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532-91-2,MFCD00051726
Catalog No.:AA003N70

532-91-2 | 6-Methoxy-2-benzoxazolinone

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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003N70
Chemical Name:
6-Methoxy-2-benzoxazolinone
CAS Number:
532-91-2
Molecular Formula:
C8H7NO3
Molecular Weight:
165.1461
MDL Number:
MFCD00051726
SMILES:
COc1ccc2c(c1)oc(=O)[nH]2
Properties
Properties
 
BP:
292.97°C (rough estimate)  
Form:
Solid  
MP:
151-156°C(lit.);  
Refractive Index:
1.5468 (estimate)  

Computed Properties
 
Complexity:
195  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
12  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
1  
XLogP3:
1.1  

Downstream Synthesis Route

[1]YakugakuZasshi/JournalofthePharmaceuticalSocietyofJapan,1956,vol.76,p.1002,1004    Chem.Abstr.,1957,p.2738

[1]Koyamaetal.[YakugakuZasshi/JournalofthePharmaceuticalSocietyofJapan,1956,vol.76,p.1002,1004][Chem.Abstr.,1957,p.2738]

[1]YakugakuZasshi/JournalofthePharmaceuticalSocietyofJapan,1956,vol.76,p.1002,1004    Chem.Abstr.,1957,p.2738

[1]Kinugawaetal.[YakugakuZasshi/JournalofthePharmaceuticalSocietyofJapan,1959,vol.79,p.931][Chem.Abstr.,1960,p.497]

Literature

Title: Benzoxazinoids from Scoparia dulcis (sweet broomweed) with antiproliferative activity against the DU-145 human prostate cancer cell line.

Journal: Phytochemistry 20121101

Title: Strong pituitary and hypothalamic responses to photoperiod but not to 6-methoxy-2-benzoxazolinone in female common voles (Microtus arvalis).

Journal: General and comparative endocrinology 20121101

Title: Concentrations and allelopathic effects of benzoxazinoid compounds in soil treated with rye (Secale cereale) cover crop.

Journal: Journal of agricultural and food chemistry 20120509

Title: Antinociceptive and anti-inflammatory effects of octacosanol from the leaves of Sabicea grisea var. grisea in mice.

Journal: International journal of molecular sciences 20120101

Title: Effect of the aqueous extract of Senecio biafrae (Oliv. & Hiern) J. Moore on sexual maturation of immature female rat.

Journal: BMC complementary and alternative medicine 20120101

Title: Benzoxazinoids in root exudates of maize attract Pseudomonas putida to the rhizosphere.

Journal: PloS one 20120101

Title: Rabbit sexual behavior, semen and sperm characteristics when supplemented with sprouted wheat.

Journal: Animal reproduction science 20111201

Title: Allelochemical stress inhibits growth, leaf water relations, PSII photochemistry, non-photochemical fluorescence quenching, and heat energy dissipation in three C3 perennial species.

Journal: Journal of experimental botany 20110801

Title: Is the basal area of maize internodes involved in borer resistance?

Journal: BMC plant biology 20110101

Title: In vitro grown sheep preantral follicles yield oocytes with normal nuclear-epigenetic maturation.

Journal: PloS one 20110101

Title: 2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) and 6-methoxy-benzoxazolin-2-one (MBOA) levels in the wheat rhizosphere and their effect on the soil microbial community structure.

Journal: Journal of agricultural and food chemistry 20101222

Title: Structure-activity relationship of benzoxazinones and related compounds with respect to the growth inhibition and alpha-amylase activity in cress seedlings.

Journal: Journal of plant physiology 20101015

Title: Energy or information? The role of seed availability for reproductive decisions in edible dormice.

Journal: Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology 20100301

Title: Melatonin and structurally-related compounds protect synaptosomal membranes from free radical damage.

Journal: International journal of molecular sciences 20100101

Title: Antioxidant activity of benzoxazolinonic and benzothiazolinonic derivatives in the LDL oxidation model.

Journal: Bioorganic & medicinal chemistry 20091115

Title: Allelochemicals in rye (Secale cereale L.): cultivar and tissue differences in the production of benzoxazinoids and phenolic acids.

Journal: Natural product communications 20090201

Title: Identification of human GnIH homologs, RFRP-1 and RFRP-3, and the cognate receptor, GPR147 in the human hypothalamic pituitary axis.

Journal: PloS one 20090101

Title: Effects of four benzoxazinoids on gibberellin-induced alpha-amylase activity in barley seeds.

Journal: Journal of plant physiology 20081201

Title: Mutations in lipopolysaccharide biosynthetic genes impair maize rhizosphere and root colonization of Rhizobium tropici CIAT899.

Journal: Environmental microbiology 20080501

Title: Development of a pressurized liquid extraction-solid-phase extraction followed by liquid chromatography-electrospray ionization tandem mass spectrometry method for the quantitative determination of benzoxazolinones and their degradation products in agricultural soil.

Journal: Journal of chromatography. A 20080201

Title: 6-MBOA affects testis size, but not delayed-type hypersensitivity, in white-footed mice (Peromyscus leucopus).

Journal: Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20080201

Title: cis-Jasmone induces accumulation of defence compounds in wheat, Triticum aestivum.

Journal: Phytochemistry 20080101

Title: Transformation kinetics of 6-methoxybenzoxazolin-2-one in soil.

Journal: Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes 20080101

Title: Influence of supplemental dietary sprouted wheat on reproduction in artificially inseminated doe rabbits.

Journal: Animal reproduction science 20070501

Title: Effects of the benzoxazoid DIMBOA, selected degradation products, and structure-related pesticides on soil organisms.

Journal: Ecotoxicology and environmental safety 20060901

Title: Administration of 6-methoxybenzoxazolinone (MBOA) does not augment ovulatory responses in St. Croix White ewes superovulated with PMSG.

Journal: Animal reproduction science 20060701

Title: Possible mechanism of inhibition of 6-methoxy-benzoxazolin-2(3H)-one on germination of cress (Lepidium sativum L.).

Journal: Journal of chemical ecology 20060501

Title: Induction of beta-glucosidase activity in maize coleoptiles by blue light illumination.

Journal: Journal of plant physiology 20060301

Title: Determination of benzoxazinone derivatives in plants by combining pressurized liquid extraction-solid-phase extraction followed by liquid chromatography-electrospray mass spectrometry.

Journal: Journal of agricultural and food chemistry 20060222

Title: Concentration of benzoxazinoids in roots of field-grown wheat (Triticum aestivum L.) varieties.

Journal: Journal of agricultural and food chemistry 20060222

Title: Quantification of benzoxazinone derivatives in wheat (Triticum aestivum) varieties grown under contrasting conditions in Denmark.

Journal: Journal of agricultural and food chemistry 20060222

Title: Effect of 6-methoxybenzoxazolin-2-one (MBOA) on the reproduction rate of the grain aphid (Sitobion avenae F.).

Journal: Journal of agricultural and food chemistry 20060222

Title: Effects of some benzoxazinoids on in vitro growth of Cephalosporium gramineum and other fungi pathogenic to cereals and on Cephalosporium stripe of winter wheat.

Journal: Journal of agricultural and food chemistry 20060222

Title: Joint action of benzoxazinone derivatives and phenolic acids.

Journal: Journal of agricultural and food chemistry 20060222

Title: Herbicidal effects of soil-incorporated wheat.

Journal: Journal of agricultural and food chemistry 20060222

Title: Fate of benzoxazinone allelochemicals in soil after incorporation of wheat and rye sprouts.

Journal: Journal of agricultural and food chemistry 20060222

Title: Elucidating the transformation pattern of the cereal allelochemical 6-methoxy-2-benzoxazolinone (MBOA) and the trideuteriomethoxy analogue [D3]-MBOA in soil.

Journal: Journal of agricultural and food chemistry 20060222

Title: Transformation of benzoxazinones and derivatives and microbial activity in the test environment of soil ecotoxicological tests on Poecilus cupreus and Folsomia candida.

Journal: Journal of agricultural and food chemistry 20060222

Title: Influence of the soil composition on the effects of benzoxazinoid allelochemicals on two soil nontarget organisms.

Journal: Journal of agricultural and food chemistry 20060222

Title: Ecotoxicological effects of benzoxazinone allelochemicals and their metabolites on aquatic nontarget organisms.

Journal: Journal of agricultural and food chemistry 20060222

Title: QSAR models for Daphnia magna toxicity prediction of benzoxazinone allelochemicals and their transformation products.

Journal: Journal of agricultural and food chemistry 20060222

Title: Glucosides from MBOA and BOA detoxification by Zea mays and Portulaca oleracea.

Journal: Journal of natural products 20060101

Title: Effects of 6-methoxy-2-benzoxazolinone on the germination and alpha-amylase activity in lettuce seeds.

Journal: Journal of plant physiology 20051201

Title: Hydroxamic acid content and toxicity of rye at selected growth stages.

Journal: Journal of chemical ecology 20050801

Title: Dissecting defense-related and developmental transcriptional responses of maize during Ustilago maydis infection and subsequent tumor formation.

Journal: Plant physiology 20050701

Title: Accumulation of HDMBOA-Glc is induced by biotic stresses prior to the release of MBOA in maize leaves.

Journal: Phytochemistry 20041101

Title: Degradation studies on benzoxazinoids. Soil degradation dynamics of 2,4-dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (DIMBOA) and its degradation products, phytotoxic allelochemicals from gramineae.

Journal: Journal of agricultural and food chemistry 20041020

Title: Antifungal compounds from the root and root exudate of Zea mays.

Journal: Bioscience, biotechnology, and biochemistry 20040601

Title: Rhizobium etli maize populations and their competitiveness for root colonization.

Journal: Archives of microbiology 20040501

Title: Microbial transformation products of benzoxazolinone and benzoxazinone allelochemicals--a review.

Journal: Chemosphere 20040201

Title: Cytotoxic diterpenes from Scoparia dulcis.

Journal: Journal of natural products 20030701

Title: Demonstration of antifungal and anti-human immunodeficiency virus reverse transcriptase activities of 6-methoxy-2-benzoxazolinone and antibacterial activity of the pineal indole 5-methoxyindole-3-acetic acid.

Journal: Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 20020601

Title: Examination of pineal indoles and 6-methoxy-2-benzoxazolinone for antioxidant and antimicrobial effects.

Journal: Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 20011101

Title: Yusheng Hu, et al. Coixol Suppresses NF-κB, MAPK Pathways and NLRP3 Inflammasome Activation in Lipopolysaccharide-Induced RAW 264.7 Cells. Molecules

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