beta-Cyclocitral
| Molecular & Flavor Profile | |
|---|---|
| Common name: | beta-Cyclocitral |
| IUPAC name: | 2,6,6-trimethylcyclohexene-1-carbaldehyde |
| SMILES: | CC1=C(C(CCC1)(C)C)C=O |
| CAS: | 52844-21-0, 432-25-7 |
| Flavor Profile: | mint, saffron, tobacco, herbal, damascone, sweet, tropical, clean, fruity, rose oxide, minty |
| FEMA Flavor Profile: | Not Available |
| FEMA Number: | 3639 |
| Taste: | Not Available |
| Odor: | Not Available |
| Functional Groups: | carbonyl compound, aldehyde, alkene |
Physicochemical Properties
- Molecular weight: 152.237 g/mol
- HBD count: 0
- HBA count: 1
- Number of rotatable bonds: 1
- Complexity: 199.0
- Topological Polor Surface Area: 17.1 A^2
- Monoisotopic Mass: 152.12 g/mol
- Exact Mass: 152.12 g/mol
- XlogP: 2.4
- Charge: 0 C(coulomb)
- Heavy Atom Count: 11
- Atom Stereocenter Count: 0
- Defined Atom Stereocenter Count: 0
- 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/c1-8-5-4-6-10(2,3)9(8)7-11/h7H,4-6H2,1-3H3
- Volume 3D: 130.1
Nomenclature
- Common name: beta-Cyclocitral
- IUPAC name: 2,6,6-trimethylcyclohexene-1-carbaldehyde
- CAS numbers: 52844-21-0, 432-25-7
- SMILES: CC1=C(C(CCC1)(C)C)C=O
- InChI: InChI=1S/C10H16O/c1-8-5-4-6-10(2,3)9(8)7-11/h7H,4-6H2,1-3H3
- FlavorDB/FEMA name: 2,6,6-TRIMETHYL-1,2-CYCLOHEXEN-1-CARBOXALDEHYDE
- Synonyms: α,β-cyclocitral (50/50 mixture)
- FL number: 5.182
- NAS number: 3639
- CoE number: 2133
- EINECS number: 207-081-3
- JECFA number: 979
Description
- Flavor profile: mint, saffron, tobacco, herbal, damascone, sweet, tropical, clean, fruity, rose oxide, minty
- FooDB flavor profile: mint, saffron, tobacco, herbal, damascone, sweet, tropical, clean, fruity, rose oxide, minty
- Functional groups: carbonyl compound, aldehyde, alkene
- Bitter compound: No
- Source description: 2,6,6-Trimethyl-1,2-cyclohexen-1-carboxaldehyde has a camphoraceous odor for a 50/50 mixture of isomers
Regulatory Status
- JECFA status: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (2003)
- EAFUS number: 977045-71-8
Natural Occurence
- Occurrence summary: Naturally occurring; Reported in 23 FlavorDB source entities
- Source entity count: 23
- Representative sources: Apple Brandy, Rum, Mate, Oats, Apricot, Fig, Loquat, Mango, Melon, Plumcot
- Documented natural occurrence: Reported found in tea, apricot, melon, tomato, tomato paste, ginger, rum, Japanese plum, plumcot, mango, apple brandy, calamus, buckwheat, Bourbon vanilla, cape gooseberry and maté
Composition
- Molecular formula: C10H16O
- Molecular composition: C: 0.789, H: 0.106, O: 0.105
- Number of atoms: 11
ADMET Properties
- ADMET Solubility: -3.409
- ADMET Solubility Level: 3.0
- ADMET BBB: 0.44
- ADMET BBB Level: 1.0
- ADMET EXT Hepatotoxic: -6.52473
- ADMET EXT Hepatotoxic prediction md: False
- ADMET EXT Hepatotoxic applicability: All properties and OPS components are within expected ranges.
- ADMET EXT Hepatotoxic applicability md: 9.020710000000001
- ADMET EXT Hepatotoxic applicability mdpvalue: 0.44657600000000003
- ADMET Absorption Level: 0.0
- ADMET EXT PPB: 2.77025
- ADMET EXT PPB prediction: True
- ADMET EXT PPB applicability: All properties and OPS components are within expected ranges.
- ADMET EXT PPB applicability md: 8.68267
- ADMET EXT PPB applicability mdpvalue: 0.9992770000000001
- ADMET unknown AlogP98: 0.0
- ADMET AlogP98: 2.8080000000000003
- 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: 3.68 Kcal/M
- AlogP: 2.8080000000000003
- LogD: 2.8080000000000003
- Molecular Solubilty: -2.529
- 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): 195.23 A^2
- Molecular SASA(Solvent accessible SA): 337.12199999999996 A^2
- Radius of gyration: 1.46909 A
- Molecular 3D SASA: 303.822 A^2
Consumption
- Consumption: <1.00 lb
- Individual intake: 0.00000026 mg/kg/day
- Trade association guidelines: 0.001 mg
Specifications
- Specifications: (JECFA, 2008); Appearance; Colorless liquid; Refractive index; 1.476–1.483 (20°C); Assay (min); 99%; Solubility; Insoluble in water; Boiling point; 62°C (3 mmHg); Specific gravity; 0.950–0.957 (25°C); Other requirements; Approx. 50% α-cyclocitral and 50% ; β-cyclocitral
Reported Uses
- Reported uses (ppm): (FEMA, 1994)
-
Food category usual/max:
Food category Usual (ppm) Max (ppm) Baked goods 0.006 0.06 Hard candy 0.01 0.10 Chewing gum 0.05 0.50 Jams, jellies 0.005 0.05 Confection, frosting 0.005 0.05 Nonalcoholic beverages 0.002 0.02 Fruit ices 0.01 0.10 Soft candy 0.005 0.05 Gelatins, puddings 0.005 0.05
Physical-Chemical Characteristics
- Empirical formula / MW: C10H16O/152.23
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.