2D Structure
3D Structure
| Properties | |
|---|---|
| PID | PID00007 |
| Mol. Weight | 164.204 g/mol |
| LogP | 2.49 |
| Water solubility | In water, 2460 mg/L at 25 °C |
| Hydrogen Bond Donor | 1 |
| Hydrogen Bond Acceptor | 2 |
| Rotatable Bonds | 3 |
| XLogP3 | 2.0 |
| Identifiers | |
|---|---|
| Formula | C10H12O2 |
| PubChem CID | 3314 |
| FEMA | 2467 |
| Flavor Profile | Spicy, pungent taste, pleasant, clove-like odor |
| Smiles | COC1=C(C=CC(=C1)CC=C)O |
| InChl Key | RRAFCDWBNXTKKO-UHFFFAOYSA-N |
| InChl | InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3 |
| CAS Registry Number | 97-53-0 |
| IUPAC Systematic Name | 2-methoxy-4-prop-2-enylphenol |
Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets
Note: Known Targets (Gene) from 6952 literatures, DrugBank (http://www.drugbank.ca/), STITCH (http://stitch.embl.de/), ChEMBL (https://www.ebi.ac.uk/chembl/), Therapeutic Target Database (http://bidd.nus.edu.sg/group/ttd/), and Comparative Toxicogenomics Database (CTD, http://ctdbase.org/)
| English Name | Pinyin Name (Chinese Name) | Latin Name | Properties in TCM | merdians | View Graph |
|---|---|---|---|---|---|
| Siebold Wildginger Equivalent plant: Asarum hetero | Xi Xin (细辛) | Asari Radix Et Rhizoma | Warm,Pungent | Lung, Kidney, Heart | View Graph |
| Cassiabarktree Twig | Gui Zhi (桂枝) | Cinnamomi Ramulus | Warm,Pungent,Sweet | Lung,Bladder,Heart | View Graph |
| Chinese Thorowax Equivalent plant: Bupleurum scorz | Chai Hu(柴胡) | Bupleuri Radix | Minor cold, Pungent, Bitter | Liver, Gallbladder, Lung | View Graph |
| Clove Tree | Ding Xiang (丁香) | Caryophylli Flos | Warm,Pungent | Spleen, Stomach, Kidney, Lung | View Graph |
| Cablin Potchouli | Guang Huo Xiang (广藿香) | Pogostemonis Herba | Minor Warm,Pungent | Lung, Spleen, Stomach | View Graph |
| Bunge Pricklyash Equivalent plant: Zanthoxylum sch | Hua Jiao (花椒) | Zanthoxyli Pericarpium | Warm,Pungent | Spleen, Stomach, Kidney | View Graph |
| Myrrh | Mo Yao (没药) | Myrrha | Neutral, Pungent, Bitter | Spleen, Liver, Heart, Kidney | View Graph |
| Subshrubby Peony Bark Equivalent plant: Paeonia de | Mu Dan Pi (牡丹皮) | Moutan Cortex | Minor cold, Pungent, Bitter | Liver, Heart, Kidney | View Graph |
| Fresh Common Ginger | Sheng Jiang (生姜) | Zingiber Rhizoma Recens | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Haichow Elsholtzia | Xiang Ru (香薷) | Moslae Herba | Minor Warm,Pungent | Lung, Stomach | View Graph |
Eugenol is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds. It is a colorless to pale yellow, aromatic oily
liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil and bay leaf. It is present in concentrations of 80C90% in
clove bud oil and at 82C88% in clove leaf oil. Eugenol has a pleasant, spicy, clove-like scent.
Eugenol exhibits antioxidant and anti-inflammatory activities, analgesic activity, alveolar osteitis, antibacterial, acaricidal activities,
antidepressant-like activity, antifungal, antipyretic, promoting transdermal absorption and eliminating mosquitoes, antifungal action
anaesthetic effects,Anthelmintic activity, anaesthetic, antiproliferative agents, inhibits oxidative, inhibits amyloid-induced hemolysis,
Protect Acute Doxorubicin Cardiotoxicity repellent activity,analgesic effects etc.
Note: Click anywhere in the blank, you can drag the whole dynamic diagram. Click on a node, you can drag his location to see it more clearly. The blue circle represents pharmacology, toxicology, or daily use. Orange hexagon represents the pungent compounds.
1. Li Y, She Q, Han Z, et al. Anaesthetic Effects of Eugenol on Grass Shrimp (Palaemonetes sinensis) of Different Sizes at Different Concentrations and Temperatures[J]. Scientific reports, 2018, 8(1): 11007.
2. Saydmohammed M, Pal A K. Anesthetic effect of eugenol and menthol on handling stress in Macrobrachium rosenbergii[J]. Aquaculture, 2009, 298(1-2): 162-167.
3. de Lima Boijink C, da Cunha Miranda W S, Chagas E C, et al. Anthelmintic activity of eugenol in tambaquis with monogenean gill infection[J]. Aquaculture, 2015, 438: 138-140.
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5. Kalmes M, Hennen J, Bl?meke B. Eugenol and isoeugenol as antiproliferative agents in skin cancer cells[J]. Toxicology Letters, 2009 (189): S100.
6. Yan X, Zhang G, Bie F, et al. Eugenol inhibits oxidative phosphorylation and fatty acid oxidation via downregulation of c-Myc/PGC-1/ERR signaling pathway in MCF10A-ras cells[J]. Scientific reports, 2017, 7(1): 12920.
7. Dubey K, Anand B G, Shekhawat D S, et al. Eugenol prevents amyloid formation of proteins and inhibits amyloid-induced hemolysis[J]. Scientific reports, 2017, 7: 40744.
8. Fouad A A, Yacoubi M T. Mechanisms underlying the protective effect of eugenol in rats with acute doxorubicin cardiotoxicity[J]. Archives of pharmacal research, 2011, 34(5): 821.
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11. Yeon K Y, Chung G, Kim Y H, et al. Eugenol reverses mechanical allodynia after peripheral nerve injury by inhibiting hyperpolarization-activated cyclic nucleotide-gated (HCN) channels [J]. Pain, 2011, 152(9): 2108-2116.
12. Li H Y, Lee B K, Kim J S, et al. Eugenol inhibits ATP-induced P2X currents in trigeminal ganglion neurons [J]. The Korean Journal of Physiology & Pharmacology, 2008, 12(6): 315-321.
13. Dal Bo W, Luiz AP, Martins DF, Mazzardo-Martins L, Santos ARS (2012) Eugenol reduces acute pain in mice by modulating the glutamatergic and tumor necrosis factor alpha (TNF-a) pathways.
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15. Jesudasan J S, Ramadorai A K, Wahab P U A. Effect of eugenol in the management of alveolar osteitis: A systematic review[J]. Journal of Oral and Maxillofacial Surgery, Medicine, and Pathology, 2014, 26(2): 101-107.
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17. Irie Y, Itokazu N, Anjiki N, et al. Eugenol exhibits antidepressant-like activity in mice and induces expression of metallothionein-III in the hippocampus[J]. Brain research, 2004, 1011(2): 243-246.
18. Vazquez B I, Fente C, Franco C M, et al. Inhibitory effects of eugenol and thymol on Penicillium citrinum strains in culture media and cheese[J]. International Journal of Food Microbiology, 2001, 67(1-2): 157-163.
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