzoxazolinones and ?+ (ρ = -1.1).The rates of hydroxamic acid reduction to lactams by β-mercaptoethanol were also investigated.It was found that only compounds with electron-rich aromatic rings and specifically an oxa functionality para to the hydroxamic acid nitrogen atom (compounds 1 and 3 - 5) had measurable rates of reduction. 1H NMR spectra recorded during this reaction in D2O buffers (pD 9), however, showed that compounds 1, 2, 6 - 9 (the only ones investigated) formed a hemithioacetal at C-2 even though only 1 has a measurable rate of reduction by the same thiol.The remarkable rate enhancement provided by an oxa functionality suggests that reduction occurs by direct attack of thiolate on the hydroxamic nitrogen of a resonance-stabilized ion pair.

THE REDUCTION OF 2,4-DIHYDROXY-7-METHOXY-1,4-BENZOXAZIN-3-ONE BY THIOLS

2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), a naturally occurring hydroxamic acid involved in pest resistance of cereals, was reduced by thiols to the corresponding lactam.Kinetic studies showed that the reactive species are undissociated DIMBOA and thiolate anion.Possible mechanisms for the reaction are discussed in the light of relative reactivities of DIMBOA and a compound lacking the 7-methoxy substituent, and results from molecular orbital calculations.Key Word Index - Zea mays; Gramineae; 1,4-benzoxazin-3-one; thiols; reduction.