16491-36-4
| Molecular & Flavor Profile | |
|---|---|
| Common name: | 16491-36-4 |
| IUPAC name: | [(Z)-hex-3-enyl] butanoate |
| SMILES: | CCCC(=O)OCCC=CCC |
| CAS: | 16491-36-4 |
| Flavor Profile: | apple, wine, fresh, fruity, metallic, buttery, green |
| FEMA Flavor Profile: | Not Available |
| FEMA Number: | 3402 |
| 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: 2.7
- 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/h5-6H,3-4,7-9H2,1-2H3/b6-5-
- Volume 3D: 148.3
Nomenclature
- Common name: 16491-36-4
- IUPAC name: [(Z)-hex-3-enyl] butanoate
- CAS numbers: 16491-36-4
- SMILES: CCCC(=O)OCCC=CCC
- InChI: InChI=1S/C10H18O2/c1-3-5-6-7-9-12-10(11)8-4-2/h5-6H,3-4,7-9H2,1-2H3/b6-5-
- FlavorDB/FEMA name: cis-3-HEXENYL BUTYRATE
- Synonyms: β,γ-Hexenyl-n-butyrate; cis-3-Hexenyl butanoate; Leaf butyrate; Butanoic acid, 3-hexenyl ester, (Z)-; cis-Butyric acid, 3-hexenyl ester; (Z)-3-Hexenyl butanoate; cis-3-Hexenyl butyrate; cis-3-Hexen-1-yl butyrate; (Z)-Hex-3-enyl butyrate; Butanoic acid, (3Z)-3-hexen-1-yl ester
- FL number: 9.27
- NAS number: 3402
- CoE number: 11859
- EINECS number: 240-553-7
- JECFA number: 157
Description
- Flavor profile: apple, wine, fresh, fruity, metallic, buttery, green
- FooDB flavor profile: apple, wine, fresh, fruity, metallic, buttery, green
- Functional groups: carboxylic acid derivative, carboxylic acid ester, alkene
- Bitter compound: No
- Source description: cis-3-Hexenyl butyrate has a green, fruity, somewhat buttery aroma
Regulatory Status
- 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: green, waxy, fruity and sweet with a berry and tropical nuance
- Taste threshold values: Taste characteristics at 20 ppm; green, fruity, leafy with a fresh apple and pear nuance
Natural Occurence
- Occurrence summary: Naturally occurring; Reported in 20 FlavorDB source entities
- Source entity count: 20
- Representative sources: Lemon Peel Oil, Lovage, Apple, Apricot, Grape, Guava, Mango, Orange, Passionfruit, Peach
- Documented natural occurrence: Reported found in passion fruit, apricot, orange and lemon peel oil, apple, Concord grape, guava, strawberry, tea, plum, plumcot, starfruit, mango, coriander, quince, lovage, nectarine and spineless monkey orange
Composition
- Molecular formula: C10H18O2
- Molecular composition: C: 0.705, H: 0.107, O: 0.188
- Number of atoms: 12
ADMET Properties
- ADMET Solubility: -2.667
- ADMET Solubility Level: 3.0
- ADMET BBB: 0.34
- ADMET BBB Level: 1.0
- ADMET EXT Hepatotoxic: -12.1536
- ADMET EXT Hepatotoxic prediction md: False
- ADMET EXT Hepatotoxic applicability: All properties and OPS components are within expected ranges.
- ADMET EXT Hepatotoxic applicability md: 7.77376
- ADMET EXT Hepatotoxic applicability mdpvalue: 0.9353319999999999
- ADMET Absorption Level: 0.0
- ADMET EXT PPB: -1.27972
- ADMET EXT PPB prediction: True
- ADMET EXT PPB applicability: All properties and OPS components are within expected ranges.
- ADMET EXT PPB applicability md: 8.41431
- ADMET EXT PPB applicability mdpvalue: 0.9998309999999999
- ADMET unknown AlogP98: 0.0
- ADMET AlogP98: 2.94
- 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: 3.72 Kcal/M
- AlogP: 2.94
- LogD: 2.94
- Molecular Solubilty: -2.826
- 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: 2.00299 A
- Molecular 3D SASA: 370.259 A^2
Consumption
- Consumption: 91.67 lb
- Individual intake: 0.00007768 mg/kg/day
- Trade association guidelines: 0.415 mg
- IOFI: Nature Identical
Specifications
- Specifications: (JECFA, 1997); Appearance; Colorless to pale-yellow liquid; Refractive index; 1.420–1.435 (20°C); Assay (min); 95%; Solubility; Soluble in alcohol and propylene ; glycol; miscible with most oils; ; insoluble in water; Boiling point; 192°C; Specific gravity; 0.860–0.899 (25°C)
Reported Uses
- Reported uses (ppm): (FEMA, 1994)
-
Food category usual/max:
Food category Usual (ppm) Max (ppm) Alcoholic beverages 0.10 0.50 Gelatins, puddings 1.10 3.00 Baked goods 1.30 2.60 Hard candy 1.00 15.00 Breakfast cereals 7.00 14.00 Jams, jellies 1.30 2.60 Chewing gum 0.16 0.25 Nonalcoholic beverages 0.30 2.00 Confectionary, frosting 1.20 2.40 Soft candy 1.00 15.00 Frozen dairy 1.00 5.00
Synthesis
- Synthesis: By esterification of cis-3-hexenol with n-butyric acid under azeotropic conditions
Physical-Chemical Characteristics
- Empirical formula / MW: C10H18O2/170.25
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.