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cinnamyl isovalerate
Cinnamyl isovalerate is an ester compound used primarily as a flavor and fragrance agent with fruity and spicy characteristics.
General Material Description
Cinnamyl isovalerate is an ester compound with the molecular formula C14H18O2, known for its characteristic fruity and spicy odor and flavor properties. It is also referenced by several synonyms, including cinnamyl 3-methyl butanoate and 3-phenyl-2-propenyl 3-methyl butanoate. This compound appears as a clear liquid with a refractive index between 1.518 and 1.524 at 20 °C. It is naturally present in certain concrete extracts such as champaca concrete and is valued in flavor and fragrance applications for its apple-like, fruity nuance combined with spicy complexity. The PubChem database lists cinnamyl isovalerate under CID 61091 as a flavoring ester derived from cinnamyl alcohol and isovaleric acid.
Occurrence, Applicability & Potential Uses
Cinnamyl isovalerate naturally occurs in small quantities in plant extracts like champaca concrete. It is widely used as both a flavor and fragrance agent due to its distinctive medium-strength spicy odor combined with fruity notes reminiscent of apple, cherry, blueberry, and melon. Regulatory standards such as IFRA (Global) provide guidelines for maximum skin concentration, and FEMA (US) assigns it the number 2302, reflecting its acceptance as a flavoring substance. The ester finds applicability in flavor formulations for bakery products, spicy condiments, and nut-related flavors, as well as in perfuming agents within cosmetic products. Its use in fragrance concentrates is typically limited to low percentages to maintain safety and efficacy.
Physico-Chemical Properties Summary
Cinnamyl isovalerate is a moderately dense liquid with a specific gravity range of 0.992 to 0.996 at 25 °C, and a refractive index close to 1.52 at 20 °C. It boils between 313 and 315 °C at atmospheric pressure (760 mm Hg), exhibiting a relatively low vapor pressure of 0.00026 mmHg at 25 °C. Its flash point is approximately 212 °F (100 °C), indicating moderate flammability under certain conditions. The compound has a logP value estimated at 4.013, revealing lipophilic character that affects its solubility profile. It is soluble in alcohols and fixed oils but practically insoluble in water, propylene glycol, and glycerin, which impacts its formulation use in aqueous and semi-polar systems.
FAQ
What is cinnamyl isovalerate and what are its primary characteristics?
Cinnamyl isovalerate is an ester formed from cinnamyl alcohol and isovaleric acid, used predominantly as a flavor and fragrance ingredient. It exhibits a medium-strength spicy odor accompanied by fruity nuances such as apple, cherry, blueberry, and melon. The compound appears as a transparent liquid with chemical formula C14H18O2 and has synonyms including cinnamyl 3-methyl butanoate and 3-phenylprop-2-enyl 3-methylbutanoate.
Where does cinnamyl isovalerate naturally occur and how is it typically used?
This ester is naturally found at low levels in certain plant extracts, specifically champaca concrete at about 0.01%. Industrially, it is used as a flavoring agent to impart fruity and spicy notes to products such as baked goods and savory spices. It also serves as a perfuming agent in cosmetics. Regulatory frameworks like IFRA (Global) set safe usage levels to avoid skin irritation.
What safety and regulatory information is relevant to cinnamyl isovalerate?
Cinnamyl isovalerate is classified as an irritant under European guidelines, requiring protective measures to prevent skin and eye irritation. Its FEMA number is 2302, and it is recognized as generally safe for use in food flavorings within prescribed limits. IFRA guidelines recommend maximum use levels in fragrances, often below 0.03% in finished cosmetics. Toxicological studies indicate low acute toxicity with high LD50 values in animal models.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| Perfumer & Flavorists | Start search |
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| 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 |
| HMDB (The Human Metabolome Database): | HMDB41318 |
| FooDB: | FDB021237 |
| Export Tariff Code: | 2916.19.5000 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | cinnamyl isovalerate |
| Trivial Name | Cinnamyl isovalerate |
| Short Description | 3-phenyl-2-propenyl 3-methyl butanoate |
| Formula | C14 H18 O2 |
| CAS Number | 140-27-2 |
| FEMA Number | 2302 |
| Flavis Number | 9.459 |
| ECHA Number | 205-407-9 |
| FDA UNII | 5JHK9Y2XRM |
| MDL | MFCD00048351 |
| COE Number | 454 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 654 cinnamyl isovalerate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 140-27-2 ; CINNAMYL ISOVALERATE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | Yes |
| Molecular weight | 218.29585266113 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.254 to 8.288 |
| Refractive Index | 1.518 to 1.524 @ 20 °C |
| Boiling Point | 313 to 315°C @ 760 mm Hg |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.00026 mmHg @ 25 °C |
| Vapor Density | 7.5 |
| Flash Point TCC Value | 100 °C TCC |
| logP (o/w) | 4.013 est |
| Solubility | |
| alcohol | Yes |
| fixed oils | Yes |
| water, 8.282 mg/L @ 25 °C (est) | Yes |
| water | No |
| propylene glycol | No |
| glycerin | No |
Organoleptic Properties
| Odor Type: Spicy | |
| sweet, spicy, melon, cherry, apple green apple, sour, fermented, winey, yeasty, woody, fruity | |
| Odor strength | medium |
| Substantivity | 100 hour(s) at 100.00 % |
| Luebke, William tgsc, (1985) | At 100.00 %. sweet spice melon cherry green apple |
| Mosciano, Gerard P&F 25, No. 4, 71, (2000) | At 1.00 %. Sour, fermented and winey, yeasty with woody and fruity nuances |
| Flavor Type: Fruity | |
| fruity, winey, fermented, pear, honey, blueberry | |
| Mosciano, Gerard P&F 25, No. 4, 71, (2000) | At 1.00 - 10.00 ppm. Fruity, winey, fermented with pear, honey blueberry nuances |
| General comment | APPLE-LIKE |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Apple , Apricot , Blueberry , Cherry , Grape , Maple , Melon , Peach , Pear , Pineapple , Plum , Rose , Rose tea rose , Spice , Strawberry |
| Flavoring purposes | Bread , Pepper tabasco pepper , Walnut |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/38 - Irritating to skin and eyes. S 02 - Keep out of the reach of children. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 37/39 - Wear suitable gloves and eye/face protection. | |
| 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. | |
| Human Experience: | |
| 2 % solution: no irritation or sensitization. | |
| Oral/Parenteral Toxicity: | |
| oral-rat LD50 5000 mg/kg Food and Cosmetics Toxicology. Vol. 12, Pg. 857, 1974. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Cosmetics Toxicology. Vol. 12, Pg. 857, 1974. | |
| 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 | |||
| maximum skin levels for fine fragrances: | |||
| 0.0020 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey).(IFRA, 2001) | |||
| Recommendation for cinnamyl isovalerate usage levels up to: | |||
| 4.0000 % in the fragrance concentrate. | |||
| use level in formulae for use in cosmetics: | |||
| 0.0300 % | |||
| Dermal Systemic Exposure in Cosmetic Products: | |||
| 0.0008 mg/kg/day (IFRA, 2001) | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 3.90 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 8.00 (μg/capita/day) | ||
| Structure Class: | I | ||
| 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: 3 | |||
| Click here to view publication 3 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 3.60000 | |
| beverages(nonalcoholic): | - | 2.20000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | 19.00000 | 30.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 2.60000 | |
| fruit ices: | - | 2.60000 | |
| gelatins / puddings: | - | 11.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 4.10000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
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 214: alpha,beta-Unsaturated aldehydes and precursors from chemical subgroup 3.1 of FGE.19: Cinnamyl derivatives[1] View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 68 (FGE.68): Consideration of cinnamyl alcohol and related flavouring agents evaluated by JECFA (55th meeting) evaluated by EFSA in FGE.15Rev1 (2008) View page or View pdf |
| Safety and efficacy of aryl-substituted primary alcohol, aldehyde, acid, ester and acetal derivatives belonging to chemical group 22 when used as flavourings for all animal species View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):140-27-2 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :61091 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| 3-phenylprop-2-enyl 3-methylbutanoate |
| Chemidplus:0000140272 |
| RTECS:EK7902515 for cas# 140-27-2 |