Delta-Decalactone
| Molecular & Flavor Profile | |
|---|---|
| Common name: | Delta-Decalactone |
| IUPAC name: | 6-pentyloxan-2-one |
| SMILES: | CCCCCC1CCCC(=O)O1 |
| CAS: | 705-86-2 |
| Flavor Profile: | peach, butter, coconut, apricot, fresh, oily, creamy, plum, sweet, fruity, dairy |
| FEMA Flavor Profile: | Coconut |
| FEMA Number: | 2361 |
| Taste: | Not Available |
| Odor: | Not Available |
| Functional Groups: | carboxylic acid derivative, carboxylic acid ester, lactone, heterocyclic compound |
Physicochemical Properties
- Molecular weight: 170.252 g/mol
- HBD count: 0
- HBA count: 2
- Number of rotatable bonds: 4
- Complexity: 143.0
- Topological Polor Surface Area: 26.3 A^2
- Monoisotopic Mass: 170.131 g/mol
- Exact Mass: 170.131 g/mol
- XlogP: 2.5
- Charge: 0 C(coulomb)
- Heavy Atom Count: 12
- 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/C10H18O2/c1-2-3-4-6-9-7-5-8-10(11)12-9/h9H,2-8H2,1H3
- Volume 3D: 143.9
Nomenclature
- Common name: Delta-Decalactone
- IUPAC name: 6-pentyloxan-2-one
- CAS numbers: 705-86-2
- SMILES: CCCCCC1CCCC(=O)O1
- InChI: InChI=1S/C10H18O2/c1-2-3-4-6-9-7-5-8-10(11)12-9/h9H,2-8H2,1H3
- FlavorDB/FEMA name: δ-DECALACTONE
- Synonyms: delta-Decalactone; Decanolide-1,4; γ-n-Butyrolactone; 5-Hydroxy-decanoic acid,. δ-lactone; delta-Dodecalactone; Dodecanoic acid, 5-hydroxy-, delta-lactone; Dodecan-5-olide; Amyl-delta-valerolactone; Decan-5-olide; 2H-Pyran-2-one, 6-pen-tyl; Tetrahydro-6-pentyl-2H-pyran-2-one
- FL number: 10.007
- NAS number: 2361
- CoE number: 621
- EINECS number: 211-889-1
- JECFA number: 232
Description
- Flavor profile: peach, butter, coconut, apricot, fresh, oily, creamy, plum, sweet, fruity, dairy
- FooDB flavor profile: peach, butter, coconut, apricot, fresh, oily, creamy, plum, sweet, fruity, dairy
- FEMA flavor profile: Coconut
- Functional groups: carboxylic acid derivative, carboxylic acid ester, lactone, heterocyclic compound
- Bitter compound: No
- Source description: δ-Decalactone has an oily, peach odor and taste
Regulatory Status
- CoE status: 20 ppm
- FDA status: 21 CFR 172.515
- JECFA status: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (1997)
Aroma/Taste Threshold Values
- Aroma threshold values: 100 ppb
- Taste threshold values: Taste characteristics at 2 ppm; waxy, coconut, lactonic, fatty, creamy, nutty and fruity
Natural Occurence
- Occurrence summary: Naturally occurring; Reported in 14 FlavorDB source entities
- Source entity count: 14
- Representative sources: Rum, Butter, Other Cheeses, Swiss Cheese, Milk, Milk Powder, Apricot, Coconut, Mango, Peach
- Documented natural occurrence: Reported found in rum, coconut, raspberry, apricot, bilberry, peach, strawberry, Swiss cheese, other cheeses, butter, milk, milk powder, mutton fat, mango and nectarine
Composition
- Molecular formula: C10H18O2
- Molecular composition: C: 0.705, H: 0.107, O: 0.188
- Number of atoms: 12
ADMET Properties
- ADMET Solubility: -3.205
- ADMET Solubility Level: 3.0
- ADMET BBB: 0.359
- ADMET BBB Level: 1.0
- ADMET EXT Hepatotoxic: -18.8384
- ADMET EXT Hepatotoxic prediction md: False
- ADMET EXT Hepatotoxic applicability: All properties and OPS components are within expected ranges.
- ADMET EXT Hepatotoxic applicability md: 7.35815
- ADMET EXT Hepatotoxic applicability mdpvalue: 0.9821200000000001
- ADMET Absorption Level: 0.0
- ADMET EXT PPB: 0.580242
- ADMET EXT PPB prediction: True
- ADMET EXT PPB applicability: All properties and OPS components are within expected ranges.
- ADMET EXT PPB applicability md: 10.7702
- ADMET EXT PPB applicability mdpvalue: 0.606162
- ADMET unknown AlogP98: 0.0
- ADMET AlogP98: 3.002
- ADMET PSA 2D: 26.23
2D/3D Properties
- Number of atoms: 12
- Molecular formula: C10H18O2
- Molecular composition: C: 0.705, H: 0.107, O: 0.188
- Molecular mass: 170.13099999999997 g/mol
- Energy: 13.33 Kcal/M
- AlogP: 3.002
- LogD: 3.002
- Molecular Solubilty: -2.662
- Number of aromatic bonds: 0
- Number of aromatic rings: 0
- Number of H acceptor: 2
- Number of H acceptor lipinski: 2
- Number of H donor: 0
- Number of H donor lipinski: 0
- Number of H bonds: 0
- Number of rings: 1
- Surface area(SA): 196.22 A^2
- Molecular SASA(Solvent accessible SA): 379.74699999999996 A^2
- Radius of gyration: 1.61642 A
- Molecular 3D SASA: 338.47900000000004 A^2
Consumption
- Consumption: 36166.67 lb
- Individual intake: 0.03064 mg/kg/day
- Trade association guidelines: 3.556 mg
- IOFI: Natural
Specifications
- Specifications: (JECFA, 1998); Acid value (max); 5.0; Boiling point; 281°C; Appearance; Colorless liquid; Refractive index; 1.456–1.459 (20°C); Assay (min); 98%; Solubility; Very soluble in alcohol and propylene ; glycol; insoluble in water
Reported Uses
- Reported uses (ppm): (FEMA, 1994)
-
Food category usual/max:
Food category Usual (ppm) Max (ppm) Alcoholic beverages 3.00 6.50 Gelatins, puddings 14.64 29.62 Baked goods 13.52 26.40 Gravies 4.00 8.00 Confection, frosting 0.50 5.00 Nonalcoholic beverages 5.33 13.69 Fats, oils 9.06 19.70 Soft candy 13.27 25.63 Frozen dairy 18.78 37.06 Sweet sauce 0.13 0.13
Synthesis
- Synthesis: From hexylethylene oxide and sodium malonic ester; also from decanoic acid
Physical-Chemical Characteristics
- Empirical formula / MW: C10H18O2/170.25CH3OO
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.