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sodium 4-methyl-2-oxovalerate
Sodium 4-methyl-2-oxovalerate is a sodium salt compound used primarily as a buttery flavoring agent in food products.
General Material Description
Sodium 4-methyl-2-oxovalerate, also known as sodium alpha-ketoisocaproate, is the sodium salt form of 4-methyl-2-oxopentanoic acid. This compound has the molecular formula C6H9O3Na and appears as a solid that is soluble in water. It is valued primarily for its buttery odor and flavor characteristics, contributing to the sensory profile of various food products. Synonyms include 4-methyl-2-oxopentanoic acid sodium salt and 2-ketoisocaproic acid sodium salt among others. It is listed in chemical repositories such as PubChem, providing detailed chemical information and structure data. The compound is typically derived and used in flavoring applications where it imparts buttery notes.
Occurrence, Applicability & Potential Uses
Biologically, sodium 4-methyl-2-oxovalerate is related to alpha-keto acids involved in amino acid metabolism, particularly leucine catabolism. Industrially, it is applied predominantly as a flavoring agent to introduce buttery notes in food products, including dairy and processed food categories. This compound is recognized and reviewed by standards bodies including FEMA (US), which assigns it the number 3871 and evaluates its safety and usage levels. Its application spans beverages, dairy, confectionery, seasonings, and other flavored food items, reflecting its broad functionality in formulation.
Physico-Chemical Properties Summary
Sodium 4-methyl-2-oxovalerate exhibits a molecular weight of approximately 152.13 g/mol and contains the sodium salt of a keto acid. It has a water solubility estimated at 167,600 mg/L at 25 °C, indicating high hydrophilicity. The compound has a low estimated logP value of 0.17, suggesting limited lipophilicity, which influences its behavior in aqueous and lipid media. It has a boiling point range of 190 to 191 °C at 760 mmHg and a modest vapor pressure of 0.239 mmHg at 25 °C, indicating low volatility. The flash point is around 182 °F (approximately 83 °C). For storage, it requires a cool, dry place away from heat and light, with a shelf life typically extending 24 months or more if properly maintained. These properties ensure its stability and suitability for use in flavoring systems.
FAQ
What is sodium 4-methyl-2-oxovalerate and its primary use?
Sodium 4-methyl-2-oxovalerate is the sodium salt of 4-methyl-2-oxopentanoic acid, a keto acid derivative. It is primarily used as a flavoring agent to impart a buttery aroma and taste in various food products. It belongs to the class of compounds known for contributing to buttery sensory characteristics. Its use is well established in flavor formulation due to its characteristic odor properties.
How is sodium 4-methyl-2-oxovalerate applied in food products and where does it occur naturally?
This compound is applied in a range of food products, including dairy, beverages, seasonings, and confectionery, to add buttery flavor notes. It occurs biologically as a metabolite related to amino acid catabolism, especially in leucine degradation pathways. The compound’s chemical properties make it compatible for use in aqueous-based formulations, contributing to the desired sensory quality without significant volatility or degradation.
What regulatory standards govern the use of sodium 4-methyl-2-oxovalerate and how is it sourced?
Sodium 4-methyl-2-oxovalerate is evaluated by FEMA (US) under number 3871, which assesses its safety and recommended usage levels in food flavorings. The compound is approved for use in various food categories with established maximum concentration limits. It is commercially produced as a synthetically derived sodium salt and is available from chemical suppliers with appropriate purity for flavor applications. Safety data indicate no classified hazards under OSHA HCS 29 CFR 1910.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
| Google Books | Start search |
| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
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 |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | Search |
| Export Tariff Code: | 2918.30.5000 |
| ChemSpider: | View |
| FAO: | 4-Methyl-2-oxopentanoic acid, sodium salt |
General Material Information
| Preferred name | sodium 4-methyl-2-oxovalerate |
| Trivial Name | Sodium α-ketoisocaproate |
| Short Description | 4-methyl-2-oxopentanoic acid, sodium salt |
| Formula | C6 H9 O3 Na |
| CAS Number | 4502-00-5 |
| FEMA Number | 3871 |
| ECHA Number | 224-816-3 |
| FDA UNII | 815X976CPY |
| Nikkaji Number | J205.882K |
| Beilstein Number | 4239297 |
| MDL | MFCD00064193 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 633.1 4-methyl-2-oxopentanoic acid, sodium salt |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 152.12510681152 |
| Boiling Point | 190 to 191°C @ 760 mm Hg |
| Vapor Pressure | 0.239 mmHg @ 25 °C |
| Flash Point TCC Value | 83.33 °C TCC |
| logP (o/w) | 0.17 est |
| Shelf life | 24 months (or longer if stored properly.) |
| Storage notes | Store in cool, dry place in tightly sealed containers, protected from heat and light. |
| Solubility | |
| water, 1.676e+005 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Buttery | |
| buttery | |
| Luebke, William tgsc, (2007) | At 100.00 %. butyric valeric buttery |
Potential Uses
| Applications | |
| Flavoring purposes | Butter |
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: | |||
| flavoring agents | |||
| Recommendation for sodium 4-methyl-2-oxovalerate usage levels up to: | |||
| not for fragrance use. | |||
| 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): | 0.05000 | 5.00000 | |
| beverages(alcoholic): | 1.00000 | 5.00000 | |
| breakfast cereal: | - | - | |
| cheese: | 1.00000 | 10.00000 | |
| chewing gum: | 0.50000 | 5.00000 | |
| condiments / relishes: | 1.00000 | 5.00000 | |
| confectionery froastings: | 1.00000 | 5.00000 | |
| egg products: | - | - | |
| fats / oils: | 0.50000 | 5.00000 | |
| fish products: | - | - | |
| frozen dairy: | 0.50000 | 10.00000 | |
| fruit ices: | 1.00000 | 5.00000 | |
| gelatins / puddings: | 0.50000 | 5.00000 | |
| granulated sugar: | - | - | |
| gravies: | 1.00000 | 5.00000 | |
| hard candy: | 0.10000 | 5.00000 | |
| imitation dairy: | 0.50000 | 5.00000 | |
| instant coffee / tea: | 0.10000 | 1.00000 | |
| jams / jellies: | 1.00000 | 5.00000 | |
| meat products: | - | - | |
| milk products: | 1.00000 | 10.00000 | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | 0.10000 | 1.00000 | |
| processed vegetables: | 0.10000 | 1.00000 | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | 50.00000 | 100.00000 | |
| snack foods: | - | - | |
| soft candy: | 0.30000 | 3.00000 | |
| soups: | 1.00000 | 10.00000 | |
| sugar substitutes: | 0.50000 | 5.00000 | |
| sweet sauces: | 1.00000 | 10.00000 | |
Safety references
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :4137900 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| sodium 4-methyl-2-oxopentanoate |
| Chemidplus:0004502005 |