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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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A Schmidt et al.
The Journal of biological chemistry, 274(7), 4273-4280 (1999-02-06)
Hydroxycinnamoyl-CoA:tyramine N-(hydroxycinnamoyl)transferase (THT; EC 2.3.1.110) catalyzes the transfer of hydroxycinnamic acids from the respective CoA esters to tyramine and other amines in the formation of N-(hydroxycinnamoyl)amines. Expression of THT is induced by Phytophthora infestans, the causative agent of late blight
Mari-Anne Newman et al.
The Plant journal : for cell and molecular biology, 29(4), 487-495 (2002-02-16)
Lipopolysaccharide (LPS) is a ubiquitous component of Gram-negative bacteria which has a number of diverse biological effects on eukaryotic cells. In contrast to the large body of work in mammalian and insect cells, the effects of LPS on plant cells
Jae B Park
Journal of medicinal food, 14(3), 226-231 (2011-02-22)
Typheramide (N-caffeoyltyramine) and alfrutamide (N-feruloyltyramine) are phenylpropenoic acid amides found in plants. In this article, typheramide and alfrutamide were isolated from Allium sativum (garlic) and Allium fistulosum (green onion), their chemical structures were confirmed using nuclear magnetic resonance spectroscopic methods
Laura Zacarés et al.
Molecular plant-microbe interactions : MPMI, 20(11), 1439-1448 (2007-11-06)
Inoculation of tomato plants (Solanum lycopersicum cv. Rutgers) with Pseudomonas syringae pv. tomato led to the production of a hypersensitive-like response in this pathovar of tomato. Accumulation of hydroxycinnamic acid amides (HCAA) of tyramine (p-coumaroyltyramine and feruloyltyramine) and dopamine (p-coumaroyldopamine
Fahimeh Moradi-Afrapoli et al.
Natural product communications, 7(6), 753-755 (2012-07-24)
A methanolic extract from aerial parts of Polygonum hyrcanicum (Polygonaceae) showed high activity against Trypanosoma brucei rhodesiense (IC50 = 3.7 microg/mL). Bioassay-guided fractionation of the extract resulted in isolation of cinnamoylphenethyl amides, including N-trans-caffeoyltyramine (1), N-trans-p-coumaroyltyramine (7), and N-trans-feruloyltyramine (8)
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