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382051

Sigma-Aldrich

4-Hydroxy-3-methoxycinnamaldehyde

98%

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Synonym(s):
Coniferyl aldehyde
Linear Formula:
HOC6H3(OCH3)CH=CHCHO
CAS Number:
Molecular Weight:
178.18
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

bp

175 °C/5 mmHg (lit.)

mp

80-82 °C (lit.)

SMILES string

COc1cc(\C=C\C=O)ccc1O

InChI

1S/C10H10O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-7,12H,1H3/b3-2+

InChI key

DKZBBWMURDFHNE-NSCUHMNNSA-N

General description

4-Hydroxy-3-methoxycinnamaldehyde is an isoflavonoid. It has been isolated from the insecticidally active hot dichloromethane extract of heartwood of Gliricidia sepium, seed kernels of Melia azedarach L and barks of Cinnamomum cebuense.

Application

4-Hydroxy-3-methoxycinnamaldehyde is suitable for use in a study to investigate the antioxidant and antiradical activities of ferulates using a β-carotene-linoleate model system and a DPPH radical scavenging assay, respectively.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Isoflavonoids and a pterocarpan from< i> Gliricidia sepium</i>.
Herath HMTB, et al.
Phytochemistry, 47(1), 117-119 (1998)
Seikwan Oh et al.
Archives of pharmacal research, 29(6), 469-475 (2006-07-13)
A series of yakuchinone B 1f and its analogs 1a-e was synthesized and evaluated for free radical scavenging, suppression of LPS-induced NO generation, cytotoxicity and anti-excitotoxicity in vitro. Compound 1c exhibited potent anti-excitotoxicity, while all compounds 1a-f showed considerable effects
M Lisa Manier et al.
Journal of the American Society for Mass Spectrometry, 22(8), 1409-1419 (2011-09-29)
Isoniazid (INH) is an important component of front-line anti-tuberculosis therapy with good serum pharmacokinetics but unknown ability to penetrate tuberculous lesions. However, endogenous background interferences hinder our ability to directly analyze INH in tissues. Chemical derivatization has been successfully used
Antioxidant and antiradical activity of ferulates.
Karamac M, et al.
Czech Journal of Food Sciences, 23(2), 469-475 (2005)
María C Carpinella et al.
Journal of agricultural and food chemistry, 53(8), 2922-2927 (2005-04-14)
In the continuous search for antifungal compounds from plants, the hydroxycoumarin scopoletin (1) was isolated from seed kernels of Melia azedarach L. from which three other compounds, vanillin (2), 4-hydroxy-3-methoxycinnamaldehyde (3), and (+/-) pinoresinol (4), have also been isolated. Guided

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