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543551

Sigma-Aldrich

6-Methoxy-2-benzoxazolinone

97%

Synonym(s):

6-MBOA, 6-Methoxy-2(3H)-benzoxazolone, 6-Methoxy-3H-benzoxazol-2-one, 6-Methoxybenzo[d]oxazol-2(3H)-one, 6-Methoxybenzoxazolin-2(3H)-one, 6-Methoxybenzoxazolinone

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About This Item

Empirical Formula (Hill Notation):
C8H7NO3
CAS Number:
532-91-2
Molecular Weight:
165.15
MDL number:
MFCD00051726
UNSPSC Code:
12352100
PubChem Substance ID:
24878693
NACRES:
NA.22

Quality Level

100

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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Related Categories

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
J Acharya et al.
Plant disease, 105(4), 752-757 (2020-10-14)
Corn yield reduction following a cereal rye cover crop has been attributed to, among other factors, allelochemicals released from decomposing cereal rye residue. The allelopathic effect of 6-methoxy-2-benzoxazolinone (MBOA) was evaluated on corn seedling growth, mycelial growth of seven pathogenic
On the Synthesis of 6-Methoxy-2-benzoxazolinone.
John DR, et al.
Agricultural and Biological Chemistry, 39(3), 683-685 (1975)
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
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