543551

Sigma-Aldrich

6-Methoxy-2-benzoxazolinone

97%

Empirical Formula (Hill Notation):
C8H7NO3
CAS Number:
Molecular Weight:
165.15
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

97%

mp

151-156 °C (lit.)

SMILES string

COc1ccc2NC(=O)Oc2c1

InChI

1S/C8H7NO3/c1-11-5-2-3-6-7(4-5)12-8(10)9-6/h2-4H,1H3,(H,9,10)

InChI key

MKMCJLMBVKHUMS-UHFFFAOYSA-N

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General description

6-Methoxy-2-benzoxazolinone (MBOA) is obtained by reacting 2-amino-5-methoxyphenol hydrochloride with urea. MOBA is a naturally occurring auxin-inhibiting substance present in maize shoots.

Packaging

1 g in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Hwa Yeon Kim et al.
BMC complementary and alternative medicine, 18(1), 100-100 (2018-03-21)
It is well known that endoplasmic reticulum (ER) stress plays a huge role in development of metabolic diseases. Specially, ER stress-induced cellular dysfunction has a significant involvement in the pathogenesis of human chronic disorders. This study was designed to study...
Structure-activity relationships of benzoxazolinones with respect to auxin-induced growth and auxin-binding protein.
Hoshi-Sakoda, Masako, et al.
Phytochemistry, 37(2), 297-300 (1994)
Elena Lo Piparo et al.
Journal of agricultural and food chemistry, 54(4), 1111-1115 (2006-02-16)
The overall objective of this study is the ecotoxicological characterization of the benzoxazinone 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), the benzoxazolinones benzoxazolin-2-one (BOA) and 6-methoxybenzoxazolin-2-one (MBOA), and their transformation products: phenoxazinones 2-acetylamino-7-methoxy-3H-phenoxazin-3-one (AAMPO), 2-acetylamino-3H-phenoxazin-3-one (AAPO), 2-amino-7-methoxy-3H-phenoxazin-3-one (AMPO), and 2-amino-3H-phenoxazin-3-one (APO); aminophenol 2-aminophenol AP); acetamide...
Thomas Etzerodt et al.
Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes, 43(1), 1-7 (2007-12-29)
Wheat (Triticum aestivum L.) and other cereals produce allelochemicals as natural defense compounds against weeds, fungi, insects and soil-borne diseases. The main benzoxazinoid allelochemical of wheat is 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), bound as beta-glucoside and released upon plant injury. When leached from...
Lars M Hansen
Journal of agricultural and food chemistry, 54(4), 1031-1035 (2006-02-16)
Partial host-plant resistance could make a substantial contribution to reducing the damage caused by economically important grain aphids and, therefore, to reduced insecticide use. Naturally occurring hydroxamic acids, in particular 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), have been shown to be involved in the...

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