Eugenol
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Basic Info
| Common Name | Eugenol(F05575) |
| 2D Structure | |
| Description | Eugenol is an allyl chain-substituted guaiacol, i.e. 2-methoxy-4-(2-propenyl)phenol. Eugenol is a member of the allylbenzene class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like odor. Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from petrochemicals or from by-products of paper manufacture (Wikipedia). |
| FRCD ID | F05575 |
| CAS Number | 97-53-0 |
| PubChem CID | 3314 |
| Formula | C10H12O2 |
| IUPAC Name | 2-methoxy-4-prop-2-enylphenol |
| InChI Key | RRAFCDWBNXTKKO-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3 |
| Canonical SMILES | COC1=C(C=CC(=C1)CC=C)O |
| Isomeric SMILES | COC1=C(C=CC(=C1)CC=C)O |
| Wikipedia | Eugenol |
| Synonyms |
Eugenic acid
2-Methoxy-4-prop-2-enylphenol
eugenol
97-53-0
4-Allyl-2-methoxyphenol
4-Allylguaiacol
Allylguaiacol
Caryophyllic acid
p-Allylguaiacol
p-Eugenol
|
| Classifies |
Pesticide
Veterinary Drug
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Phenols |
| Subclass | Methoxyphenols |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Methoxyphenols |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Methoxyphenol - Phenoxy compound - Methoxybenzene - Phenol ether - Anisole - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Monocyclic benzene moiety - Ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 164.204 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 3 |
| Complexity | 145 |
| Monoisotopic Mass | 164.084 |
| Exact Mass | 164.084 |
| XLogP | 2 |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8736 |
| Human Intestinal Absorption | HIA+ | 0.9832 |
| Caco-2 Permeability | Caco2+ | 0.8629 |
| P-glycoprotein Substrate | Non-substrate | 0.6744 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6684 |
| Non-inhibitor | 0.6287 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8418 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7823 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7523 |
| CYP450 2D6 Substrate | Non-substrate | 0.7857 |
| CYP450 3A4 Substrate | Non-substrate | 0.6383 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5507 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8880 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8828 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5425 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8310 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5110 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8355 |
| Non-inhibitor | 0.9279 | |
| AMES Toxicity | Non AMES toxic | 0.9265 |
| Carcinogens | Non-carcinogens | 0.8432 |
| Fish Toxicity | High FHMT | 0.9431 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9663 |
| Honey Bee Toxicity | High HBT | 0.8095 |
| Biodegradation | Not ready biodegradable | 0.6080 |
| Acute Oral Toxicity | III | 0.8605 |
| Carcinogenicity (Three-class) | Non-required | 0.5959 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.9183 | LogS |
| Caco-2 Permeability | 1.4919 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9616 | LD50, mol/kg |
| Fish Toxicity | 0.8660 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3846 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Crustaceans | Japan | 0.05ppm | |||
| Other Fish | Japan | 0.05ppm | |||
| Perciformes | Japan | 0.05ppm | |||
| Anguilliformes | Japan | 0.05ppm | |||
| Salmoniformes | Japan | 0.05ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| The anticonvulsant and anti-plasmid conjugation potential of Thymus vulgaris chemistry: An in vivo murine and in vitro study. | Food Chem Toxicol | 2018 Oct | 30055314 |
| Trans-Cinnamaldehyde and Eugenol Increase Acinetobacter baumannii Sensitivity to Beta-Lactam Antibiotics. | Front Microbiol | 2018 May 23 | 29875743 |
| Phenylpropenes: Occurrence, Distribution, and Biosynthesis in Fruit. | J Agric Food Chem | 2018 Mar 14 | 28006900 |
| Progress on the Antimicrobial Activity Research of Clove Oil and Eugenol in theFood Antisepsis Field. | J Food Sci | 2018 Jun | 29802735 |
| Characterization of the Potent Odorants Contributing to the Characteristic Aroma of Beijing Douzhi by Gas Chromatography-Olfactometry, Quantitative Analysis, and Odor Activity Value. | J Agric Food Chem | 2018 Jan 24 | 29260548 |
| Semisynthetic Phenol Derivatives Obtained from Natural Phenols: AntimicrobialActivity and Molecular Properties. | J Agric Food Chem | 2018 Jan 10 | 29286652 |
| Carvacrol and eugenol effectively inhibit Rhizopus stolonifer and controlpostharvest soft rot decay in peaches. | J Appl Microbiol | 2018 Jan | 29044849 |
| Effects and interactions of gallic acid, eugenol and temperature on thermalinactivation of Salmonella spp. in ground chicken. | Food Res Int | 2018 Jan | 29389617 |
| The inhibitory effects of essential oil constituents against germination,outgrowth and vegetative growth of spores of Clostridium perfringens type A inlaboratory medium and chicken meat. | Food Microbiol | 2018 Aug | 29526218 |
| Foliar Exposure of Cu(OH)2 Nanopesticide to Basil ( Ocimum basilicum):Variety-Dependent Copper Translocation and Biochemical Responses. | J Agric Food Chem | 2018 Apr 4 | 29558120 |
| Recent advances on polysaccharides, lipids and protein based edible films andcoatings: A review. | Int J Biol Macromol | 2018 Apr 1 | 29155200 |
| Large-Scale Comparative Analysis of Eugenol-Induced/Repressed Genes Expression in <i>Aspergillus flavus</i> Using RNA-seq. | Front Microbiol | 2018 | 29899734 |
| The Usefulness of Non-Toxic Plant Metabolites in the Control of Bacterial Proliferation. | Probiotics Antimicrob Proteins | 2017 Sep | 28357646 |
| Critical Synergistic Concentration of Lecithin Phospholipids Improves theAntimicrobial Activity of Eugenol against Escherichia coli. | Appl Environ Microbiol | 2017 Oct 17 | 28842540 |
| Phytochemical residue profiles in rice grains fumigated with essential oils forthe control of rice weevil. | PLoS One | 2017 Oct 12 | 29023481 |
| Non-target evaluation of contaminants in honey bees and pollen samples by gaschromatography time-of-flight mass spectrometry. | Chemosphere | 2017 Oct | 28679151 |
| Elimination kinetics of eugenol in grass carp in a simulated transportationsetting. | BMC Vet Res | 2017 Nov 21 | 29162104 |
| Antimicrobial activity of eugenol and essential oils containing eugenol: Amechanistic viewpoint. | Crit Rev Microbiol | 2017 Nov | 28346030 |
| Influence of clove oil and eugenol on muscle contraction of silkworm (Bombyxmori). | Drug Discov Ther | 2017 May 30 | 28458297 |
| Microencapsulation of eugenol molecules by β-cyclodextrine as a thermal protection method of antibacterial action. | Mater Sci Eng C Mater Biol Appl | 2017 Jun 1 | 28415462 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- Ogawa Y, Akamatsu M, Hotta Y, Hosoda A, Tamura H: Effect of essential oils, such as raspberry ketone and its derivatives, on antiandrogenic activity based on in vitro reporter gene assay. Bioorg Med Chem Lett. 2010 Apr 1;20(7):2111-4. doi: 10.1016/j.bmcl.2010.02.059. Epub 2010 Feb 21. [20226658 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
References
- Howes MJ, Houghton PJ, Barlow DJ, Pocock VJ, Milligan SR: Assessment of estrogenic activity in some common essential oil constituents. J Pharm Pharmacol. 2002 Nov;54(11):1521-8. [12495555 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
- Gene Name:
- PPARG
- Uniprot ID:
- P37231
- Molecular Weight:
- 57619.58 Da
References
- Fakhrudin N, Ladurner A, Atanasov AG, Heiss EH, Baumgartner L, Markt P, Schuster D, Ellmerer EP, Wolber G, Rollinger JM, Stuppner H, Dirsch VM: Computer-aided discovery, validation, and mechanistic characterization of novel neolignan activators of peroxisome proliferator-activated receptor gamma. Mol Pharmacol. 2010 Apr;77(4):559-66. doi: 10.1124/mol.109.062141. Epub 2010 Jan 11. [20064974 ]
- General Function:
- Calcium channel activity
- Specific Function:
- Putative receptor-activated non-selective calcium permeant cation channel. It is activated by innocuous (warm) temperatures and shows an increased response at noxious temperatures greater than 39 degrees Celsius. Activation exhibits an outward rectification. May associate with TRPV1 and may modulate its activity. Is a negative regulator of hair growth and cycling: TRPV3-coupled signaling suppresses keratinocyte proliferation in hair follicles and induces apoptosis and premature hair follicle regression (catagen).
- Gene Name:
- TRPV3
- Uniprot ID:
- Q8NET8
- Molecular Weight:
- 90635.115 Da
References
- Borbiro I, Lisztes E, Toth BI, Czifra G, Olah A, Szollosi AG, Szentandrassy N, Nanasi PP, Peter Z, Paus R, Kovacs L, Biro T: Activation of transient receptor potential vanilloid-3 inhibits human hair growth. J Invest Dermatol. 2011 Aug;131(8):1605-14. doi: 10.1038/jid.2011.122. Epub 2011 May 19. [21593771 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]