Fenchone
| Molecular & Flavor Profile | |
|---|---|
| Common name: | Fenchone |
| IUPAC name: | 2,2,4-trimethylbicyclo[2.2.1]heptan-3-one |
| SMILES: | CC1(C2CCC(C2)(C1=O)C)C |
| CAS: | 4695-62-9, 7787-20-4, 1195-79-5 |
| Flavor Profile: | earthy, cedarleaf, camphor, thuja, herbal, woody, bitter |
| FEMA Flavor Profile: | Floral |
| FEMA Number: | 4519 |
| Taste: | Not Available |
| Odor: | Not Available |
| Functional Groups: | carbonyl compound, ketone |
Physicochemical Properties
- Molecular weight: 152.237 g/mol
- HBD count: 0
- HBA count: 1
- Number of rotatable bonds: 0
- Complexity: 217.0
- Topological Polor Surface Area: 17.1 A^2
- Monoisotopic Mass: 152.12 g/mol
- Exact Mass: 152.12 g/mol
- XlogP: 2.3
- Charge: 0 C(coulomb)
- Heavy Atom Count: 11
- Atom Stereocenter Count: 2
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 2
- 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/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3
- Volume 3D: 130.2
Nomenclature
- Common name: Fenchone
- IUPAC name: 2,2,4-trimethylbicyclo[2.2.1]heptan-3-one
- CAS numbers: 4695-62-9, 7787-20-4, 1195-79-5
- SMILES: CC1(C2CCC(C2)(C1=O)C)C
- InChI: InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3
- FlavorDB/FEMA name: d-FENCHONE
- Synonyms: d-2-Fenchanone; Bicyclo(2 2 1)heptan-2-one, 1,3,3-trimethyl-, (1R)-; Bicyclo(2 2 1)heptan- 2-one, 1,3,3-tri-methyl-, (1S)-; d-Fenchone; D-Fenchone; (+)-. Fenchone; D(+)-Fenchone; 2-Norbornanone, 1,3,3-trimethyl-, (1R,4S)-(+)-; 1,3,3-Trimethylbicyclo(2 2 1)heptan-2-one; (1R)-1,3,3-Trimethylbicyclo(2 2 1). heptan-2-one; d-1,3,3-Trimethyl-2-norbornanone; d-1,3,3-Trimethyl-2-norcamphanone
- FL number: 7.159
- NAS number: 2479
- CoE number: 551
- EINECS number: 225-160-0
- JECFA number: 1396
Description
- Flavor profile: earthy, cedarleaf, camphor, thuja, herbal, woody, bitter
- FooDB flavor profile: herbal, bitter, thuja, earthy, woody, cedarleaf, camphor
- FEMA flavor profile: Floral
- Functional groups: carbonyl compound, ketone
- Bitter compound: Yes
- Source description: d-Fenchone has a camphor-like odor, powerful and sweet and a warm, somewhat bitter, burning taste
Regulatory Status
- CoE status: 1 ppm
- FDA status: 21 CFR 172.515
- JECFA status: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (2004)
Aroma/Taste Threshold Values
- Aroma threshold values: cooling camphoreous, terpy, spicy, sweet mentholic pine-like
- Taste threshold values: Taste characteristics at 5 ppm; cooling camphoreous, with green citrus lime nuances
Natural Occurence
- Occurrence summary: Naturally occurring; Reported in 3 FlavorDB source entities
- Source entity count: 3
- Representative sources: Fennel, Rosemary, Star Anise
- Documented natural occurrence: Thuja plicata, Thuja occidentalis, Thuja standishii, Russian anise, fennel, a few Artemisia varieties (A. frigida, A. verlotorum, A. santolinaefolia), Lavanda stoechas, Lavanda burmannii, and others; the highest levels are found in fennel oil (12 to 19%); two optically active forms have been isolated. Also reported found in basil, caraway, cedar leaf oil, cloves, dill, licorice and thyme
Composition
- Molecular formula: C10H16O
- Molecular composition: C: 0.789, H: 0.106, O: 0.105
- Number of atoms: 11
ADMET Properties
- ADMET Solubility: -3.508
- ADMET Solubility Level: 3.0
- ADMET BBB: 0.344
- ADMET BBB Level: 1.0
- ADMET EXT Hepatotoxic: -3.5504800000000003
- ADMET EXT Hepatotoxic prediction md: True
- ADMET EXT Hepatotoxic applicability: All properties and OPS components are within expected ranges.
- ADMET EXT Hepatotoxic applicability md: 7.66793
- ADMET EXT Hepatotoxic applicability mdpvalue: 0.951894
- ADMET Absorption Level: 0.0
- ADMET EXT PPB: -1.07903
- ADMET EXT PPB prediction: True
- ADMET EXT PPB applicability: All properties and OPS components are within expected ranges.
- ADMET EXT PPB applicability md: 7.2679800000000006
- ADMET EXT PPB applicability mdpvalue: 1.0
- ADMET unknown AlogP98: 0.0
- ADMET AlogP98: 2.497
- ADMET PSA 2D: 17.3
2D/3D Properties
- Number of atoms: 11
- Molecular formula: C10H16O
- Molecular composition: C: 0.789, H: 0.106, O: 0.105
- Molecular mass: 152.12 g/mol
- Energy: 31.15 Kcal/M
- AlogP: 2.497
- LogD: 2.497
- Molecular Solubilty: -2.412
- Number of aromatic bonds: 0
- Number of aromatic rings: 0
- Number of H acceptor: 1
- Number of H acceptor lipinski: 1
- Number of H donor: 0
- Number of H donor lipinski: 0
- Number of H bonds: 0
- Number of rings: 2
- Surface area(SA): 182.12 A^2
- Molecular SASA(Solvent accessible SA): 305.688 A^2
- Radius of gyration: 1.27719 A
- Molecular 3D SASA: 303.394 A^2
Consumption
- Consumption: 10.00 lb
- Individual intake: 0.00000847 mg/kg/day
- Trade association guidelines: 1.657 mg
- IOFI: Nature Identical
Specifications
- Specifications: (JECFA, 2008); Acid value (max); <1.0; Refractive index; 1.460–1.467 (20°C); Appearance; Colorless to pale yellow liquid; Solubility; Soluble in propylene glycol, ethanol ; and vegetable oils; insoluble in water; Assay (min); 97% C10H16O; Specific gravity; 0.940–0.948 (25°C); Boiling point; 192°C
Reported Uses
- Reported uses (ppm): (FEMA, 1994)
-
Food category usual/max:
Food category Usual (ppm) Max (ppm) Alcoholic beverages 0.10 5.00 Gelatins, puddings 3.21 5.44 Baked goods 9.86 13.02 Nonalcoholic beverages 1.08 3.10 Frozen dairy 3.15 5.35 Soft candy 7.25 9.99
Synthesis
- Synthesis: Isolated from cedarleaf oil (thuja oil)
Physical-Chemical Characteristics
- Empirical formula / MW: C10H16O/152.24
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.