Page last updated: 2024-12-09

(E)-2-methoxycinnamic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

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

ID SourceID
PubMed CID734154
CHEMBL ID95203
CHEBI ID136676
CHEBI ID93692

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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
Brassica napus metaboliteAny plant metabolite that is produced by rapeseed (Brassica napus).
EC 1.14.18.1 (tyrosinase) inhibitorAny 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)

ClassDescription
cinnamic acidsAny alpha,beta-unsaturated monocarboxylic acid based on the cinnamic acid skeleton and its substituted derivatives.
monomethoxybenzeneCompounds 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 IDTitleYearJournalArticle
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & 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.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID158045In vitro inhibition as IC50 against Plasmodium falciparum by [3H]hypoxanthine uptake2002Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4
New anti-malarial compounds from database searching.
AID37266Inhibition of alpha-glucosidase activity2004Bioorganic & medicinal chemistry letters, Jun-07, Volume: 14, Issue:11
Structure-activity relationships of trans-cinnamic acid derivatives on alpha-glucosidase inhibition.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature 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)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (33.33)29.6817
2010's4 (66.67)24.3611
2020's0 (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.

MetricThis Compound (vs All)
Research Demand Index12.56 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]