Eugenol
| Compound Structure: |
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| Synonyms: | 1,3,4-Eugenol; 1-Allyl-3-methoxy-4-hydroxybenzene; 1-Hydroxy-2-methoxy-4-allylbenzene; 1-Hydroxy-2-methoxy-4-prop-2-enylbenzene; 2-Hydroxy-5-allylanisole; 2-Methoxy-4-(2-propen-1-yl)phenol; 2-Methoxy-4-(3-propenyl)phenol; 2-Methoxy-4-allylphenol | ||||||||||||||||||||||||||||||||||||||||||||||||
| Compound ID: | NMPC-1039 | ||||||||||||||||||||||||||||||||||||||||||||||||
| PubChem ID: | |||||||||||||||||||||||||||||||||||||||||||||||||
| Molecular Formula: | C10H12O2 | ||||||||||||||||||||||||||||||||||||||||||||||||
| Canonical SMILES: | COC1=C(C=CC(=C1)CC=C)O | ||||||||||||||||||||||||||||||||||||||||||||||||
| InChIKey: | RRAFCDWBNXTKKO-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||
| About the compound: | Eugenol is a phenylpropanoid, chemically derived from guaiacol with an allyl chain substitution at the para position relative to the hydroxy group. It is a key constituent of clove essential oil and is known for its antibacterial, analgesic, and antioxidant properties. In the field of dentistry, eugenol has been extensively utilized for treating toothache and pulpitis.In addition to its use in dental care, eugenol plays multiple biological roles. It is recognized as an allergen, a human blood serum metabolite, a sensitiser, a component in volatile oils, and a flavouring agent. It also inhibits monoamine oxidase (EC 1.4.3.4), functions as a radical scavenger, and serves as an antibacterial, antineo plastic, apoptosis inducer, anaesthetic, analgesic, voltage-gated sodium channel blocker, NF-kappaB inhibitor, and an anti-inflammatory agent. Structurally, eugenol is a member of the phenylpropanoid class, monomethoxybenzenes, phenols, and alkenylbenzenes, and is functionally related to guaiacol. Eugenol occurs naturally in several plants, including cinnamon, clove, and bay leaves. It has been used topically as an antiseptic and counter-irritant, and in dental preparations alongside zinc oxide for root canal sealing and pain management. While it is not present in any FDA-approved products, including over-the-counter (OTC) offerings, eugenol is noted for its anti-inflammatory, neuroprotective, antipyretic, antioxidant, antifungal, and analgesic properties. Its exact mechanism of action is not fully understood, but it is known to interfere with action potential conduction. Chemically, eugenol (/ˈjuːdʒɪnɒl/) is an allyl chain-substituted guaiacol, belonging to the allylbenzene class. It appears as a colorless to pale yellow, aromatic oily liquid and is extracted from essential oils of several spices, notably clove, nutmeg, cinnamon, basil, and bay leaf. In clove bud oil, eugenol is present at concentrations of 80–90%, and in clove leaf oil, it ranges from 82–88%. Known for its pleasant, spicy, clove-like scent, the name "eugenol" is derived from "Eugenia caryophyllata," the former Linnean nomenclature for cloves, now known as "Syzygiumaromaticum." GHS Hazard Statements • H302 (17.81%): Harmful if swallowed [Warning Acute toxicity, oral] • H315 (21.09%): Causes skin irritation [Warning Skin corrosion/irritation] • H317 (99.93%): May cause an allergic skin reaction [Warning Sensitization, Skin] • H319 (79.97%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] First Aid In case of exposure: EYES: Remove contact lenses, flush with water or saline for 20-30 minutes, seek medical help, transport to hospital immediately. SKIN: Flood with water, wash with soap, seek medical help if symptoms develop. INHALATION: Leave contaminated area, seek medical help if symptoms arise, provide respiratory protection. INGESTION: Do not induce vomiting. Give water if conscious, call hospital or poison control, transport to hospital if advised, ensure airway if unconscious (NTP, 1992). |
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| Properties: |
Chemical and Physical Properties
Source: PubChem |
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| Source Species: |
Ocimum basilicum Tagetes erecta Luffa cylindrica |