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17359-54-5 | 2H-1,4-Benzoxazin-3(4H)-one, 2,4-dihydroxy-
CAS No: 17359-54-5 Catalog No: AG001Z1E MDL No:
Product Description
Catalog Number:
AG001Z1E
Chemical Name:
2H-1,4-Benzoxazin-3(4H)-one, 2,4-dihydroxy-
CAS Number:
17359-54-5
Molecular Formula:
C8H7NO4
Molecular Weight:
181.1455
IUPAC Name:
2,4-dihydroxy-1,4-benzoxazin-3-one
InChI:
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
SMILES:
O=C1C(O)Oc2c(N1O)cccc2
Properties
Complexity:
220
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
181.038g/mol
Formal Charge:
0
Heavy Atom Count:
13
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
181.147g/mol
Monoisotopic Mass:
181.038g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
70A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
XLogP3:
0
Literature
| Title | Journal |
|---|---|
| Phylogenomics of the benzoxazinoid biosynthetic pathway of Poaceae: gene duplications and origin of the Bx cluster. | BMC evolutionary biology 20120101 |
| Qualitative characterization of benzoxazinoid derivatives in whole grain rye and wheat by LC-MS metabolite profiling. | Journal of agricultural and food chemistry 20110209 |
| Structure-activity relationship of benzoxazinones and related compounds with respect to the growth inhibition and alpha-amylase activity in cress seedlings. | Journal of plant physiology 20101015 |
| Combined strategy for phytotoxicity enhancement of benzoxazinones. | Journal of agricultural and food chemistry 20100210 |
| Operons. | Cellular and molecular life sciences : CMLS 20091201 |
| Rediscovering the bioactivity and ecological role of 1,4-benzoxazinones. | Natural product reports 20090401 |
| Benzoxazinoid biosynthesis, a model for evolution of secondary metabolic pathways in plants. | Phytochemistry 20090101 |
| Effects of four benzoxazinoids on gibberellin-induced alpha-amylase activity in barley seeds. | Journal of plant physiology 20081201 |
| Benzoxazinoid biosynthesis in dicot plants. | Phytochemistry 20081101 |
| Elucidation of the final reactions of DIMBOA-glucoside biosynthesis in maize: characterization of Bx6 and Bx7. | Plant physiology 20080301 |
| Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA), two naturally occurring benzoxazinones contained in sprouts of Gramineae are potent aneugens in human-derived liver cells (HepG2). | Cancer letters 20070208 |
| Optimization of benzoxazinones as natural herbicide models by lipophilicity enhancement. | Journal of agricultural and food chemistry 20061213 |
| Isolation and synthesis of allelochemicals from gramineae: benzoxazinones and related compounds. | Journal of agricultural and food chemistry 20060222 |
| Determination of benzoxazinone derivatives in plants by combining pressurized liquid extraction-solid-phase extraction followed by liquid chromatography-electrospray mass spectrometry. | Journal of agricultural and food chemistry 20060222 |
| Concentration of benzoxazinoids in roots of field-grown wheat (Triticum aestivum L.) varieties. | Journal of agricultural and food chemistry 20060222 |
| Structure-activity relationship (SAR) studies of benzoxazinones, their degradation products, and analogues. Phytotoxicity on problematic weeds Avena fatua L. and Lolium rigidum Gaud. | Journal of agricultural and food chemistry 20060222 |
| Fate of benzoxazinone allelochemicals in soil after incorporation of wheat and rye sprouts. | Journal of agricultural and food chemistry 20060222 |
| Transformation of benzoxazinones and derivatives and microbial activity in the test environment of soil ecotoxicological tests on Poecilus cupreus and Folsomia candida. | Journal of agricultural and food chemistry 20060222 |
| Hydroxamic acids in Secale cereale L. and the relationship with their antifeedant and allelopathic properties. | Zeitschrift fur Naturforschung. C, Journal of biosciences 20060101 |
| RT-PCR analysis and stress response capacity of transgenic gshI-poplar clones (Populus x canescens) in response to paraquat exposure. | Zeitschrift fur Naturforschung. C, Journal of biosciences 20060101 |
| Hydroxamic acid content and toxicity of rye at selected growth stages. | Journal of chemical ecology 20050801 |
| Detoxification and transcriptome response in Arabidopsis seedlings exposed to the allelochemical benzoxazolin-2(3H)-one. | The Journal of biological chemistry 20050610 |
| Evolution of the indole alkaloid biosynthesis in the genus Hordeum: distribution of gramine and DIBOA and isolation of the benzoxazinoid biosynthesis genes from Hordeum lechleri. | Phytochemistry 20050601 |
| Structure-activity relationship studies of benzoxazinones and related compounds. Phytotoxicity on Echinochloa crus-galli (L.) P. Beauv. | Journal of agricultural and food chemistry 20050601 |
| Gas chromatographic method for the analysis of allelopathic natural products in rye (Secale cereale L.). | Journal of chromatography. A 20050225 |
| Structure-Activity Relationships (SAR) studies of benzoxazinones, their degradation products and analogues. phytotoxicity on standard target species (STS). | Journal of agricultural and food chemistry 20050209 |
| Degradation studies on benzoxazinoids. Soil degradation dynamics of (2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-(2H)- 1,4-benzoxazin-3(4H)-one (DIBOA-Glc) and its degradation products, phytotoxic allelochemicals from Gramineae. | Journal of agricultural and food chemistry 20050209 |
| Differential exudation of two benzoxazinoids--one of the determining factors for seedling allelopathy of Triticeae species. | Journal of agricultural and food chemistry 20050126 |
| Changes over time in the allelochemical content of ten cultivars of rye (Secale cereale L.). | Journal of chemical ecology 20050101 |
| 1,4-benzoxazin-3-one, 2-benzoxazolinone and gallic acid from Calceolaria thyrsiflora Graham and their antibacterial activity. | Zeitschrift fur Naturforschung. C, Journal of biosciences 20050101 |
| The possible role of hydroxylation in the detoxification of atrazine in mature vetiver (Chrysopogon zizanioides Nash) grown in hydroponics. | Zeitschrift fur Naturforschung. C, Journal of biosciences 20050101 |
| Chemical basis for the antifeedant activity of natural hydroxamic acids and related compounds. | Journal of agricultural and food chemistry 20040505 |
| Growth inhibition and root ultrastructure of cucumber seedlings exposed to allelochemicals from rye (Secale cereale). | Journal of chemical ecology 20040301 |
| Allelopathy as a new strategy for sustainable ecosystems development. | Uchu Seibutsu Kagaku 20030601 |
| Molecular characterization and chromosomal localization of cytochrome P450 genes involved in the biosynthesis of cyclic hydroxamic acids in hexaploid wheat. | Molecular genetics and genomics : MGG 20020401 |
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