trans-2-Hexenyl butyrate
| Molecular & Flavor Profile | |
|---|---|
| Common name: | trans-2-Hexenyl butyrate |
| IUPAC name: | [(E)-hex-2-enyl] butanoate |
| SMILES: | CCCC=CCOC(=O)CCC |
| CAS: | 53398-83-7 |
| Flavor Profile: | apple, banana, fruity, orchid, grassy, green |
| FEMA Flavor Profile: | Fruit |
| FEMA Number: | 3926 |
| Taste: | Not Available |
| Odor: | Not Available |
| Functional Groups: | carboxylic acid derivative, carboxylic acid ester, alkene |
Physicochemical Properties
- Molecular weight: 170.252 g/mol
- HBD count: 0
- HBA count: 2
- Number of rotatable bonds: 7
- Complexity: 139.0
- Topological Polor Surface Area: 26.3 A^2
- Monoisotopic Mass: 170.131 g/mol
- Exact Mass: 170.131 g/mol
- XlogP: 2.8
- Charge: 0 C(coulomb)
- Heavy Atom Count: 12
- Atom Stereocenter Count: 0
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Bond Stereocenter Count: 1
- Defined Bond Stereocenter Count: 1
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently Bonded Unit Count: 1
- InChI: InChI=1S/C10H18O2/c1-3-5-6-7-9-12-10(11)8-4-2/h6-7H,3-5,8-9H2,1-2H3/b7-6+
- Volume 3D: 149.3
Nomenclature
- Common name: trans-2-Hexenyl butyrate
- IUPAC name: [(E)-hex-2-enyl] butanoate
- CAS numbers: 53398-83-7
- SMILES: CCCC=CCOC(=O)CCC
- InChI: InChI=1S/C10H18O2/c1-3-5-6-7-9-12-10(11)8-4-2/h6-7H,3-5,8-9H2,1-2H3/b7-6+
- FlavorDB/FEMA name: (E)-2-HEXENYL BUTYRATE
- Synonyms: Butanoic acid, 2-hexenyl ester; trans-2-Hexenyl butanoate; trans-2-Hexenyl butyrate; Butanoic acid, (2E)-2-hexen-1-yl ester
- FL number: 9.369
- NAS number: 8773
- EINECS number: 258-515-3
- JECFA number: 1375
Description
- Flavor profile: apple, banana, fruity, orchid, grassy, green
- FooDB flavor profile: apple, banana, fruity, orchid, grassy, green
- FEMA flavor profile: Fruit
- Functional groups: carboxylic acid derivative, carboxylic acid ester, alkene
- Bitter compound: No
- Source description: (E)-2-Hexenyl butyrate has a green, fruity odor
Regulatory Status
- JECFA status: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (2004)
Aroma/Taste Threshold Values
- Aroma threshold values: Aroma characteristics at 1.0%; green, ripe fruity with apple and fermented banana notes and a fatty nuance, becoming green grassy on dryout
- Taste threshold values: Taste characteristics at 1 to 10 ppm; green, oily, fresh fruity with a full mouthfeel
Natural Occurence
- Occurrence summary: Naturally occurring; Reported in 8 FlavorDB source entities
- Source entity count: 8
- Representative sources: Black Tea, Lovage, Cherimoya, Plum, Blueberry, Cranberry, Strawberry, Chicken
- Documented natural occurrence: Reported found in high bush cranberry, strawberry, chicken fat, black tea, fresh plum, lovage root and chermoya fruit
Composition
- Molecular formula: C10H18O2
- Molecular composition: C: 0.705, H: 0.107, O: 0.188
- Number of atoms: 12
ADMET Properties
- ADMET Solubility: -2.785
- ADMET Solubility Level: 3.0
- ADMET BBB: 0.381
- ADMET BBB Level: 1.0
- ADMET EXT Hepatotoxic: -12.3215
- ADMET EXT Hepatotoxic prediction md: False
- ADMET EXT Hepatotoxic applicability: All properties and OPS components are within expected ranges.
- ADMET EXT Hepatotoxic applicability md: 9.11246
- ADMET EXT Hepatotoxic applicability mdpvalue: 0.401096
- ADMET Absorption Level: 0.0
- ADMET EXT PPB: -3.0529599999999997
- ADMET EXT PPB prediction: False
- ADMET EXT PPB applicability: All properties and OPS components are within expected ranges.
- ADMET EXT PPB applicability md: 9.66874
- ADMET EXT PPB applicability mdpvalue: 0.961461
- ADMET unknown AlogP98: 0.0
- ADMET AlogP98: 3.075
- 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: 2.53 Kcal/M
- AlogP: 3.075
- LogD: 3.075
- Molecular Solubilty: -2.878
- 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: 0
- Surface area(SA): 217.24 A^2
- Molecular SASA(Solvent accessible SA): 397.086 A^2
- Radius of gyration: 1.765 A
- Molecular 3D SASA: 366.13599999999997 A^2
Consumption
- Trade association guidelines: 2.176 mg
- IOFI: Nature Identical
Specifications
- Specifications: (JECFA, 2008); Acid value (max); 2.0; Refractive index; 1.429–1.435 (20°C); Appearance; Colorless liquid; Solubility; Insoluble in water; soluble in alcohol; Assay (min); 95%; Specific gravity; 0.882–0.888 (25°C); Boiling point; 190°C
Reported Uses
- Reported uses (ppm): (FEMA, 2000)
-
Food category usual/max:
Food category Usual (ppm) Max (ppm) Alcoholic beverages 5.00 10.00 Imitation dairy 5.00 5.00 Baked goods 7.20 40.00 Jams, jellies 0.50 1.00 Chewing gum 20.00 50.00 Milk products 5.00 20.00 Confection, frosting 10.00 20.00 Nonalcoholic beverages 5.00 10.00 Frozen dairy 5.00 20.00 Soft candy 10.00 20.00 Gelatins, puddings 5.00 20.00 Sweet sauce 0.50 1.00 Hard candy 10.00 20.00
Physical-Chemical Characteristics
- Empirical formula / MW: C10H18O2/170.25CH3OCH3O
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.