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phenyl pyruvic acid
Phenyl Pyruvic Acid is an aromatic alpha-keto acid with a honey-like odor and phenolic flavor, used as a flavor and fragrance agent.
General Material Description
Phenyl Pyruvic Acid, systematically known as 2-oxo-3-phenylpropionic acid, is an aromatic alpha-keto acid with the molecular formula C9H8O3. Its structure features a keto group adjacent to a phenyl-substituted propanoic acid backbone. This compound is recognized for its characteristic honey-like odor with medium intensity and a phenolic, grassy flavor profile. It appears as a solid at room temperature and is soluble in alcohol, water, and propylene glycol. Phenyl Pyruvic Acid occurs both naturally and synthetically, and it has various synonyms, including alpha-oxo-benzenepropanoic acid and 3-phenyl-2-oxopropanoic acid. For detailed chemical information, it is listed in authoritative sources such as ChEBI. This compound is chiefly used in flavor and fragrance sectors, contributing unique sensory characteristics.
Occurrence, Applicability & Potential Uses
Phenyl Pyruvic Acid is found as an intermediate in metabolic pathways involving amino acids such as phenylalanine and is occasionally detected in biological samples. Its aromatic and phenolic sensory attributes make it valuable for flavoring and fragrance applications, including floral and honey notes in products. It is also used to impart character in tobacco and vegetable flavors, as well as green, grassy nuances. The compound's use levels and safety are addressed under standards such as FEMA (US), which catalogs it as FEMA number 3892, recognizing its role as a flavoring agent. Its incorporation into products follows regulatory guidelines ensuring controlled usage levels for consumer safety.
Physico-Chemical Properties Summary
Phenyl Pyruvic Acid exhibits a moderate boiling point in the range of 299 to 300°C at 760 mmHg, reflecting its stability under normal atmospheric pressure. It has a low vapor pressure of 0.001 mmHg at 25°C, indicating low volatility at room temperature. The compound is soluble in water, alcohol, and propylene glycol, facilitating its use in diverse formulations. Its estimated log P value of approximately 0.14 signifies moderate polarity, contributing to balanced solubility and interaction with other formulation components. The flash point is about 100°C (212°F), which is relevant for handling and storage safety assessments. These physico-chemical features support its role in fragrance and flavor compositions, combining adequate stability with effective sensory delivery.
FAQ
What is Phenyl Pyruvic Acid and what are its key characteristics?
Phenyl Pyruvic Acid is an aromatic alpha-keto acid with the molecular formula C9H8O3. It features a phenyl-substituted keto acid structure. The compound is noted for its medium-strength honey-like odor and phenolic, grassy flavor characteristics. It is solid at room temperature and soluble in water, alcohol, and propylene glycol. Key synonyms include 2-oxo-3-phenylpropionic acid and alpha-oxo-benzenepropanoic acid. It is primarily used as a flavor and fragrance agent in the industry.
Where is Phenyl Pyruvic Acid used and how is it applied?
This compound is applied mainly in flavor and fragrance products to impart floral, honey, tobacco, and vegetable notes. It is employed to add complexity to formulations with its sweet, phenolic, and grassy sensory properties. Phenyl Pyruvic Acid's solubility in common solvents allows incorporation into various mediums including beverages, confectionery, and tobacco products. Usage levels are controlled to comply with safety standards, thereby ensuring effective and safe application in consumer goods.
What regulations and safety considerations apply to Phenyl Pyruvic Acid?
Phenyl Pyruvic Acid is recognized under FEMA (US) as FEMA number 3892 and has been assessed by organizations including JECFA and IFRA (Global) for its safety in use within flavor and fragrance products. Recommended maximum usage in fragrance concentrates is typically around 0.5%. Safety data indicate no significant hazard classification under OSHA criteria, and common precautions include avoiding dust inhalation and skin/eye contact. Regulatory references from EFSA (EU) and FDA (US) provide data supporting its controlled use, without health or therapeutic claims.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| 2-oxo-3-phenylpropanoic acid | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 997 |
| Pubchem (sid): | 134974264 |
| Pherobase: | View |
Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| FDA Substances Added to Food (formerly EAFUS): | View |
| CHEBI: | View |
| CHEMBL: | View |
| Golm Metabolome Database: | Search |
| KEGG (GenomeNet): | C00166 |
| HMDB (The Human Metabolome Database): | HMDB00205 |
| FooDB: | FDB008272 |
| YMDB (Yeast Metabolome Database): | YMDB00786 |
| Export Tariff Code: | 2918.30.3000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | phenyl pyruvic acid |
| Trivial Name | Phenylpyruvic acid |
| Short Description | 2-oxo-3-phenylpropionic acid |
| Formula | C9 H8 O3 |
| CAS Number | 156-06-9 |
| FEMA Number | 3892 |
| Flavis Number | 8.109 |
| ECHA Number | 205-847-1 |
| FDA UNII | X7CO62M413 |
| Nikkaji Number | J11.025F |
| Beilstein Number | 2207312 |
| MDL | MFCD00002589 |
| COE Number | 8109 |
| xLogP3-AA | 1.30 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1478 2-oxo-3-phenylpropionic acid |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 156-06-9 ; 2-OXO-3-PHENYLPROPIONIC ACID |
| Synonyms |
|
Suppliers
| Alfa Biotechnology | BOC Sciences |
| Parchem | Penta International |
| Sigma-Aldrich: Aldrich | TCI AMERICA |
| Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 164.16035461426 |
| Boiling Point | 299 to 300°C @ 760 mm Hg |
| Vapor Pressure | 0.001 mmHg @ 25 °C |
| Flash Point TCC Value | 100 °C TCC |
| logP (o/w) | 0.142 est |
| Solubility | |
| alcohol | Yes |
| propylene glycol | Yes |
| water, 6.522e+004 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Honey | |
| sweet, acidic, honey, almond, weedy, phenolic, green | |
| Odor strength | medium , recommend smelling in a 10.00 % solution or less |
| Substantivity | 146 hour(s) at 1.00 % in propylene glycol |
| Luebke, William tgsc, (2006) | At 100.00 %. sweet acidic honey almond weedy phenolic green |
| Flavor Type: Phenolic | |
| sweet, phenolic, grassy, honey, vegetable | |
| Luebke, William tgsc, (2006) | At 80.00 ppm in water. sweet phenolic grassy honey vegetable |
Potential Uses
| Applications | |
| Odor purposes | Floral , Flower shop , Honey , Tobacco |
| Flavoring purposes | Vegetable |
| Other purposes | Grass |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| None - None found. | |
| S 02 - Keep out of the reach of children. S 22 - Do not breath dust. S 24/25 - Avoid contact with skin and eyes. | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavor and fragrance agents | |||
| RIFM Fragrance Material Safety Assessment: Search | |||
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice | |||
| Recommendation for phenyl pyruvic acid usage levels up to: | |||
| 0.5000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | ND (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.09 (μg/capita/day) | ||
| Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS). | |||
| The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library | |||
| publication number: 18 | |||
| Click here to view publication 18 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | - | |
| beverages(nonalcoholic): | 0.50000 | 10.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | 1.00000 | 5.00000 | |
| cheese: | 0.50000 | 5.00000 | |
| chewing gum: | 1.00000 | 5.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | 1.00000 | 5.00000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | 0.50000 | 5.00000 | |
| gelatins / puddings: | 0.50000 | 5.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | 1.00000 | 5.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | 0.50000 | 5.00000 | |
| nut products: | - | - | |
| other grains: | 1.00000 | 5.00000 | |
| poultry: | - | - | |
| processed fruits: | 0.10000 | 1.00000 | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | 50.00000 | 100.00000 | |
| snack foods: | - | - | |
| soft candy: | 1.00000 | 5.00000 | |
| soups: | - | - | |
| sugar substitutes: | 0.50000 | 5.00000 | |
| sweet sauces: | 1.00000 | 5.00000 | |
Safety references
| European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies... |
| European Food Safety Authority (EFSA) reference(s): |
| Flavouring Group Evaluation 55 (FGE.55): Consideration of phenyl-substituted aliphatic alcohols and related aldehydes and esters evaluated by JECFA (63rd meeting) structurally related to phenethyl alcohol, aldehyde, esters and related phenylacetic acid esters evaluated by EFSA in FGE.14 (2005) and aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives evaluated by EFSA in FGE.15 (2005) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):156-06-9 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :997 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 2-oxo-3-phenylpropanoic acid |
| Chemidplus:0000156069 |