d-Piperitone
| Molecular & Flavor Profile | |
|---|---|
| Common name: | d-Piperitone |
| IUPAC name: | (6S)-3-methyl-6-propan-2-ylcyclohex-2-en-1-one |
| SMILES: | CC1=CC(=O)C(CC1)C(C)C |
| CAS: | 6091-50-5 |
| Flavor Profile: | minty, peppermint |
| FEMA Flavor Profile: | Mint , Cool |
| FEMA Number: | 2910 |
| Taste: | Not Available |
| Odor: | Not Available |
| Functional Groups: | carbonyl compound, ketone, alkene |
Physicochemical Properties
- Molecular weight: 152.237 g/mol
- HBD count: 0
- HBA count: 1
- Number of rotatable bonds: 1
- Complexity: 189.0
- Topological Polor Surface Area: 17.1 A^2
- Monoisotopic Mass: 152.12 g/mol
- Exact Mass: 152.12 g/mol
- XlogP: 2.2
- Charge: 0 C(coulomb)
- Heavy Atom Count: 11
- Atom Stereocenter Count: 1
- Defined Atom Stereocenter Count: 1
- Undefined Atom Stereocenter Count: 0
- 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/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3/t9-/m0/s1
- Volume 3D: 131.5
Nomenclature
- Common name: d-Piperitone
- IUPAC name: (6S)-3-methyl-6-propan-2-ylcyclohex-2-en-1-one
- CAS numbers: 6091-50-5
- SMILES: CC1=CC(=O)C(CC1)C(C)C
- InChI: InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3/t9-/m0/s1
- FlavorDB/FEMA name: d-PIPERITONE
- Synonyms: p-Menth-1-en-3-one; 4-Isopropyl-1-methyl-1-cyclohexen-3-one; 2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (S)-
- FL number: 7.175
- NAS number: 2910
- CoE number: 2052
- JECFA number: 435
Description
- Flavor profile: minty, peppermint
- FooDB flavor profile: minty, peppermint
- FEMA flavor profile: Mint, Cool
- Functional groups: carbonyl compound, ketone, alkene
- Bitter compound: No
- Source description: d-Piperitone has a camphor-like odor and a sharp, minty flavor
Regulatory Status
- CoE status: 40 ppm
- FDA status: 21 CFR 172.515
- 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: 680 ppb
Natural Occurence
- Occurrence summary: Naturally occurring; Reported in 26 FlavorDB source entities
- Source entity count: 26
- Representative sources: Buchu, Citrus Peel Oil, Eucalyptus, Lemon Peel Oil, Lime Peel Oil, Mastic Gum, Mentha Oil, Sweet Grass, Black Currant, Elderberry
- Documented natural occurrence: The structure has been defined by the work of several authors; the d-, l- and dl-forms are known; the d-form is found in the essential oils of Mentha silvestris, Cymbopogon sennaarensis and Japanese peppermint oil; the dl-form is found in the essential oils of Andropogon iwarancusa, Mentha pulegium var. hirsuta and in mixture with the l-form, Eucalyptus dives; the l-form, the most abundant, is found in about 30 varieties of eucalyptus and in other plants. It is also reported found in lemon and lime peel oil, lime juice, other citrus peel oils, black currants, raspberry, celery seed, cinnamon bark, peppermint oil, corn mint oil, other Mentha oils, nutmeg, pepper, mace, parsley seed oil, rose apple, starfruit, tamarind, elder flower, rosemary, buchu oil, lemon balm, sweet grass oil, eucalyptus oil and mastic gum fruit and leaf oil
Composition
- Molecular formula: C10H16O
- Molecular composition: C: 0.789, H: 0.106, O: 0.105
- Number of atoms: 11
ADMET Properties
- ADMET Solubility: -3.445
- ADMET Solubility Level: 3.0
- ADMET BBB: 0.47100000000000003
- ADMET BBB Level: 1.0
- ADMET EXT Hepatotoxic: -4.81032
- ADMET EXT Hepatotoxic prediction md: False
- ADMET EXT Hepatotoxic applicability: All properties and OPS components are within expected ranges.
- ADMET EXT Hepatotoxic applicability md: 7.55173
- ADMET EXT Hepatotoxic applicability mdpvalue: 0.9660709999999999
- ADMET Absorption Level: 0.0
- ADMET EXT PPB: -0.382367
- ADMET EXT PPB prediction: True
- ADMET EXT PPB applicability: All properties and OPS components are within expected ranges.
- ADMET EXT PPB applicability md: 8.81369
- ADMET EXT PPB applicability mdpvalue: 0.998616
- ADMET unknown AlogP98: 0.0
- ADMET AlogP98: 2.908
- ADMET PSA 2D: 17.3
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: 2.0 Kcal/M
- AlogP: 2.908
- LogD: 2.908
- Molecular Solubilty: -2.238
- 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): 185.22 A^2
- Molecular SASA(Solvent accessible SA): 339.36800000000005 A^2
- Radius of gyration: 1.65547 A
- Molecular 3D SASA: 321.219 A^2
Consumption
- Consumption: 183.33 lb
- Individual intake: 0.0001553 mg/kg/day
- Trade association guidelines: 3.376 mg
- IOFI: Nature Identical
Specifications
- Specifications: (JECFA, 2008); Appearance; Clear, light yellowish to yellow liquid; Refractive index; 1.483–1.487 (20°C); Assay (min); 94%; Solubility; Soluble in alcohol; insoluble in water; Boiling point; 233–235°C; Specific gravity; 0.929–0.934 (25°C)
Reported Uses
- Reported uses (ppm): (FEMA, 1994)
-
Food category usual/max:
Food category Usual (ppm) Max (ppm) Alcoholic beverages 3.94 8.02 Gelatins, puddings 4.06 8.27 Baked goods 19.55 39.07 Nonalcoholic beverages 2.02 4.15 Frozen dairy 6.18 12.36 Soft candy 19.74 39.45
Synthesis
- Synthesis: Isolated from Japanese mint oil; l-form from Eucalyptus dives oil; by hydrogenation of diosphenol; by reduction of 5-methyl-2-isopropylanisole with sodium in liquid NH4
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.