Perilla alcohol
| Molecular & Flavor Profile | |
|---|---|
| Common name: | Perilla alcohol |
| IUPAC name: | (4-prop-1-en-2-ylcyclohexen-1-yl)methanol |
| SMILES: | CC(=C)C1CCC(=CC1)CO |
| CAS: | 536-59-4 |
| Flavor Profile: | fatty, terpineol, linalool, green |
| FEMA Flavor Profile: | Fat , Green , Pungent |
| FEMA Number: | 2664 |
| Taste: | Not Available |
| Odor: | Not Available |
| Functional Groups: | hydroxy compound, alcohol, primary alcohol, alkene |
Physicochemical Properties
- Molecular weight: 152.237 g/mol
- HBD count: 1
- HBA count: 1
- Number of rotatable bonds: 2
- Complexity: 179.0
- Topological Polor Surface Area: 20.2 A^2
- Monoisotopic Mass: 152.12 g/mol
- Exact Mass: 152.12 g/mol
- XlogP: 2.1
- Charge: 0 C(coulomb)
- Heavy Atom Count: 11
- Atom Stereocenter Count: 1
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 1
- 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/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3
- Volume 3D: 131.6
Nomenclature
- Common name: Perilla alcohol
- IUPAC name: (4-prop-1-en-2-ylcyclohexen-1-yl)methanol
- CAS numbers: 536-59-4
- SMILES: CC(=C)C1CCC(=CC1)CO
- InChI: InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3
- FlavorDB/FEMA name: p-MENTHA-1,8-DIEN-7-OL
- Synonyms: 1-Cyclohexene-1-methanol, 4-(1-methylethenyl)-; Cyclohex-1-ene-1-methanol, 4-(1-methylethenyl); Dihydrocuminyl alcohol; 1-Hydroxymethyl-4-isopropenyl-1-cyclohexene; 4-Isopropenylcyclohex-1-en-1-ylmethanol; 4-Isopropenyl-cyclohex-1-ene-1-methanol; p-Mentha-1,8-dien-7-ol; 4-(1-Methylethenyl)-1-cyclohexene-1-methanol; Perilla alcohol; Perillol; Perillyl alcohol
- FL number: 2.06
- NAS number: 2664
- CoE number: 2024
- EINECS number: 208-639-9
- JECFA number: 974
Description
- Flavor profile: fatty, terpineol, linalool, green
- FooDB flavor profile: fatty, terpineol, linalool, green
- FEMA flavor profile: Fat, Green, Pungent
- Functional groups: hydroxy compound, alcohol, primary alcohol, alkene
- Bitter compound: No
- Source description: p-Mentha-1,8-dien-7-ol has a characteristic odor similar to linalool and terpineol
Regulatory Status
- CoE status: 5 ppm
- FDA status: 21 CFR 172.515
- JECFA status: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (2002)
Aroma/Taste Threshold Values
- Aroma threshold values: 7 ppm
Natural Occurence
- Occurrence summary: Naturally occurring; Reported in 17 FlavorDB source entities
- Source entity count: 17
- Representative sources: Chamomile, Citrus Peel Oil, Geranium, Hops Oil, Mastic Gum, Lavendar, Berry, Bergamot, Lemon Balm, Spearmint
- Documented natural occurrence: The d- and l-forms occur naturally in gingergrass essential oil; the l-form is found in lavandin and bergamot, while the d-form is found in caraway; also reported found in the essential oils of Juniperus sabina L. and East Indian geranium. Also reported found in citrus peel oils, berries, peppermint oil, Scotch peppermint oil, hop oil, cardamom, laurel, lemon balm, lamb’s let-tuce, mastic gum oil and bullock’s head (Annona reticulata)
Composition
- Molecular formula: C10H16O
- Molecular composition: C: 0.789, H: 0.106, O: 0.105
- Number of atoms: 11
ADMET Properties
- ADMET Solubility: -2.231
- ADMET Solubility Level: 3.0
- ADMET BBB: 0.262
- ADMET BBB Level: 1.0
- ADMET EXT Hepatotoxic: -8.81295
- ADMET EXT Hepatotoxic prediction md: False
- ADMET EXT Hepatotoxic applicability: All properties and OPS components are within expected ranges.
- ADMET EXT Hepatotoxic applicability md: 10.5035
- ADMET EXT Hepatotoxic applicability mdpvalue: 0.0266017
- ADMET Absorption Level: 0.0
- ADMET EXT PPB: -2.46978
- ADMET EXT PPB prediction: False
- ADMET EXT PPB applicability: All properties and OPS components are within expected ranges.
- ADMET EXT PPB applicability md: 10.534
- ADMET EXT PPB applicability mdpvalue: 0.720333
- ADMET unknown AlogP98: 0.0
- ADMET AlogP98: 2.411
- ADMET PSA 2D: 20.815
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: 1.83 Kcal/M
- AlogP: 2.411
- LogD: 2.411
- Molecular Solubilty: -1.945
- 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: 1
- Number of H donor lipinski: 1
- Number of H bonds: 0
- Number of rings: 1
- Surface area(SA): 183.8 A^2
- Molecular SASA(Solvent accessible SA): 348.421 A^2
- Radius of gyration: 1.6844400000000002 A
- Molecular 3D SASA: 327.525 A^2
Consumption
- Consumption: 0.17 lb
- Individual intake: 0.00000014 mg/kg/day
- Trade association guidelines: 0.394 mg
- IOFI: Nature Identical
Specifications
- Specifications: (JECFA, 2008); Appearance; Colorless to pale yellow, dense, oily ; liquid; Refractive index; 1.495–1.505 (20°C); Assay (min); 96%; Solubility; Slightly soluble in water; soluble in ; alcohols and oils; miscible in ethanol ; at room temperature; Boiling point; 119°C (11 mmHg); Specific gravity; 0.956–0.963 (25°C)
Reported Uses
- Reported uses (ppm): (FEMA, 1994)
-
Food category usual/max:
Food category Usual (ppm) Max (ppm) Baked goods 2.00 8.00 Nonalcoholic beverages 0.55 1.75 Frozen dairy 1.05 2.25 Soft candy 2.68 5.69 Gelatins, puddings 1.00 2.00
Synthesis
- Synthesis: The l-form is obtained starting from β-pinene or by reducing perillic aldehyde with zinc dust and acetic acid, followed by saponification of the acetate
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.