Dihydrocarveol
| Molecular & Flavor Profile | |
|---|---|
| Common name: | Dihydrocarveol |
| IUPAC name: | 2-methyl-5-prop-1-en-2-ylcyclohexan-1-ol |
| SMILES: | CC1CCC(CC1O)C(=C)C |
| CAS: | 619-01-2, 38049-26-2 |
| Flavor Profile: | mint, spice, herbal, menthol, minty, spearmint |
| FEMA Flavor Profile: | Not Available |
| FEMA Number: | Not Available |
| Taste: | Not Available |
| Odor: | Not Available |
| Functional Groups: | hydroxy compound, alcohol, secondary alcohol, alkene |
Physicochemical Properties
- Molecular weight: 154.253 g/mol
- HBD count: 1
- HBA count: 1
- Number of rotatable bonds: 1
- Complexity: 151.0
- Topological Polor Surface Area: 20.2 A^2
- Monoisotopic Mass: 154.136 g/mol
- Exact Mass: 154.136 g/mol
- XlogP: 3.0
- Charge: 0 C(coulomb)
- Heavy Atom Count: 11
- Atom Stereocenter Count: 3
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 3
- 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/C10H18O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-11H,1,4-6H2,2-3H3
- Volume 3D: 133.5
Nomenclature
- Common name: Dihydrocarveol
- IUPAC name: 2-methyl-5-prop-1-en-2-ylcyclohexan-1-ol
- CAS numbers: 619-01-2, 38049-26-2
- SMILES: CC1CCC(CC1O)C(=C)C
- InChI: InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-11H,1,4-6H2,2-3H3
- FlavorDB/FEMA name: DIHYDROCARVEOL
- Synonyms: 6-Methyl-3-isopropenylcyclohexanol; Tuberyl alcohol; Cyclohexanol, 2-methyl-5-(1-methylethenyl)-; Dihydrocarveol; 1,6-Dihydrocarveol; p-Menth-8-en-2-ol; 8-p-Menthen-2-ol; 2-Methyl-5-(1-methylethenyl)cyclohexanol
- FL number: 2.061
- NAS number: 2379
- CoE number: 2025
- EINECS number: 210-575-1
- JECFA number: 378
Regulatory Status
- CoE status: 200 ppm
- FDA status: 21 CFR 172.515
- JECFA status: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (1998)
Aroma/Taste Threshold Values
- Taste threshold values: Taste characteristics at 15 ppm; green mint with sweet weedy spicy nuances
Natural Occurence
- Occurrence summary: Naturally occurring; Reported in 14 FlavorDB source entities
- Source entity count: 14
- Representative sources: Black Tea, Mentha Oil, Artemisia, Dill, Mint, Rosemary, Spearmint, Scotch Spearmint, Caraway, Celery
- Documented natural occurrence: Reported found (free or esterified) in the essential oils Mentha longifolia, Mentha verticillata, Artemisia jun-cea, caraway (Mentha virdis var. sativa) cultivated in Calabria, spearmint oil and spearmint scotch oil. Also reported found in black tea, dill herb, celery leaf and stalk, caraway seed and rosemary
Composition
- Molecular formula: C10H18O
- Molecular composition: C: 0.779, H: 0.118, O: 0.104
- Number of atoms: 11
ADMET Properties
- ADMET Solubility: -2.492
- ADMET Solubility Level: 3.0
- ADMET BBB: 0.315
- ADMET BBB Level: 1.0
- ADMET EXT Hepatotoxic: -9.74001
- ADMET EXT Hepatotoxic prediction md: False
- ADMET EXT Hepatotoxic applicability: All properties and OPS components are within expected ranges.
- ADMET EXT Hepatotoxic applicability md: 8.77412
- ADMET EXT Hepatotoxic applicability mdpvalue: 0.571964
- ADMET Absorption Level: 0.0
- ADMET EXT PPB: -1.11858
- ADMET EXT PPB prediction: True
- ADMET EXT PPB applicability: All properties and OPS components are within expected ranges.
- ADMET EXT PPB applicability md: 9.45929
- ADMET EXT PPB applicability mdpvalue: 0.980424
- ADMET unknown AlogP98: 0.0
- ADMET AlogP98: 2.583
- ADMET PSA 2D: 20.815
2D/3D Properties
- Number of atoms: 11
- Molecular formula: C10H18O
- Molecular composition: C: 0.779, H: 0.118, O: 0.104
- Molecular mass: 154.136 g/mol
- Energy: 12.88 Kcal/M
- AlogP: 2.583
- LogD: 2.583
- Molecular Solubilty: -2.0140000000000002
- 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): 186.77 A^2
- Molecular SASA(Solvent accessible SA): 343.033 A^2
- Radius of gyration: 1.59604 A
- Molecular 3D SASA: 322.28700000000003 A^2
Consumption
- Consumption: 1166.67 lb
- Individual intake: 0.0009887 mg/kg/day
- Trade association guidelines: 36.585 mg
- IOFI: Nature Identical
Specifications
- Specifications: (JECFA, 2008); Appearance; Almost colorless, oily liquid with a ; spearmint-like odor; Refractive index; 1.4777–1.481 (20°C); Assay (min); 96%; Solubility; Soluble in alcohol and most fixed oils; ; insoluble in water; Boiling point; 225°C (d-isomer 222–223°C); Specific gravity; 0.921–0.926 (25°C)
Reported Uses
- Reported uses (ppm): (FEMA, 1994)
-
Food category usual/max:
Food category Usual (ppm) Max (ppm) Alcoholic beverages 3.45 8.76 Gelatins, puddings 78.00 90.00 Baked goods 162.00 185.40 Meat products 20.00 20.00 Chewing gum 5.47 5.47 Nonalcoholic beverages 55.55 65.07 Frozen dairy 177.40 194.40 Soft candy 132.30 162.80
Synthesis
- Synthesis: By reducing carvone and separating the resulting isomers
Physical-Chemical Characteristics
- Empirical formula / MW: C10H18O/154.24
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.