Page last updated: 2024-12-10

1,1-dimethylallyl caffeic acid ester

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

Description

1,1-Dimethylallyl caffeic acid ester, also known as **caffeic acid 1,1-dimethylallyl ester** or **CAPE**, is a natural compound found in propolis, a resinous substance produced by honeybees.

Here's why it's important for research:

**Pharmacological Properties:**

* **Antioxidant:** CAPE exhibits strong antioxidant activity, which can help protect cells from damage caused by free radicals.
* **Anti-inflammatory:** CAPE has been shown to suppress inflammation by inhibiting the production of inflammatory mediators like prostaglandins and cytokines.
* **Anti-cancer:** CAPE is being investigated for its potential anti-cancer properties. It has shown promise in laboratory studies against a range of cancer cell lines, including breast, colon, and prostate cancer.
* **Anti-viral:** CAPE has demonstrated antiviral activity against various viruses, including herpes simplex virus and HIV.
* **Neuroprotective:** CAPE has been shown to protect nerve cells from damage caused by oxidative stress and inflammation.
* **Cardioprotective:** CAPE may offer protection against heart disease by improving blood vessel function and reducing inflammation.

**Research Focus:**

* **Mechanisms of Action:** Researchers are actively investigating the specific mechanisms by which CAPE exerts its various pharmacological effects.
* **Therapeutic Potential:** CAPE is being explored as a potential therapeutic agent for a wide range of diseases, including cancer, inflammatory disorders, viral infections, and neurodegenerative diseases.
* **Drug Development:** Studies are underway to develop CAPE-based drugs for clinical use.
* **Safety and Toxicity:** While CAPE is generally considered safe, research is ongoing to assess its long-term safety and potential toxicity.

**Current Research:**

* **Cancer Therapy:** Clinical trials are investigating the use of CAPE in combination with conventional cancer therapies, such as chemotherapy and radiation.
* **Neurodegenerative Diseases:** Research is exploring the potential of CAPE to prevent or delay the progression of Alzheimer's disease, Parkinson's disease, and other neurodegenerative conditions.
* **Inflammatory Bowel Disease (IBD):** CAPE is being studied for its potential to treat IBD, a chronic inflammatory condition affecting the digestive tract.

**Overall:** 1,1-Dimethylallyl caffeic acid ester (CAPE) is a promising natural compound with a diverse range of pharmacological properties. Its potent antioxidant, anti-inflammatory, and anti-cancer activities have made it a target of intense research, with potential for the development of novel therapeutic agents.

1,1-dimethylallyl caffeic acid ester: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5281790
CHEMBL ID471184
CHEBI ID8393
SCHEMBL ID14461142
MeSH IDM0153028

Synonyms (22)

Synonym
3-methyl-2-butenyl caffeate
isoprenyl caffeate
1,1-dimethylallyl caffeic acid ester
cinnamic acid, 3,4-dihydroxy-, 3-methyl-2-butenyl ester
1,1-dacae
118971-61-2
prenyl caffeate
CHEMBL471184
chebi:8393 ,
3-methylbut-2-enyl (e)-3-(3,4-dihydroxyphenyl)prop-2-enoate
100884-13-7
3-methylbut-2-enyl caffeate
caffeic acid 1,1-dimethylallyl ester
SCHEMBL14461142
3-methylbut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate
2-propenoic acid,3-(3,4-dihydroxyphenyl)-,3-methyl-2-buten-1-yl ester,(2e)-
prenyl cis-caffeate
bdbm50030893
J-003986
caffeic acid 1,1-dimethylallyl ester, analytical standard
prenyl cafeate
Q27108066
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
hydroxycinnamic acidAny member of the class of cinnamic acids carrying one or more hydroxy substituents.
[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]

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TransthyretinHomo sapiens (human)EC50 (µMol)21.00005.60007.54298.6000AID1169291
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (2)

Processvia Protein(s)Taxonomy
signal transductionTransthyretinHomo sapiens (human)
purine nucleobase metabolic processTransthyretinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
hormone activityTransthyretinHomo sapiens (human)
protein bindingTransthyretinHomo sapiens (human)
identical protein bindingTransthyretinHomo sapiens (human)
thyroid hormone bindingTransthyretinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
extracellular regionTransthyretinHomo sapiens (human)
extracellular spaceTransthyretinHomo sapiens (human)
azurophil granule lumenTransthyretinHomo sapiens (human)
extracellular exosomeTransthyretinHomo sapiens (human)
extracellular spaceTransthyretinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID1169291Inhibition of TTR V30M mutant (unknown origin) expressed in Escherichia coli assessed as inhibition of amyloid fibril formation by fluorescence assay2014Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21
Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.
AID332490Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 0.001 multiple round of replication at 12.5 ug/ml after 72 hrs1994Journal of natural products, May, Volume: 57, Issue:5
Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate.
AID332494Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as reduction in viral DNA synthesis after 1 multiple round of replication at 60 ug/ml after 18 hrs by agarose gel electrophoresis relative to control1994Journal of natural products, May, Volume: 57, Issue:5
Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate.
AID362056Cytotoxicity against mouse RAW264.7 cells assessed as cell survival after 24 hrs by MTT assay2008Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16
Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages.
AID332486Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 1 multiple round of replication at 12.5 ug/ml after 72 hrs1994Journal of natural products, May, Volume: 57, Issue:5
Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate.
AID332485Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 1 multiple round of replication at 6.25 ug/ml after 72 hrs1994Journal of natural products, May, Volume: 57, Issue:5
Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate.
AID380004Cytotoxicity against mouse P388 cells after 72 hrs by MTT assay2000Journal of natural products, Apr, Volume: 63, Issue:4
A cytotoxic sesquiterpene caffeate from the liverwort Bazzanianovae-zelandiae.
AID332492Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 0.001 multiple round of replication at 50 ug/ml after 72 hrs1994Journal of natural products, May, Volume: 57, Issue:5
Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate.
AID332488Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 1 multiple round of replication at 50 ug/ml after 72 hrs1994Journal of natural products, May, Volume: 57, Issue:5
Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate.
AID332487Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 1 multiple round of replication at 25 ug/ml after 72 hrs1994Journal of natural products, May, Volume: 57, Issue:5
Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate.
AID1169294Inhibition of TTR V30M mutant (unknown origin) expressed in Escherichia coli assessed as inhibition of amyloid fibril formation at 20 uM by fluorescence assay2014Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21
Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.
AID332491Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 0.001 multiple round of replication at 25 ug/ml after 72 hrs1994Journal of natural products, May, Volume: 57, Issue:5
Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate.
AID362058Ratio of EC50 for mouse RAW264.7 cells to EC50 for inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells2008Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16
Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages.
AID332493Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as reduction in viral DNA synthesis after 1 multiple round of replication at 30 ug/ml after 18 hrs by agarose gel electrophoresis relative to control1994Journal of natural products, May, Volume: 57, Issue:5
Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate.
AID362057Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells assessed as nitrite accumulation administered 1 hr before LPS challenge and measured after 24 hrs by Griess reagent assay2008Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16
Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages.
AID332489Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 0.001 multiple round of replication at 6.25 ug/ml after 72 hrs1994Journal of natural products, May, Volume: 57, Issue:5
Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate.
AID1169299Competitive binding to TTR V30M mutant (unknown origin) expressed in Escherichia coli at 1 to 80 uM by fluorescence assay2014Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21
Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (25.00)18.7374
1990's2 (25.00)18.2507
2000's2 (25.00)29.6817
2010's2 (25.00)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: 12.41

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 Index12.41 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.71 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.41)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (11.11%)4.05%
Observational0 (0.00%)0.25%
Other8 (88.89%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]