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SMB00196

Sigma-Aldrich

Moupinamide

≥95% (LC/MS-ELSD)

Synonym(s):

Feruloyltyramine, N-Feruloyltyramine, N-trans-Feruloyltyramine, Alfrutamide

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About This Item

Empirical Formula (Hill Notation):
C18H19NO4
CAS Number:
66648-43-9
Molecular Weight:
313.35
MDL number:
MFCD17214811
UNSPSC Code:
12352205
PubChem Substance ID:
329824859
NACRES:
NA.25

Assay

≥95% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

COc1cc(\C=C\C(=O)NCCc2ccc(O)cc2)ccc1O

InChI

1S/C18H19NO4/c1-23-17-12-14(4-8-16(17)21)5-9-18(22)19-11-10-13-2-6-15(20)7-3-13/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5+

InChI key

NPNNKDMSXVRADT-WEVVVXLNSA-N

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General description

Natural product derived from plant source.

Biochem/physiol Actions

Moupinamide, also known as N-feruloyltyramine, alfrutamide, is an inhibitor of COX 1 and COX 2 and has potential antioxidant properties.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Mai Efdi et al.
Bioorganic & medicinal chemistry, 15(11), 3667-3671 (2007-04-03)
Four compounds were isolated from Enicosanthum membranifolium. The structures of the compounds were confirmed by spectroscopic data. Their structures were determined as N-trans-feruloyltyramine, R-(-)-mellein, clerodermic acid, and salicifoline chloride as a quaternary alkaloid compound. The structures of R-(-)-mellein and salicifoline
Mai Efdi et al.
Biological & pharmaceutical bulletin, 30(10), 1972-1974 (2007-10-06)
In this study, we examined the effect of N-trans-feruloyltyramine (FA) on melanogenesis in mouse B16 melanoma cells. Melanogenesis was inhibited by FA in a dose-dependent manner. FA exhibited a greater potency than kojic acid as a standard inhibitor of melanogenesis.
Russell R King et al.
Phytochemistry, 66(20), 2468-2473 (2005-09-03)
Four feruloyl amides, N-trans-feruloyloctopamine (1), N-cis-feruloyloctopamine (2), N-trans-feruloyltyramine (3), N-cis-feruloyltyramine (4), a cross-linked N-trans-feruloyltyramine dimer (5), and a cross-linked N-cis-feruloyltyramine dimer (6) were isolated from potato common scab lesions. The compounds were purified by TLC and characterized by a combination
Jae B Park
Journal of agricultural and food chemistry, 57(19), 8868-8872 (2009-10-08)
Garlic (Allium sativum) is a medicinal and culinary plant reported to have several positive health effects on cardiovascular diseases, particularly via suppressing platelet activation. Therefore, active compounds inhibiting platelet activation were isolated from garlic extract using a P-selectin expression suppressing
Russell R King et al.
Phytochemistry, 71(17-18), 2187-2189 (2010-10-30)
(1)H NMR analysis established that a potential suberin intermediate isolated from potato common scab lesions contained three O-methyl groups, a phenylcoumaran-type linkage and a conjugated trans double bond. Mass spectral data determined its molecular formula as indicative of a dehydrotrimer
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