Acetyleugenol
| Molecular & Flavor Profile | |
|---|---|
| Common name: | Acetyleugenol |
| IUPAC name: | (2-methoxy-4-prop-2-enylphenyl) acetate |
| SMILES: | CC(=O)OC1=C(C=C(C=C1)CC=C)OC |
| CAS: | 93-28-7 |
| Flavor Profile: | carnation, spice, clove, malt, fresh, floral, woody, sweet |
| FEMA Flavor Profile: | Floral |
| FEMA Number: | 2469 |
| Taste: | Not Available |
| Odor: | Not Available |
| Functional Groups: | ether, alkyl aryl ether, carboxylic acid derivative, carboxylic acid ester, alkene, aromatic compound |
Physicochemical Properties
- Molecular weight: 206.241 g/mol
- HBD count: 0
- HBA count: 3
- Number of rotatable bonds: 5
- Complexity: 225.0
- Topological Polor Surface Area: 35.5 A^2
- Monoisotopic Mass: 206.094 g/mol
- Exact Mass: 206.094 g/mol
- XlogP: 2.3
- Charge: 0 C(coulomb)
- Heavy Atom Count: 15
- Atom Stereocenter Count: 0
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Bond Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently Bonded Unit Count: 1
- InChI: InChI=1S/C12H14O3/c1-4-5-10-6-7-11(15-9(2)13)12(8-10)14-3/h4,6-8H,1,5H2,2-3H3
- Volume 3D: 167.4
Nomenclature
- Common name: Acetyleugenol
- IUPAC name: (2-methoxy-4-prop-2-enylphenyl) acetate
- CAS numbers: 93-28-7
- SMILES: CC(=O)OC1=C(C=C(C=C1)CC=C)OC
- InChI: InChI=1S/C12H14O3/c1-4-5-10-6-7-11(15-9(2)13)12(8-10)14-3/h4,6-8H,1,5H2,2-3H3
- FlavorDB/FEMA name: EUGENYL ACETATE
- Synonyms: Acetyl eugenol; Aceteugenol; 1-Acetoxy-2-methoxy-4-allylbenzene; Acetyleugenol; 4-Allyl-2-methoxyphenol acetate; 4-Allyl-2-methoxyphenyl acetate; Eugenol acetate; 1,3,4-Eugenol acetate; Eugenyl acetate; 2-Methoxy-4-(2-propenyl)phenol ace-tate; Phenol, 4-allyl-2-methoxy-, acetate; Phenol, 2-methoxy-4-(2-propenyl)-, acetate
- FL number: 9.02
- NAS number: 2469
- CoE number: 210
- EINECS number: 202-235-6
- JECFA number: 1531
Description
- Flavor profile: carnation, spice, clove, malt, fresh, floral, woody, sweet
- FooDB flavor profile: carnation, spice, clove, malt, fresh, floral, woody, sweet
- FEMA flavor profile: Floral
- Functional groups: ether, alkyl aryl ether, carboxylic acid derivative, carboxylic acid ester, alkene, aromatic compound
- Bitter compound: No
- Source description: Eugenyl acetate has a characteristic odor reminiscent of clove oil, with a burning, aromatic flavor
Regulatory Status
- CoE status: 10 ppm
- FDA status: 21 CFR 172.515
- JECFA status: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (2005)
Natural Occurence
- Occurrence summary: Naturally occurring; Reported in 12 FlavorDB source entities
- Source entity count: 12
- Representative sources: Lemon Balm, Laurel, Star Anise, Cardamom, Cassia, Cinnamon, Clove, Cumin, Ginger, Nutmeg
- Documented natural occurrence: Reported found in the essential oils of Laurus nobilis, clove buds and leaves, cassia leaf and cinnamon leaf, root and bark
Composition
- Molecular formula: C12H14O3
- Molecular composition: C: 0.699, H: 0.068, O: 0.233
- Number of atoms: 15
ADMET Properties
- ADMET Solubility: -3.029
- ADMET Solubility Level: 3.0
- ADMET BBB: 0.09
- ADMET BBB Level: 1.0
- ADMET EXT Hepatotoxic: -4.73011
- ADMET EXT Hepatotoxic prediction md: False
- ADMET EXT Hepatotoxic applicability: All properties and OPS components are within expected ranges.
- ADMET EXT Hepatotoxic applicability md: 9.086219999999999
- ADMET EXT Hepatotoxic applicability mdpvalue: 0.413971
- ADMET Absorption Level: 0.0
- ADMET EXT PPB: -2.26154
- ADMET EXT PPB prediction: False
- ADMET EXT PPB applicability: All properties and OPS components are within expected ranges.
- ADMET EXT PPB applicability md: 9.71837
- ADMET EXT PPB applicability mdpvalue: 0.955298
- ADMET unknown AlogP98: 0.0
- ADMET AlogP98: 2.589
- ADMET PSA 2D: 35.16
2D/3D Properties
- Number of atoms: 15
- Molecular formula: C12H14O3
- Molecular composition: C: 0.699, H: 0.068, O: 0.233
- Molecular mass: 206.09400000000002 g/mol
- Energy: 17.87 Kcal/M
- AlogP: 2.589
- LogD: 2.589
- Molecular Solubilty: -3.175
- Number of aromatic bonds: 6
- Number of aromatic rings: 1
- Number of H acceptor: 3
- Number of H acceptor lipinski: 3
- Number of H donor: 0
- Number of H donor lipinski: 0
- Number of H bonds: 0
- Number of rings: 1
- Surface area(SA): 234.58 A^2
- Molecular SASA(Solvent accessible SA): 407.023 A^2
- Radius of gyration: 2.58965 A
- Molecular 3D SASA: 396.09 A^2
Consumption
- Consumption: 816.67 lb
- Individual intake: 0.0006920 mg/kg/day
- Trade association guidelines: 4.346 mg
- IOFI: Nature Identical
Specifications
- Specifications: (JECFA, 2008); Acid value (max); 1.0; Melting point; 25°C; Appearance; Fused solid, melts at warm room ; temperature to a pale-yellow liquid; Refractive index; 1.514–1.522 (supercooled liquid); Assay (min); 98% C12H14O3; Solubility; Soluble in ether; fixed oils and ; ethanol; insoluble in water; Boiling point; 182°C; Specific gravity; 1.077–1.082 (supercooled liquid)
Reported Uses
- Reported uses (ppm): (FEMA, 1994)
-
Food category usual/max:
Food category Usual (ppm) Max (ppm) Baked goods 15.98 19.00 Meat products 20.00 25.00 Condiments, relishes 10.00 20.00 Nonalcoholic beverages 1.88 2.83 Frozen dairy 5.65 7.56 Soft candy 6.75 10.63 Gelatins, puddings 5.82 7.78
Synthesis
- Synthesis: By direct acetylation of eugenol using acetic anhydride
Physical-Chemical Characteristics
- Empirical formula / MW: C12H14O3/206.24
Details of "Molecular & Flavor Profile" and physicochemical properties were obtained from PubChem Substance & Compound Databases, FooDB, Flavornet, SuperSweet, and BitterDB. 2D/3D and ADMET properties were obtained with Discovery Studio.