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geranyl crotonate
Geranyl crotonate is a fragrance ester known for its medium-strength caramellic odor and use as a perfuming agent with characteristic maple and herbal notes.
General Material Description
Geranyl crotonate is an organic ester compound notable for its fragrant properties. Chemically identified as trans-3,7-dimethyl-2,6-octadien-1-ol 2-butenoate, it has the molecular formula C14H22O2, indicating it consists of fourteen carbon atoms, twenty-two hydrogen atoms, and two oxygen atoms. The compound appears as a colorless liquid with a characteristic caramellic odor that combines fruity, sweet, maple, almond, and nutty notes, providing a medium strength scent. It is classified as a fragrance ester and is known under several synonyms including (E)-3,7-dimethyl-2,6-octadienyl 2-butenoate and crotonic acid geraniol ester. This compound is typically obtained through esterification reactions involving geraniol and crotonic acid derivatives. Geranyl crotonate is referenced in databases such as PubChem and is widely used in the flavor and fragrance industries for its distinctive aroma profile.
Occurrence, Applicability & Potential Uses
Geranyl crotonate occurs primarily as a synthetic fragrance ester used in various perfuming applications. It is appreciated for imparting aromatic notes reminiscent of caramel, maple, herbal, and autumnal themes, which makes it useful in complex fragrance blends aiming for warm and sweet profiles. This compound is registered and evaluated under standards such as IFRA (Global), which provide guidance on safe usage levels in fragrance concentrates, recommending concentrations up to 10% in formulations. Although it contributes desirable sensory qualities, geranyl crotonate is not approved for flavor use and therefore is restricted to cosmetic and perfumery applications. Its biological occurrence is limited; geranyl crotonate is mainly produced via synthetic routes for industrial use rather than extracted from natural sources.
Physico-Chemical Properties Summary
Geranyl crotonate is a moderately lipophilic compound, as indicated by its estimated logP value of approximately 4.47, which influences its solubility and volatility. It has a boiling point range closely centered around 302 to 303°C measured at standard atmospheric pressure, reflecting its relative thermal stability and moderate volatility suitable for fragrance evaporation. The vapor pressure at 25°C is very low, about 0.001 mmHg, suggesting slow evaporation under typical ambient conditions. It is soluble in alcohols but exhibits limited solubility in water, with an estimated aqueous solubility around 1.115 mg/L at 25°C. The flash point is relatively high at 292°F (approximately 144°C), indicating safe handling under common storage and use conditions. These physical and chemical characteristics contribute to geranyl crotonate’s persistence and substantivity in fragrance compositions, supporting extended scent longevity.
FAQ
What is geranyl crotonate and what are its key uses?
Geranyl crotonate is an organic ester used primarily as a fragrance ingredient. It is known for its caramellic odor with sweet, maple, fruity, and almond notes. The compound finds applications in perfuming agents, adding warm and herbal aromatic qualities to fragrances. Its use is mainly in cosmetic and personal care products rather than food or flavoring.
How is geranyl crotonate typically sourced and where is it applied?
Geranyl crotonate is usually synthesized through esterification of geraniol and crotonic acid derivatives. It is not commonly found naturally but produced industrially for fragrance formulation. It is applied in perfumes and scented products to impart caramel and autumnal aromas. The compound’s properties, such as moderate boiling point and low vapor pressure, support its functionality in long-lasting fragrance blends.
What regulations and safety considerations apply to geranyl crotonate?
Geranyl crotonate is regulated under the IFRA Code of Practice (Global), which recommends usage levels up to 10% in fragrance concentrates. It is not approved for food flavoring applications. Toxicological data show low acute toxicity via oral or dermal exposure, with no significant hazard classifications under OSHA HCS standards. Safety assessments by organizations such as RIFM confirm its suitability for cosmetic use when following recommended guidelines.
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 |
| HMDB (The Human Metabolome Database): | Search |
| Export Tariff Code: | 2916.19.7000 |
| ChemSpider: | View |
General Material Information
| Preferred name | geranyl crotonate |
| Trivial Name | Geranyl crotonate |
| Short Description | trans-3,7-dimethyl-2,6-octadien-1-ol 2-butenoate |
| Formula | C14 H22 O2 |
| CAS Number | 56172-46-4 |
| ECHA Number | 260-027-0 |
| FDA UNII | Search |
| Nikkaji Number | J65.642I |
| xLogP3-AA | 4.30 (est) |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
| Grau Aromatics | Penta International |
| SRS Aromatics | Synerzine |
| Penta International Corporation | SRS Aromatics Ltd |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 222.32774353027 |
| Boiling Point | 302 to 303°C @ 760 mm Hg |
| Vapor Pressure | 0.001 mmHg @ 25 °C |
| Flash Point TCC Value | 144.44 °C TCC |
| logP (o/w) | 4.471 est |
| Solubility | |
| alcohol | Yes |
| water, 1.115 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Caramellic | |
| sweet, caramellic, maple, fruity, almond, acorn, nutty | |
| Odor strength | medium |
| Substantivity | 51 hour(s) at 100.00 % |
| Luebke, William tgsc, (1984) | At 100.00 %. sweet caramel maple fruity almond acorns nutty |
Potential Uses
| Applications | |
| Odor purposes | Acorn , Autumn , Herbal , Maple |
| Flavoring purposes | Caramel |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| 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 Cosmetics Toxicology. Vol. 12, Pg. 891, 1974. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Cosmetics Toxicology. Vol. 12, Pg. 891, 1974. | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| 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 geranyl crotonate usage levels up to: | |||
| 10.0000 % in the fragrance concentrate. | |||
| Recommendation for geranyl crotonate flavor usage levels up to: | |||
| not for flavor use. | |||
Safety references
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):56172-46-4 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5980396 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| [(2E)-3,7-dimethylocta-2,6-dienyl] (E)-but-2-enoate |
| Chemidplus:0056172464 |