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sorbyl isobutyrate
Sorbyl isobutyrate is an ester used as a flavor and fragrance ingredient with green, fruity odor notes including apple and pineapple.
General Material Description
Sorbyl isobutyrate, also known by its IUPAC name Propanoic acid, 2-methyl-, 2,4-hexadien-1-yl ester, is a synthetic ester compound with the molecular formula C10H16O2. This colorless liquid is characterized by its distinctive green and fruity odor, which evokes notes of apple, pineapple, and pear. It is a member of the ester chemical class, widely employed in flavor and fragrance formulations. Synonyms include 2,4-hexadienyl isobutyrate, hexa-2,4-dienyl 2-methylpropanoate, and NSC 195147, among others. The compound is typically produced via chemical synthesis and is registered under PubChem CID 86015, reflecting its recognized chemical identity. Sorbyl isobutyrate's sensory profile and chemical stability make it a valuable ingredient in various flavoring and perfuming applications.
Occurrence, Applicability & Potential Uses
Sorbyl isobutyrate does not occur naturally in significant quantities but is synthesized for use in flavor and fragrance industries. It is valued for imparting green, fruity aromas reminiscent of apple, pear, pineapple, and herbal notes, making it useful in tropical fruit flavor profiles. The compound is approved for use by regulatory bodies such as FEMA (US), where it is designated FEMA number 4134, and its use levels in flavor formulations are defined accordingly. Its application extends to perfuming agents within cosmetics, guided by IFRA (Global) standards that regulate concentration limits to ensure safety in consumer products.
Physico-Chemical Properties Summary
The molecular weight of sorbyl isobutyrate is approximately 168.24 g/mol, and it presents as a colorless liquid under ambient conditions. Its vapor pressure at 25 °C is low (0.104 mmHg), indicating modest volatility. The compound exhibits moderate lipophilicity with an estimated logP of 3.06, which influences its solubility profile and interaction in formulations. Solubility in alcohols is good, while it has limited aqueous solubility, estimated at about 93.91 mg/L at 25 °C. The flash point is measured near 82 °C, pointing to moderate flammability. These properties suggest it is suitable for incorporation into both aqueous and non-aqueous flavor and fragrance matrices, with considerations for handling and storage due to volatility and flammability.
FAQ
What is sorbyl isobutyrate and what are its main characteristics?
Sorbyl isobutyrate is a synthetic ester with the molecular formula C10H16O2. It has a distinctive green, fruity odor that includes apple, pear, and pineapple notes, making it a valued ingredient in flavor and fragrance applications. Also known by several synonyms such as 2,4-hexadienyl isobutyrate, it is a colorless liquid typically used in perfuming agents and flavor formulations.
How and where is sorbyl isobutyrate used in industry?
Sorbyl isobutyrate is primarily used as a flavor and fragrance agent. Its green and fruity aroma profile is employed to enhance tropical fruit flavors and related sensory experiences in food and beverage products. It also finds application as a perfuming agent in cosmetics. Its usage levels are established by regulatory agencies such as FEMA (US) and IFRA (Global) to ensure safe inclusion in consumer products.
What regulations and safety considerations apply to sorbyl isobutyrate?
Sorbyl isobutyrate is recognized by FEMA (US) under number 4134 and has undergone safety assessments by organizations including RIFM and IFRA, which provide guidelines for its maximum concentration in fragrances. It has relatively low toxicity with oral and dermal LD50 values above 5000 mg/kg in animal studies, and no significant hazards have been found according to OSHA and GHS standards. Users are advised to follow standard safety precautions such as avoiding contact with eyes and skin, and to keep it out of reach of children as indicated in safety data sheets.
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 |
| FDA Substances Added to Food (formerly EAFUS): | View |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | HMDB32313 |
| FooDB: | FDB009561 |
| Export Tariff Code: | 2915.60.0000 |
| ChemSpider: | View |
General Material Information
| Preferred name | sorbyl isobutyrate |
| Trivial Name | Propanoic acid, 2-methyl-, 2,4-hexadien-1-yl ester |
| Short Description | 2,4-hexadienyl isobutyrate |
| Formula | C10 H16 O2 |
| CAS Number | 16491-24-0 |
| FEMA Number | 4134 |
| ECHA Number | 240-551-6 |
| FDA UNII | Search |
| Nikkaji Number | J318.214B |
| xLogP3-AA | 2.70 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1782 2,4-hexadienyl isobutyrate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 16491-24-0 ; 2,4-HEXADIENYL ISOBUTYRATE |
| Synonyms |
|
Suppliers
| Axsyn | Bedoukian Research |
| BOC Sciences | Parchem |
| Penta International | Sigma-Aldrich: Aldrich |
| Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 168.2359161377 |
| Vapor Pressure | 0.104 mmHg @ 25 °C |
| Flash Point TCC Value | 82.22 °C TCC |
| logP (o/w) | 3.058 est |
| Solubility | |
| alcohol | Yes |
| water, 93.91 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Green | |
| green, fruity, galbanum, apple, pear, pineapple | |
| Odor strength | medium |
| Substantivity | > 1 hour(s) at 100.00 % |
| General comment | At 100.00 %. green fruity galbanum apple pear pineapple |
Potential Uses
| Applications | |
| Odor purposes | Apple , Galbanum , Green , Herbal , Pear , Pineapple |
| Flavoring purposes | Fruit tropical fruit |
| Cosmetic purposes | Perfuming agents |
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 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: | |
| oral-rat LD50 5000 mg/kg Food and Chemical Toxicology. Vol. 26, Pg. 339, 1988. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Chemical Toxicology. Vol. 26, Pg. 339, 1988. | |
| 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 sorbyl isobutyrate usage levels up to: | |||
| 5.0000 % in the fragrance concentrate. | |||
| 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: 22 | |||
| Click here to view publication 22 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 0.50000 | 10.00000 | |
| beverages(nonalcoholic): | 2.00000 | 20.00000 | |
| beverages(alcoholic): | 2.00000 | 20.00000 | |
| breakfast cereal: | 0.50000 | 10.00000 | |
| cheese: | - | - | |
| chewing gum: | 1.00000 | 20.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | 5.00000 | 25.00000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | 1.00000 | 20.00000 | |
| fruit ices: | 1.00000 | 20.00000 | |
| gelatins / puddings: | 5.00000 | 25.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | 1.00000 | 10.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | 5.00000 | 25.00000 | |
| meat products: | - | - | |
| milk products: | 5.00000 | 25.00000 | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | 5.00000 | 25.00000 | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | 1.00000 | 20.00000 | |
| snack foods: | - | - | |
| soft candy: | 1.00000 | 10.00000 | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | 1.00000 | 25.00000 | |
Safety references
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):16491-24-0 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :86015 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| hexa-2,4-dienyl 2-methylpropanoate |
| Chemidplus:0016491240 |