Compounds > Eugenyl benzoate
Page last updated: 2024-12-06

Eugenyl benzoate

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

Eugenyl benzoate is an ester compound formed by the reaction of eugenol and benzoic acid. It is a colorless to pale yellow liquid with a spicy, clove-like odor. It is used as a fragrance in perfumes and cosmetics, and also has potential applications as a natural insecticide and antimicrobial agent. It is studied for its potential to inhibit the growth of bacteria and fungi, as well as its potential to act as a repellent against insects. Research suggests that it may also have antioxidant properties, which could make it useful in the prevention of certain diseases. The compound is synthesized via a simple esterification reaction between eugenol and benzoyl chloride in the presence of a base.'

Cross-References

ID SourceID
PubMed CID62362
CHEMBL ID264141
CHEBI ID174535
SCHEMBL ID357066

Synonyms (63)

Synonym
(2-methoxy-4-prop-2-enylphenyl) benzoate
CHEBI:174535
KBIO1_001308
DIVK1C_006364
SDCCGMLS-0066560.P001
smr000386915
MLS001049077
SPECTRUM_000718
OPREA1_410467
BSPBIO_003005
531-26-0
nsc-408913
eugenol benzoate
p-eugenol, benzoate
eugenyl benzoate
benzoyl eugenol
4-allyl-2-methoxyphenyl benzoate
nsc408913
NCGC00095927-01
KBIO3_002225
KBIO2_001198
KBIOSS_001198
KBIO2_003766
KBIO2_006334
KBIOGR_002009
SPECTRUM3_001313
SPECPLUS_000268
SPBIO_001870
SPECTRUM2_001905
SPECTRUM4_001465
SPECTRUM300157
SPECTRUM5_000109
NCGC00095927-02
CHEMBL264141
eugenyl benzoat
AE-562/13525005
phenol, 2-methoxy-4-(2-propenyl)-, benzoate
HMS2268G13
CCG-38476
unii-yro21e9z35
yro21e9z35 ,
einecs 208-504-4
2-methoxy-4-(2-propenyl)phenyl benzoate
nsc 408913
fema no. 2471
ai3-23236
phenol, 4-allyl-2-methoxy-, benzoate
phenol, 2-methoxy-4-(2-propen-1-yl)-, 1-benzoate
SCHEMBL357066
eugenyl benzoate [fhfi]
ZOGNBLKDKPCKGB-UHFFFAOYSA-N
2-methoxy-4-(prop-2-en-1-yl)phenyl benzoate
AKOS030490315
SR-01000758224-2
sr-01000758224
benzoic acid eugenyl ester, aldrichcpr
phenol, 4-allyl-2-methoxy-, benzoate (8ci)
fema 2471
STL511304
DTXSID70862132
Q27294677
HY-N8579
CS-0148651
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
carbonyl compoundAny compound containing the carbonyl group, C=O. The term is commonly used in the restricted sense of aldehydes and ketones, although it actually includes carboxylic acids and derivatives.
[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 (30)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency25.11890.004023.8416100.0000AID485290
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency56.23410.631035.7641100.0000AID504339
Chain A, Ferritin light chainEquus caballus (horse)Potency25.11895.623417.292931.6228AID485281
LuciferasePhotinus pyralis (common eastern firefly)Potency6.74560.007215.758889.3584AID588342
USP1 protein, partialHomo sapiens (human)Potency39.81070.031637.5844354.8130AID504865
apical membrane antigen 1, AMA1Plasmodium falciparum 3D7Potency31.62280.707912.194339.8107AID720542
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency44.66840.707936.904389.1251AID504333
chromobox protein homolog 1Homo sapiens (human)Potency56.23410.006026.168889.1251AID540317
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency19.95263.548119.542744.6684AID743266
histone-lysine N-methyltransferase 2A isoform 2 precursorHomo sapiens (human)Potency1.12200.010323.856763.0957AID2662
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency35.48130.00798.23321,122.0200AID2551
lethal(3)malignant brain tumor-like protein 1 isoform IHomo sapiens (human)Potency25.11890.075215.225339.8107AID485360
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency5.01190.031610.279239.8107AID884; AID885
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Rap guanine nucleotide exchange factor 4Homo sapiens (human)Potency15.84893.981146.7448112.2020AID720708
GABA theta subunitRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (10)

Processvia Protein(s)Taxonomy
adaptive immune responseRap guanine nucleotide exchange factor 4Homo sapiens (human)
G protein-coupled receptor signaling pathwayRap guanine nucleotide exchange factor 4Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayRap guanine nucleotide exchange factor 4Homo sapiens (human)
calcium-ion regulated exocytosisRap guanine nucleotide exchange factor 4Homo sapiens (human)
regulation of exocytosisRap guanine nucleotide exchange factor 4Homo sapiens (human)
insulin secretionRap guanine nucleotide exchange factor 4Homo sapiens (human)
positive regulation of insulin secretionRap guanine nucleotide exchange factor 4Homo sapiens (human)
regulation of synaptic vesicle cycleRap guanine nucleotide exchange factor 4Homo sapiens (human)
Ras protein signal transductionRap guanine nucleotide exchange factor 4Homo sapiens (human)
regulation of insulin secretionRap guanine nucleotide exchange factor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
guanyl-nucleotide exchange factor activityRap guanine nucleotide exchange factor 4Homo sapiens (human)
protein bindingRap guanine nucleotide exchange factor 4Homo sapiens (human)
cAMP bindingRap guanine nucleotide exchange factor 4Homo sapiens (human)
protein-macromolecule adaptor activityRap guanine nucleotide exchange factor 4Homo sapiens (human)
small GTPase bindingRap guanine nucleotide exchange factor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
cytosolRap guanine nucleotide exchange factor 4Homo sapiens (human)
plasma membraneRap guanine nucleotide exchange factor 4Homo sapiens (human)
membraneRap guanine nucleotide exchange factor 4Homo sapiens (human)
hippocampal mossy fiber to CA3 synapseRap guanine nucleotide exchange factor 4Homo sapiens (human)
plasma membraneRap guanine nucleotide exchange factor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1167368Antileishmanial activity against axenically cultured Leishmania infantum chagasi MHOM/BR/00/1669 promastigotes infected in mouse RAW264.7 cells assessed as inhibition of parasite growth after 48 hrs2014Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21
Thymol and eugenol derivatives as potential antileishmanial agents.
AID323559Partition coefficient, log P of the compound2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Design and synthesis of eugenol derivatives, as potent 15-lipoxygenase inhibitors.
AID1167369Antileishmanial activity against intracellular Leishmania infantum chagasi MHOM/BR/00/1669 amastigotes infected in mouse RAW264.7 cells assessed as inhibition of parasite growth after 48 hrs2014Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21
Thymol and eugenol derivatives as potential antileishmanial agents.
AID323558Inhibition of soybean 15-lipoxygenase2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Design and synthesis of eugenol derivatives, as potent 15-lipoxygenase inhibitors.
AID392785Inhibition of soybean 15-lipoxygenase2009Bioorganic & medicinal chemistry, Feb-15, Volume: 17, Issue:4
Design, synthesis and SAR studies of 4-allyoxyaniline amides as potent 15-lipoxygensae inhibitors.
AID1167371Antileishmanial activity against intracellular Leishmania infantum chagasi MHOM/BR/00/1669 amastigotes infected in BALB/c mouse assessed as inhibition of parasite growth in spleen at 100 mg/kg, ip once daily treated after 30 days post infection for 30 day2014Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21
Thymol and eugenol derivatives as potential antileishmanial agents.
AID1167372Antileishmanial activity against intracellular Leishmania infantum chagasi MHOM/BR/00/1669 amastigotes infected in BALB/c mouse assessed as inhibition of parasite growth in liver at 100 mg/kg, ip once daily treated after 30 days post infection for 30 days2014Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21
Thymol and eugenol derivatives as potential antileishmanial agents.
AID1167370Cytotoxicity against mouse RAW264.7 cells assessed as cell survival at 100 ug/ml after 48 hrs by MTT assay2014Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21
Thymol and eugenol derivatives as potential antileishmanial agents.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (33.33)29.6817
2010's5 (55.56)24.3611
2020's1 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.20

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.20 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.20)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
pentamidine
Pentamidine: Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.. pentamidine : A diether consisting of pentane-1,5-diol in which both hydroxyl hydrogens have been replaced by 4-amidinophenyl groups. A trypanocidal drug that is used for treatment of cutaneous leishmaniasis and Chagas disease.		2.110aromatic ether;
carboxamidine;
diether		anti-inflammatory agent;
antifungal agent;
calmodulin antagonist;
chemokine receptor 5 antagonist;
EC 2.3.1.48 (histone acetyltransferase) inhibitor;
NMDA receptor antagonist;
S100 calcium-binding protein B inhibitor;
trypanocidal drug;
xenobiotic
thymol
Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.		2.110monoterpenoid;
phenols		volatile oil component
methyleugenol
methyleugenol: structure		2.0510phenylpropanoid
acetyleugenol
acetyleugenol: from cloves; inhibits arachidonate-, adrenaline-, & collagen-induced platelet aggregation		2.110benzoate ester;
phenols
estragole
estragole : A phenylpropanoid that is chavicol in which the hydroxy group is replaced by a methoxy group.		2.0510alkenylbenzene;
monomethoxybenzene;
phenylpropanoid		carcinogenic agent;
flavouring agent;
genotoxin;
insect attractant;
plant metabolite
amphotericin b
Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.		2.110antibiotic antifungal drug;
macrolide antibiotic;
polyene antibiotic		antiamoebic agent;
antiprotozoal drug;
bacterial metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Innate Inflammatory Response
[description not available]		02.0510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.0510
Black Fever
[description not available]		02.110
Leishmaniasis, Visceral
A chronic disease caused by LEISHMANIA DONOVANI and transmitted by the bite of several sandflies of the genera Phlebotomus and Lutzomyia. It is commonly characterized by fever, chills, vomiting, anemia, hepatosplenomegaly, leukopenia, hypergammaglobulinemia, emaciation, and an earth-gray color of the skin. The disease is classified into three main types according to geographic distribution: Indian, Mediterranean (or infantile), and African.		02.110
Anemia, Fanconi
[description not available]		02.1310
Fanconi Anemia
Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)		02.1310