Sabinene hydrate
| Molecular & Flavor Profile | |
|---|---|
| Common name: | Sabinene hydrate |
| IUPAC name: | 4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-4-ol |
| SMILES: | CC(C)C12CCC(C1C2)(C)O |
| CAS: | 546-79-2 |
| Flavor Profile: | minty, eucalyptus, terpene, green |
| FEMA Flavor Profile: | Mint , Cool |
| FEMA Number: | 3239 |
| Taste: | Not Available |
| Odor: | Not Available |
| Functional Groups: | hydroxy compound, alcohol, tertiary alcohol |
Physicochemical Properties
- Molecular weight: 154.253 g/mol
- HBD count: 1
- HBA count: 1
- Number of rotatable bonds: 1
- Complexity: 187.0
- Topological Polor Surface Area: 20.2 A^2
- Monoisotopic Mass: 154.136 g/mol
- Exact Mass: 154.136 g/mol
- XlogP: 2.1
- 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)10-5-4-9(3,11)8(10)6-10/h7-8,11H,4-6H2,1-3H3
- Volume 3D: 132.3
Nomenclature
- Common name: Sabinene hydrate
- IUPAC name: 4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-4-ol
- CAS numbers: 546-79-2
- SMILES: CC(C)C12CCC(C1C2)(C)O
- InChI: InChI=1S/C10H18O/c1-7(2)10-5-4-9(3,11)8(10)6-10/h7-8,11H,4-6H2,1-3H3
- FlavorDB/FEMA name: THUJAN-4-OL
- Synonyms: Bicyclo(3 1 0)hexan-2-ol, 2-methyl-5-(1-methylethyl)-; 2-Methyl-5-(1-methylethyl)bicyclo(3 1 0)hexan-2-ol; Sabinene hydrate; 4-Thujanol
- FL number: 2.085
- NAS number: 3239
- CoE number: 10309
- EINECS number: 208-911-7
- JECFA number: 441
Description
- Flavor profile: minty, eucalyptus, terpene, green
- FooDB flavor profile: minty, eucalyptus, terpene, green
- FEMA flavor profile: Mint, Cool
- Functional groups: hydroxy compound, alcohol, tertiary alcohol
- Bitter compound: No
- Source description: Thujan-4-ol has an odor reminiscent of terpineol
Regulatory Status
- JECFA status: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (1995)
Aroma/Taste Threshold Values
- Aroma threshold values: Aroma characteristics at 1.0%; earthy camphoreous pine and turpentine-like with citrus grapefruit nuances
- Taste threshold values: Taste characteristics at 5 ppm; woody, citrus orange and grapefruit-like
Natural Occurence
- Occurrence summary: Naturally occurring; Reported in 23 FlavorDB source entities
- Source entity count: 23
- Representative sources: Mandarin Orange Peel Oil, Mentha Oil, Black Currant, Lemon, Mandarin Orange, Basil, Cornmint, Dill, Rosemary, Spearmint
- Documented natural occurrence: Reported found in peppermint oil (trans-form), lemon juice, mandarin peel oil, mandarin, nutmeg, peppermint, rosemary, scotch spearmint, tarragon, thyme, black currant (buds), Vitis vinifera L , ginger, spearmint oil, other Mentha oils, pepper, sweet marjoram, cardamom, origanum, dill herb, Oscimum basilicum varieties and laurel
Composition
- Molecular formula: C10H18O
- Molecular composition: C: 0.779, H: 0.118, O: 0.104
- Number of atoms: 11
ADMET Properties
- ADMET Solubility: -2.207
- ADMET Solubility Level: 3.0
- ADMET BBB: 0.106
- ADMET BBB Level: 1.0
- ADMET EXT Hepatotoxic: -2.80998
- ADMET EXT Hepatotoxic prediction md: True
- ADMET EXT Hepatotoxic applicability: All properties and OPS components are within expected ranges.
- ADMET EXT Hepatotoxic applicability md: 7.473660000000001
- ADMET EXT Hepatotoxic applicability mdpvalue: 0.973557
- ADMET Absorption Level: 0.0
- ADMET EXT PPB: -3.20424
- ADMET EXT PPB prediction: False
- ADMET EXT PPB applicability: All properties and OPS components are within expected ranges.
- ADMET EXT PPB applicability md: 6.952030000000001
- ADMET EXT PPB applicability mdpvalue: 1.0
- ADMET unknown AlogP98: 0.0
- ADMET AlogP98: 1.906
- 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: 62.91 Kcal/M
- AlogP: 1.906
- LogD: 1.906
- Molecular Solubilty: -2.22
- 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: 2
- Surface area(SA): 184.03 A^2
- Molecular SASA(Solvent accessible SA): 310.32099999999997 A^2
- Radius of gyration: 1.5402200000000001 A
- Molecular 3D SASA: 313.149 A^2
Consumption
- Consumption: <1.00 lb
- Individual intake: 0.00000007 mg/kg/day
- Trade association guidelines: 1.498 mg
- IOFI: Natural
Specifications
- Specifications: (JECFA, 1998); Assay (min); 98%; Refractive index; 1.443–1.449 (60°C); Boiling point; 193–196°C (trans); 195–200°C (cis)
Reported Uses
- Reported uses (ppm): (FEMA, 1994)
-
Food category usual/max:
Food category Usual (ppm) Max (ppm) Alcoholic beverages 2.00 4.00 Gelatins, puddings 4.00 8.00 Baked goods 8.00 16.00 Nonalcoholic beverages 1.00 2.00 Frozen dairy 4.07 8.14 Soft candy 7.79 15.58
Synthesis
- Synthesis: The Grignard reaction with sabina ketone yields two isomers, of which one is identical to an alcohol isolated from American peppermint oil; synthetic routes for the preparation of both the cis- and trans-form are also available
Physical-Chemical Characteristics
- Empirical formula / MW: C10H18O/154.25
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.