Page last updated: 2024-12-09
(E)-2-methoxycinnamic acid
Description
## (E)-2-methoxycinnamic acid: A Versatile Compound with Research Significance
(E)-2-methoxycinnamic acid, also known as **ferulic acid**, is a naturally occurring phenolic compound found in various plants, particularly in the cell walls of grasses, rice, and wheat. It's a **hydroxycinnamic acid**, a class of organic compounds with significant biological activity.
**Why is it important for research?**
Ferulic acid's importance in research stems from its diverse range of **biological activities**, including:
* **Antioxidant:** It scavenges free radicals, protects against oxidative stress, and may reduce the risk of chronic diseases like cancer and heart disease.
* **Anti-inflammatory:** It inhibits the production of inflammatory mediators, reducing inflammation and pain.
* **Antimicrobial:** It exhibits antimicrobial activity against various bacteria, fungi, and viruses.
* **Neuroprotective:** It protects nerve cells from damage, potentially contributing to improved cognitive function and preventing neurodegenerative diseases.
* **Anti-cancer:** It has shown promising results in inhibiting cancer cell growth and promoting apoptosis (programmed cell death).
* **Cardioprotective:** It improves cardiovascular health by lowering blood pressure, cholesterol levels, and inflammation.
* **Anti-diabetic:** It may help regulate blood sugar levels and improve insulin sensitivity.
**Research Applications:**
Ferulic acid's diverse properties have led to its exploration in various research fields, including:
* **Medicine:** Development of new drugs for treating cancer, inflammation, neurological disorders, and cardiovascular diseases.
* **Food Science:** Enhancement of food preservation and quality through its antioxidant and antimicrobial activity.
* **Cosmetics:** Incorporation in skincare products for its antioxidant and anti-aging properties.
* **Agriculture:** Bio-fertilizers and plant growth regulators to improve crop yields and resilience.
**Current Research Trends:**
Current research focuses on:
* **Improving its bioavailability:** Finding ways to deliver ferulic acid effectively to the body.
* **Developing novel synthetic derivatives:** Creating new compounds with enhanced activity and reduced side effects.
* **Exploring its synergistic effects:** Understanding how it interacts with other compounds to enhance therapeutic outcomes.
**In conclusion,** (E)-2-methoxycinnamic acid, or ferulic acid, is a multifaceted compound with significant potential for research and development. Its diverse biological activities make it a promising candidate for various applications, leading to advancements in medicine, food science, cosmetics, and agriculture.
(E)-2-methoxycinnamic acid : A member of the class of cinnamic acids that is trans-cinnamic acid carrying a methoxy substituent at position 2 on the benzene ring. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
Cross-References
Synonyms (70)
Synonym |
CHEMBL95203 |
coumarinic acid methyl ether |
LS-13766 |
nsc-638141 |
6099-03-2 |
nsc8135 |
nsc-8135 |
cinnamic acid, o-methoxy- |
2-propenoic acid, 3-(2-methoxyphenyl)- |
2-propenoic acid, 3-(2-methoxyphenyl)-, (e)- |
(e)-3-(2-methoxyphenyl)-2-propenoic acid |
2-methoxycinnamic acid |
(e)-3-(2-methoxyphenyl)prop-2-enoic acid |
nsc638141 |
o-methoxycinnamic acid |
2-methoxycinnamic acid, predominantly trans, 98% |
trans-2-methoxycinnamic acid |
2-methoxycinnamic acid, >=97.0% |
(2e)-3-(2-methoxyphenyl)prop-2-enoic acid |
STK411567 |
CHEBI:136676 |
(e)-3-(2-methoxyphenyl)acrylic acid , |
(e)-o-methoxycinnamic acid |
(e)-2-methoxycinnamic acid |
CD9AA602-23B3-4A72-B198-69C984F1152A |
M0449 |
trans-o-methyl-o-cumaric acid |
1011-54-7 |
trans-o-methyl-o-coumaric acid |
HMS1748N22 |
3-(2-methoxyphenyl)prop-2-enoic acid |
AKOS000120225 |
BBL013998 |
3-(2-methoxyphenyl)acrylic acid |
j77sk1y4my , |
ai3-11206 |
2-propenoic acid, 3-(2-methoxyphenyl)-, (2e)- |
einecs 213-785-1 |
unii-j77sk1y4my |
nsc 638141 |
einecs 228-047-4 |
S5758 |
(e)-3-(2-methoxy-phenyl)-acrylic acid |
2-methoxy-zimtsaure |
4-epi-anhydrotetracyclinehydrochloride |
2-methoxy-cinnamic acid |
3-(2-methoxyphenyl)-2-propenoic acid |
(2e)-3-(2-methoxyphenyl)-2-propenoic acid # |
BS-3963 |
AC-34401 |
2-methoxycinnamic acid; ai3-11206 |
J-509858 |
mfcd00064238 |
CHEBI:93692 |
J-008350 |
nci-8135 |
Q63392780 |
(e)-3-(2-methoxyphenyl)acrylicacid |
EN300-16920 |
EN300-833000 |
CS-0016806 |
HY-N1386 |
H10727 |
2-methoxycinnamic acid (predominantly trans) |
DTXSID60901605 |
(2e)-3-(2-methoxyphenyl)-2-propenoic acid |
trans-2-ethoxycinnamic acid |
BAA01154 |
A913664 |
Z2311574127 |
Roles (2)
Role | Description |
Brassica napus metabolite | Any plant metabolite that is produced by rapeseed (Brassica napus). |
EC 1.14.18.1 (tyrosinase) inhibitor | Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals. |
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Drug Classes (2)
Class | Description |
cinnamic acids | Any alpha,beta-unsaturated monocarboxylic acid based on the cinnamic acid skeleton and its substituted derivatives. |
monomethoxybenzene | Compounds containing a benzene skeleton substituted with one methoxy group. |
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Bioassays (7)
Assay ID | Title | Year | Journal | Article |
AID540299 | A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis | 2010 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. |
AID588519 | A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities | 2011 | Antiviral research, Sep, Volume: 91, Issue:3
| High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. |
AID977599 | Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM | 2013 | Molecular pharmacology, Jun, Volume: 83, Issue:6
| Structure-based identification of OATP1B1/3 inhibitors. |
AID977602 | Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM | 2013 | Molecular pharmacology, Jun, Volume: 83, Issue:6
| Structure-based identification of OATP1B1/3 inhibitors. |
AID158045 | In vitro inhibition as IC50 against Plasmodium falciparum by [3H]hypoxanthine uptake | 2002 | Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4
| New anti-malarial compounds from database searching. |
AID37266 | Inhibition of alpha-glucosidase activity | 2004 | Bioorganic & medicinal chemistry letters, Jun-07, Volume: 14, Issue:11
| Structure-activity relationships of trans-cinnamic acid derivatives on alpha-glucosidase inhibition. |
AID1159550 | Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening | 2015 | Nature cell biology, Nov, Volume: 17, Issue:11
| 6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Research
Studies (6)
Timeframe | Studies, This Drug (%) | All Drugs % |
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 2 (33.33) | 29.6817 |
2010's | 4 (66.67) | 24.3611 |
2020's | 0 (0.00) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Market Indicators
Research Demand Index: 12.56
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
Metric | This Compound (vs All) |
---|
Research Demand Index | 12.56 (24.57) | Research Supply Index | 1.95 (2.92) | Research Growth Index | 4.51 (4.65) | Search Engine Demand Index | 0.00 (26.88) | Search Engine Supply Index | 0.00 (0.95) |
| |
Study Types
Publication Type | This drug (%) | All Drugs (%) |
Trials | 0 (0.00%) | 5.53% |
Reviews | 1 (16.67%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 5 (83.33%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |