Skip to Content
MilliporeSigma
All Photos(3)

Key Documents

103012

Sigma-Aldrich

3-Hydroxy-4-methoxycinnamic acid, predominantly trans

97%

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
HOC6H3(OCH3)CH=CHCO2H
CAS Number:
Molecular Weight:
194.18
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

97%

form

solid

mp

230 °C (dec.) (lit.)

functional group

carboxylic acid

SMILES string

COc1ccc(\C=C\C(O)=O)cc1O

InChI

1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+

InChI key

QURCVMIEKCOAJU-HWKANZROSA-N

General description

3-Hydroxy-4-methoxycinnamic acid, predominantly trans is available as white crystals. 3-Hydroxy-4-methoxycinnamic acid is isolated from the aerial part of Artemisia capillaris, Chinese medicinal plant. It is a component of chinese herbal medicine used for a pain killer and stomachic. It is an efficient acetylcholine inhibitor. 3-Hydroxy-4-methoxycinnamic acid is bioactive metabolite of Spilanthes acmella Murr. It increases the resistance of low-density lipoprotein (LDL) to oxidation.

Application

3-Hydroxy-4-methoxycinnamic acid was used in the synthesis of tranilast and various tranilast analogs (cinnamoyl anthranilates) by genetically engineered Saccharomyces cerevisiae yeast strain. It was also used in the synthesis of glycoside compounds by undergoing glycosidation.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

ppe

dust mask type N95 (US), Eyeshields, Gloves


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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Dominik Szwajgier
Zeitschrift fur Naturforschung. C, Journal of biosciences, 68(3-4), 125-132 (2013-07-04)
The ability of 36 phenolic acids and their derivatives to inhibit acetyl- and butyrylcholinesterase was studied. The most efficient acetylcholine inhibitors were: carnosic acid = gentisic acid > 3-hydroxy-4-methoxycinnamic acid = ethyl ferulate = ethyl vanillate = nordihydroguaiaretic acid >
I M Liu et al.
British journal of pharmacology, 129(4), 631-636 (2000-02-22)
Wistar rats with streptozotocin-induced diabetes (STZ-diabetic rats), which is similar to human insulin-dependent diabetic mellitus (IDDM), were employed to investigate the antihyperglycemic action of isoferulic acid. A single intravenous injection of isoferulic acid decreased the plasma glucose in a dose-dependent
Mariana Monteiro et al.
The Journal of nutrition, 137(10), 2196-2201 (2007-09-22)
Chlorogenic acids (CGA) are abundant phenolic compounds in coffee, with caffeoylquinic (CQA), feruloylquinic (FQA), and dicaffeoylquinic (diCQA) acids being the major subclasses. Despite the potential biopharmacological properties attributed to these compounds, little is known about their bioavailability in humans. In
Jonathan M Hodgson et al.
The British journal of nutrition, 91(2), 301-306 (2004-02-06)
Tea and coffee are rich in polyphenols with a variety of biological activities. Many of the demonstrated activities are consistent with favourable effects on the risk of chronic diseases. 4-O-methylgallic acid (4OMGA) and isoferulic acid are potential biomarkers of exposure
Adriana Farah et al.
The Journal of nutrition, 138(12), 2309-2315 (2008-11-22)
Chlorogenic acids (CGA) are cinnamic acid derivatives with biological effects mostly related to their antioxidant and antiinflammatory activities. Caffeoylquinic acids (CQA) and dicaffeoylquinic acids (diCQA) are the main CGA found in nature. Because green coffee is a major source of

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service