103012
3-Hydroxy-4-methoxycinnamic acid, predominantly trans
97%
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About This Item
Linear Formula:
HOC6H3(OCH3)CH=CHCO2H
CAS Number:
Molecular Weight:
194.18
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
208-676-0
MDL number:
Assay:
97%
Form:
solid
Quality Level
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
WGK 2
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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
C Castelluccio et al.
The Biochemical journal, 316 ( Pt 2), 691-694 (1996-06-01)
The hydroxycinnamates, intermediates in the phenylpropanoid synthetic pathway, are effective in enhancing the resistance of low-density lipoprotein (LDL) to oxidation in the order caffeic acid > ferulic acid > p-coumaric acid. It is unclear whether the mode of action of
Sandra M Kern et al.
Journal of agricultural and food chemistry, 51(27), 7884-7891 (2003-12-24)
Hydroxycinnamic acids are antioxidant phenolic compounds which are widespread in plant foods, contribute significantly to total polyphenol intakes, and are absorbed by humans. The extent of their putative health benefit in vivo depends largely on their bioavailability. However, the mechanisms