Basic information
- CAS
93-28-7- Standard SMILES
C=CCc1ccc(OC(C)=O)c(OC)c1- InChIKey
SCCDQYPEOIRVGX-UHFFFAOYSA-N- Molecular formula
- C12H14O3
- Average molar mass
- 206.24 g/mol
- Monoisotopic mass
- 206.0942943
Overview
Acetyleugenol is a member of phenols and a benzoate ester.
Names & identifiers
- Preferred name
- Eugenyl Acetate
- IUPAC
- (2-methoxy-4-prop-2-enylphenyl) acetate
- English name
- EUGENOL ACETATE
- Molecular formula
- C12H14O3
- Molecular weight
- 206.24
Names & synonyms
Eugenol acetateEUGENYL ACETATE93-28-7AcetyleugenolAcetyl eugenolPhenol, 2-methoxy-4-(2-propenyl)-, acetatePhenol, 4-allyl-2-methoxy-, acetateFEMA No. 2469V9OSB376X8NSC-1242RefChem:36360202-235-6
Show more names
FEMA 24691-Acetoxy-2-methoxy-4-allylbenzene 1,3,4-Eugenol acetateeugenylACETOEUGENOLO-Acetyleugenol
4-Allyl-2-methoxyphenyl acetateAceteugenol4-Allyl-2-methoxyphenol acetateAceto eugenol1,3,4-Eugenol acetate1-Acetoxy-2-methoxy-4-allylbenzene2-Methoxy-4-(2-propenyl)phenyl acetateEINECS 202-235-6
Database identifiers
- CAS
93-28-7- PubChem CID
- 7136
- DTXSID
DTXSID5052624- ChEMBL
CHEMBL108299- ChEBI
CHEBI:34522- UNII
- V9OSB376X8
- EC Number
- 202-235-6
- Nikkaji
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 35.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 225
Experimental & physicochemical properties
CosmeticsCosmetics ingredient -> Conditioning/Emollient; Flavor; Fragrance
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Eugenyl acetate) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.077-1.082 (supercooled liquid)
Flavoring AgentsEU Flavoring substances
Solubility
Insoluble in water; Soluble in ether, fixed oils
Soluble (in ethanol)
Boiling Point282 °C
Melting Point30 - 31 °C
Refractive Index1.514-1.522 (supercooled liquid)
Physical Description
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1671 reports by companies from 5 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Phenol, 2-methoxy-4-(2-propenyl)-, acetate
Hazard Traits - Fragrance Allergen
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
REACH registered substance: 4-allyl-2-methoxyphenyl acetate (EC: 202-235-6)
Phenol, 2-methoxy-4-(2-propenyl)-, acetate: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- SJ4550000
- hs_code
- 29147000
- Toxicity
- The acute oral LD50 value in rats was reported as 1.67 g/kg (Jenner, Hagan, Taylor, Cook & Fitzhugh, 1964) and as 2.6 g/kg (2.3-2.9 g/kg) (Moreno, 1972b). The acute dermal LD50 value in rabbits exceeded 5 g/kg (Moreno, 1972a).
- risk_code
- 22-38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Uses & manufacturing
Household ProductsCosmetics product ingredient: Phenol, 2-methoxy-4-(2-propenyl)-, acetate (Eugenyl Acetate)
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationPhenol, 2-methoxy-4-(2-propen-1-yl)-, 1-acetate: ACTIVE
Applications
OccurrenceReported found in the essential oils of Laurus nobilis, clove buds and leaves, cassia leaf and cinnamon leaf, root and bark
UsesEugenol Acetate is a constituent of Clove oil, an essential oil from the clove plant, Syzygium aromaticum. Clove oil is a natural analgaesic and antiseptic used primarily in dentistry for its main ingredient Eugenol. Clove oil can also be purchased in pharmacies over the counter, as a home remedy for dental pain relief, mainly toothache; it is also often found in the aromatherapy section of health food stores.
Preparation methods
PreparationBy direct acetylation of eugenol using acetic anhydride.
Upstream & downstream products
Upstream raw materials
Related reactions
9 records
Compound notes
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