Linaloyl oxide
| Molecular & Flavor Profile | |
|---|---|
| Common name: | Linaloyl oxide |
| IUPAC name: | 2-ethenyl-2,6,6-trimethyloxane |
| SMILES: | CC1(CCCC(O1)(C)C=C)C |
| CAS: | 13837-56-4, 7392-19-0 |
| Flavor Profile: | Not Available |
| FEMA Flavor Profile: | Floral |
| FEMA Number: | 3735 |
| Taste: | Not Available |
| Odor: | Not Available |
| Functional Groups: | ether, dialkyl ether, alkene, heterocyclic compound |
External IDs
| PubChem ID: | 522514 |
|---|---|
| FooDB ID: | NA |
| SuperSweet ID: | NA |
| BitterDB ID: | NA |
Physicochemical Properties
- Molecular weight: 154.253 g/mol
- HBD count: 0
- HBA count: 1
- Number of rotatable bonds: 1
- Complexity: 160.0
- Topological Polor Surface Area: 9.2 A^2
- Monoisotopic Mass: 154.136 g/mol
- Exact Mass: 154.136 g/mol
- XlogP: 2.4
- 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/C10H18O/c1-5-10(4)8-6-7-9(2,3)11-10/h5H,1,6-8H2,2-4H3
- Volume 3D: 133.1
Nomenclature
- Common name: Linaloyl oxide
- IUPAC name: 2-ethenyl-2,6,6-trimethyloxane
- CAS numbers: 13837-56-4, 7392-19-0
- SMILES: CC1(CCCC(O1)(C)C=C)C
- InChI: InChI=1S/C10H18O/c1-5-10(4)8-6-7-9(2,3)11-10/h5H,1,6-8H2,2-4H3
- FlavorDB/FEMA name: 2,6,6-TRIMETHYL-6-VINYLTETRAHYDROPYRAN
- Synonyms: 2-Ethenyltetrahydro-2,6,6-trimethyl-2H-pyran; 2H-Pyran, 2-ethenyltetrahydro-2,6,6-trimethyl-; 2,6,6-Tri m ethoxy-2-vinyltetrahydropyran; 2,2,6-Trimethyl-6-vinyltetrahydropyran
- FL number: 13.094
- NAS number: 3735
- CoE number: 10976
- EINECS number: 230-983-3
- JECFA number: 1236
Description
- FEMA flavor profile: Floral
- Functional groups: ether, dialkyl ether, alkene, heterocyclic compound
- Bitter compound: No
- Source description: 2,6,6-Trimethyl-6-vinyltetrahydopyran has a musty, earthy, terpineolic odor
Regulatory Status
- JECFA status: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (2003)
Aroma/Taste Threshold Values
- Taste threshold values: Taste characteristics at 20 ppm; sweet, camphoraceous, woody and cooling with floral nuances
Natural Occurence
- Occurrence summary: Naturally occurring; Reported in 12 FlavorDB source entities
- Source entity count: 12
- Representative sources: White Wine, Black Tea, Buchu, Lime Peel Oil, Clary Sage, Cherimoya, Grape, Papaya, Passionfruit, Yellow Passionfruit
- Documented natural occurrence: Reported found in chestnut flower, muscat grapes and lime oil. Also reported found in grapefruit juice (Vitis labrusca L ) papaya (Carica papaya L ), white wine, black tea, purple passion fruit, yellow passion fruit, cherimoya, buchu oil, clary sage and loganberry
Composition
- Molecular formula: C10H18O
- Molecular composition: C: 0.779, H: 0.118, O: 0.104
- Number of atoms: 11
ADMET Properties
- ADMET Solubility: -3.096
- ADMET Solubility Level: 3.0
- ADMET BBB: 0.447
- ADMET BBB Level: 1.0
- ADMET EXT Hepatotoxic: -6.091069999999999
- ADMET EXT Hepatotoxic prediction md: False
- ADMET EXT Hepatotoxic applicability: All properties and OPS components are within expected ranges.
- ADMET EXT Hepatotoxic applicability md: 10.1497
- ADMET EXT Hepatotoxic applicability mdpvalue: 0.0644269
- ADMET Absorption Level: 0.0
- ADMET EXT PPB: -3.92391
- ADMET EXT PPB prediction: False
- ADMET EXT PPB applicability: All properties and OPS components are within expected ranges.
- ADMET EXT PPB applicability md: 11.4066
- ADMET EXT PPB applicability mdpvalue: 0.287596
- ADMET unknown AlogP98: 0.0
- ADMET AlogP98: 2.4
- ADMET PSA 2D: 8.93
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: 5.46 Kcal/M
- AlogP: 2.4
- LogD: 2.4
- Molecular Solubilty: -2.964
- 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: 1
- Surface area(SA): 202.92 A^2
- Molecular SASA(Solvent accessible SA): 338.156 A^2
- Radius of gyration: 1.51509 A
- Molecular 3D SASA: 314.725 A^2
Consumption
- Trade association guidelines: 0.043 mg
- IOFI: Nature Identical
Specifications
- Specifications: (JECFA, 2008); Acid value (max); 1.0; Refractive index; 1.446–1.452 (20°C); Appearance; Clear liquid; Solubility; Soluble in fat; insoluble in water; Assay (min); 99%; Specific gravity; 0.866–0.871 (25°C); Boiling point; 22°C (2.5 mmHg)
Reported Uses
- Reported uses (ppm): (FEMA, 1994)
-
Food category usual/max:
Food category Usual (ppm) Max (ppm) Confection, frosting 0.50 1.00 Nonalcoholic beverages 0.20 0.50 Gelatins, puddings 1.00 2.00 Soft candy 0.20 0.50
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.