Ferulic Acid Methyl Ester

  • CAT Number: R030119
  • CAS Number: 2309-07-1
  • Molecular Formula: C11H12O4
  • Molecular Weight: 208.213
  • Purity: ≥95%
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Ferulic acid (CAS&nbsp;2309-07-1) is a hydroxycinnamic acid that is abundant in plants and originally derived from giant fennel (<em>F. communis</em>). This naturally-occurring phenolic has antioxidant activities that provide protection against inflammation and cancer. Ferulic acid methyl ester is a lipophilic derivative of ferulic acid, demonstrating increased ability to cross cell membranes. Ferulic acid methyl ester has less antioxidant capacity than ferulic acid in neuronal PC12 cells (IC<sub>50</sub> = 74.7 &mu;M for ferulic acid ethyl ester <em>vs.</em> 44.6 &mu;M for ferulic acid, 2,2-diphenyl-1-picrylhydrazyl radical scavenging). Ferulic acid methyl ester, at 10-25 &micro;g/ml, inhibits the release of pro-inflammatory cytokines, blocks the expression of COX-2, and reduces nitric oxide generation from LPS-stimulated macrophages.

Catalog Number R030119
CAS Number 2309-07-1
Molecular Formula

C11H12O4

Purity 95%
Storage -20°C
IUPAC Name methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
InChI InChI=1S/C11H12O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3-7,12H,1-2H3/b6-4+
InChIKey AUJXJFHANFIVKH-GQCTYLIASA-N
SMILES COC1=C(C=CC(=C1)C=CC(=O)OC)O
Reference

<p>
<span style="color:#000000;"><span style="font-size:12px;"><span style="font-family:arial,helvetica,sans-serif;">1.Huang, Mou-Tuan, et al. &quot;Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate.&quot;&nbsp;<i style="font-family: Arial, sans-serif; font-size: 13px;">Cancer research</i>&nbsp;48.21 (1988): 5941-5946.<br />
2.Conney, Allan H., et al. &quot;Inhibitory effect of curcumin and some related dietary compounds on tumor promotion and arachidonic acid metabolism in mouse skin.&quot;&nbsp;<i style="font-family: Arial, sans-serif; font-size: 13px;">Advances in enzyme regulation</i>&nbsp;31 (1991): 385-396.<br />
3.Iwahashi, Hideo, Koji Nishizaki, and Ichiro Takagi. &quot;Cytochrome c catalyses the formation of pentyl radical and octanoic acid radical from linoleic acid hydroperoxide.&quot;&nbsp;<i style="font-family: Arial, sans-serif; font-size: 13px;">Biochemical Journal</i>&nbsp;361.1 (2002): 57-66.<br />
4.Sudheer, Adluri Ram, et al. &quot;Influence of ferulic acid on nicotine-induced lipid peroxidation, DNA damage and inflammation in experimental rats as compared to N-acetylcysteine.&quot;&nbsp;<i style="font-family: Arial, sans-serif; font-size: 13px;">Toxicology</i>&nbsp;243.3 (2008): 317-329.<br />
5.Sultana, Rukhsana. &quot;Ferulic acid ethyl ester as a potential therapy in neurodegenerative disorders.&quot;&nbsp;<i style="font-family: Arial, sans-serif; font-size: 13px;">Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease</i>&nbsp;1822.5 (2012): 748-752.<br />
6.Garrido, Jorge, et al. &quot;Alkyl esters of hydroxycinnamic acids with improved antioxidant activity and lipophilicity protect PC12 cells against oxidative stress.&quot;&nbsp;<i style="font-family: Arial, sans-serif; font-size: 13px;">Biochimie</i>&nbsp;94.4 (2012): 961-967.<br />
7.Phuong, Nguyen Thi Mai, Trinh Tat Cuong, and Dang Ngoc Quang. &quot;Anti-inflammatory activity of methyl ferulate isolated from Stemona tuberosa Lour.&quot;&nbsp;<i style="font-family: Arial, sans-serif; font-size: 13px;">Asian Pacific journal of tropical medicine</i>&nbsp;7 (2014): S327-S331.</span></span></span></p>

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