Phenoxyacetic Acid
| Molecular & Flavor Profile | |
|---|---|
| Common name: | Phenoxyacetic Acid |
| IUPAC name: | 2-phenoxyacetic acid |
| SMILES: | C1=CC=C(C=C1)OCC(=O)O |
| CAS: | 122-59-8 |
| Flavor Profile: | sour, sweet |
| FEMA Flavor Profile: | Not Available |
| FEMA Number: | 2872 |
| Taste: | Not Available |
| Odor: | Not Available |
| Functional Groups: | ether, alkyl aryl ether, carboxylic acid derivative, carboxylic acid, aromatic compound |
Physicochemical Properties
- Molecular weight: 152.149 g/mol
- HBD count: 1
- HBA count: 3
- Number of rotatable bonds: 3
- Complexity: 127.0
- Topological Polor Surface Area: 46.5 A^2
- Monoisotopic Mass: 152.047 g/mol
- Exact Mass: 152.047 g/mol
- XlogP: 1.3
- 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/C8H8O3/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
- Volume 3D: 119.6
Nomenclature
- Common name: Phenoxyacetic Acid
- IUPAC name: 2-phenoxyacetic acid
- CAS numbers: 122-59-8
- SMILES: C1=CC=C(C=C1)OCC(=O)O
- InChI: InChI=1S/C8H8O3/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
- FlavorDB/FEMA name: PHENOXYACETIC ACID
- Synonyms: Glycolic acid phenyl ether; Phenoxyethanoic acid; o-Phenylglycolic acid; Phenylium; Acetic acid, phenoxy-; Glycolic acid, phenyl ether; Glycollic acid phenyl ether; Phenoxyacetic acid; POA
- FL number: 8.049
- NAS number: 2872
- CoE number: 2005
- EINECS number: 204-556-7
- JECFA number: 1026
Description
- Flavor profile: sour, sweet
- FooDB flavor profile: sour, sweet
- Functional groups: ether, alkyl aryl ether, carboxylic acid derivative, carboxylic acid, aromatic compound
- Bitter compound: No
- Source description: Phenoxyacetic acid has a sour, sweet odor and a honey-like taste
Regulatory Status
- CoE status: Grouped under phenyl ethyl alcohols, phenylacetic acids, related esters, phenoxyacetic acids and related esters
- FDA status: 21 CFR 172.515
- JECFA status: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (2002)
Natural Occurence
- Occurrence summary: Naturally occurring; Reported in 1 FlavorDB source entity
- Source entity count: 1
- Representative sources: Cocoa
- Documented natural occurrence: Reported found in cocoa beans
Composition
- Molecular formula: C8H8O3
- Molecular composition: C: 0.632, H: 0.053, O: 0.315
- Number of atoms: 11
ADMET Properties
- ADMET Solubility: -1.306
- ADMET Solubility Level: 4.0
- ADMET BBB: -0.498
- ADMET BBB Level: 2.0
- ADMET EXT Hepatotoxic: -3.9525300000000003
- ADMET EXT Hepatotoxic prediction md: True
- ADMET EXT Hepatotoxic applicability: All properties and OPS components are within expected ranges.
- ADMET EXT Hepatotoxic applicability md: 10.5214
- ADMET EXT Hepatotoxic applicability mdpvalue: 0.025354400000000003
- ADMET Absorption Level: 0.0
- ADMET EXT PPB: -1.6336600000000001
- ADMET EXT PPB prediction: True
- ADMET EXT PPB applicability: All properties and OPS components are within expected ranges.
- ADMET EXT PPB applicability md: 9.3728
- ADMET EXT PPB applicability mdpvalue: 0.9855649999999999
- ADMET unknown AlogP98: 0.0
- ADMET AlogP98: 1.295
- ADMET PSA 2D: 47.04600000000001
2D/3D Properties
- Number of atoms: 11
- Molecular formula: C8H8O3
- Molecular composition: C: 0.632, H: 0.053, O: 0.315
- Molecular mass: 152.047 g/mol
- Energy: 16.29 Kcal/M
- AlogP: 1.295
- LogD: -0.179
- Molecular Solubilty: -1.475
- pKa: 2.91
- Number of aromatic bonds: 6
- Number of aromatic rings: 1
- Number of H acceptor: 3
- Number of H acceptor lipinski: 3
- Number of H donor: 1
- Number of H donor lipinski: 1
- Number of H bonds: 0
- Number of rings: 1
- Surface area(SA): 158.95 A^2
- Molecular SASA(Solvent accessible SA): 324.13 A^2
- Radius of gyration: 1.91766 A
- Molecular 3D SASA: 304.496 A^2
Consumption
- Consumption: 1.67 lb
- Individual intake: 0.00000141 mg/kg/day
- Trade association guidelines: 0.545 mg
- IOFI: Artificial
Specifications
- Specifications: (JECFA, 2008); Appearance; Colorless needle-like crystals; Melting point; 98–103°C; Assay (min); 98%; Solubility; Slightly soluble in water; soluble in ; alcohol at room temperature, soluble ; in oils; Boiling point; 285°C (decomposes)
Reported Uses
- Reported uses (ppm): (FEMA, 1994)
-
Food category usual/max:
Food category Usual (ppm) Max (ppm) Alcoholic beverages 0.88 1.50 Gelatins, puddings 1.00 2.00 Baked goods 2.88 5.64 Nonalcoholic beverages 0.45 1.25 Frozen dairy 1.38 2.75 Soft candy 3.25 6.00
Synthesis
- Synthesis: By reacting phenol and monochloroacetic acid
Physical-Chemical Characteristics
- Empirical formula / MW: C8H8O3/152.15
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.