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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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D L Moreira et al.
Phytochemical analysis : PCA, 12(4), 223-225 (2001-11-16)
A simple method for the resolution and subsequent quantitative determination of liriodenine and moupinamide in Mollinedia species was developed using reversed-phase HPLC based on an octadecyl silane-packed column eluted with gradients of methanol and water.
Ping Geng et al.
Analytical and bioanalytical chemistry, 409(10), 2591-2600 (2017-02-06)
Due to the complexity and variation of the chemical constituents in authentic black cohosh (Actaea racemosa) and its potential adulterant species, an accurate and feasible method for black cohosh authentication is not easy. A high-resolution accurate mass (HRAM) LC-MS fingerprinting
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)
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.
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