Isopulegol
| Molecular & Flavor Profile | |
|---|---|
| Common name: | Isopulegol |
| IUPAC name: | (1R,2S,5R)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol |
| SMILES: | CC1CCC(C(C1)O)C(=C)C |
| CAS: | 89-79-2, 50373-36-9 |
| Flavor Profile: | cooling, minty, woody, medicinal |
| FEMA Flavor Profile: | Mint , Cool |
| FEMA Number: | 2962 |
| 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: 3
- 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/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
- Volume 3D: 133.0
Nomenclature
- Common name: Isopulegol
- IUPAC name: (1R,2S,5R)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
- CAS numbers: 89-79-2, 50373-36-9
- SMILES: CC1CCC(C(C1)O)C(=C)C
- InChI: InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
- FlavorDB/FEMA name: ISOPULEGOL
- Synonyms: p-Menth-8-en-3-ol; 1-Methyl-4-isopropenylcyclohexan-3-ol; Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R-(1alpha,2beta,5alpha))-; Isopulegol
- FL number: 2.067
- NAS number: 2962
- CoE number: 2033
- EINECS number: 201-940-6
- JECFA number: 755
Regulatory Status
- CoE status: 30 ppm
- FDA status: 21 CFR 172.515
- JECFA status: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (2000)
Aroma/Taste Threshold Values
- Aroma threshold values: 1 ppm
- Taste threshold values: Taste characteristics at 30 ppm; minty cooling, herbaceous peppermint nuance
Natural Occurence
- Occurrence summary: Naturally occurring; Reported in 22 FlavorDB source entities
- Source entity count: 22
- Representative sources: Cognac Brandy, Rum, Buchu, Citrus Peel Oil, Eucalyptus, Geranium, Lemon Grass, Mastic Gum, Currant, Black Currant
- Documented natural occurrence: l-Isopulegol has been reported found in the essences of lemongrass, East African geranium and Eucalyptus citriodora; d-isopulegol is present in the oils of Backhousia and Baeckea citriodorae; d-neoisopulegol is found in Mentha rotundifo-lia. Also reported found in mint, mandarin, orange juice, citrus peel oils, currant bud, ginger, corn mint oil, cognac, rum, buchu oil, lemon balm and mastic gum oil
Composition
- Molecular formula: C10H18O
- Molecular composition: C: 0.779, H: 0.118, O: 0.104
- Number of atoms: 11
ADMET Properties
- ADMET Solubility: -2.489
- ADMET Solubility Level: 3.0
- ADMET BBB: 0.315
- ADMET BBB Level: 1.0
- ADMET EXT Hepatotoxic: -7.31513
- 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: -1.3679700000000001
- 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: 11.49 Kcal/M
- AlogP: 2.583
- LogD: 2.583
- Molecular Solubilty: -2.035
- 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: 1.55344 A
- Molecular 3D SASA: 317.23900000000003 A^2
Consumption
- Consumption: 5016.00 lb
- Individual intake: 0.004251 mg/kg/day
- Trade association guidelines: 10.84 mg
- IOFI: Nature Identical
Specifications
- Specifications: (FCC, 1996); Acid value (max); 1.0; Optical rotation; Between 0° and –7°; Aldehydes; 1.0% as citronellal; Refractive index; 1.470–1.475 (25°C); Appearance; Colorless liquid; Solubility; 1:4 in 60% alcohol; Assay; 95% C10H18O; Specific gravity; 0.904–0.913 (25°C); Boiling point; 91° (12 mmHg)
Reported Uses
- Reported uses (ppm): (FEMA, 2005)
-
Food category usual/max:
Food category Usual (ppm) Max (ppm) Alcoholic beverages 50.00 200.00 Gelatins, puddings 50.00 200.00 Baked goods 14.00 19.00 Hard candy 100.00 500.00 Chewing gum 500.00 1000.00 Nonalcoholic beverages 50.00 200.00 Confectionery, frostings 100.00 500.00 Soft candy 100.00 500.00 Frozen dairy 12.00 15.00
Synthesis
- Synthesis: Several stereoisomers are possible; only l-isopulegol and d-α-isopulegol have been isolated from mixtures of alcohols obtained by cyclization of d-citronellal
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.