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(E)-geranyl oxyacetaldehyde
(E)-geranyl oxyacetaldehyde is a fragrance compound characterized by a strong waxy aldehydic rose scent, commonly used as a perfuming agent in the fragrance industry.
General Material Description
(E)-geranyl oxyacetaldehyde, with molecular formula C12H20O2, is a synthetic fragrance compound belonging to the aldehyde chemical family. This colorless to pale-yellow liquid exhibits a pronounced waxy-rose odor with aldehydic and ozone nuances. It is recognized under various chemical synonyms such as 2-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]acetaldehyde and geranyloxyacetaldehyde. The compound is structurally related to the geranyl group connected via an ether linkage to an acetaldehyde moiety, giving it distinctive sensory and chemical properties. Detailed chemical information is available in public repositories including PubChem. (E)-geranyl oxyacetaldehyde is typically synthesized for use in perfumery rather than extracted from natural sources.
Occurrence, Applicability & Potential Uses
(E)-geranyl oxyacetaldehyde occurs predominantly in synthetic form for fragrance applications. It is prized for imparting aldehydic, floral, and chypre-like notes reminiscent of cyclamen, lilac, musk, peony, rose, and tuberose. Ozone and clean accords further enhance its complexity, making it suitable for use in various perfume compositions. Its usage is primarily in the fragrance industry as a perfuming agent rather than as a flavoring substance. Regulatory guidelines such as the International Fragrance Association (IFRA) Code of Practice (Global) provide recommendations on usage levels to ensure consumer safety. It is valued for its substantivity and odor character in fine fragrances and personal care products.
Physico-Chemical Properties Summary
(E)-geranyl oxyacetaldehyde has a molecular weight of approximately 196.29 g/mol and shows moderate volatility with a boiling point near 278 to 279 °C at standard atmospheric pressure. Its refractive index ranges from 1.47 to 1.48 at 20 °C, indicating optical clarity. The specific gravity at 25 °C lies between 0.96 and 0.98, reflecting the density relative to water. With a relatively low vapor pressure of 0.004 mmHg at 25 °C, it maintains good hold in fragrance formulations. The estimated partition coefficient (log P) is around 3.41, indicating moderate lipophilicity which impacts solubility and skin affinity. The flash point of 230 °F (approximately 110 °C) denotes moderate flammability under controlled conditions. This compound is soluble in alcohol but exhibits limited water solubility, influencing its formulation in various media.
FAQ
What is (E)-geranyl oxyacetaldehyde and what are its main applications?
(E)-geranyl oxyacetaldehyde is a synthetic fragrance ingredient characterized by a strong waxy aldehydic rose odor with hints of ozone and floral notes. Its primary application is as a perfuming agent in fragrance compositions, providing aldehydic and floral characteristics to enhance scent complexity. It is not used as a flavoring agent.
How is (E)-geranyl oxyacetaldehyde typically used in fragrance formulations?
In fragrance formulations, (E)-geranyl oxyacetaldehyde is used at concentrations up to 5% in fragrance concentrates, following the International Fragrance Association (IFRA) guidelines. Its moderately low volatility and strong odor make it suitable for imparting long-lasting aldehydic and floral notes in perfumes, personal care products, and other scented items.
What safety and regulatory standards apply to (E)-geranyl oxyacetaldehyde?
(E)-geranyl oxyacetaldehyde is classified under European hazard category Xi as an irritant, specifically irritating to skin and eyes, requiring precautionary handling. Safety data from RIFM and IFRA (Global) provide usage limits and risk management guidelines. It is not approved for flavor use and must be handled with appropriate protective measures to avoid skin and eye contact.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
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| 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 |
| ChemSpider: | View |
General Material Information
| Preferred name | (E)-geranyl oxyacetaldehyde |
| Trivial Name | 2-[[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]oxy]acetaldehyde |
| Short Description | (E)-[(3,7-dimethyl-2,6-octadienyl)oxy]acetaldehyde |
| Formula | C12 H20 O2 |
| CAS Number | 65405-73-4 |
| ECHA Number | 265-743-7 |
| FDA UNII | Search |
| Nikkaji Number | J342.557F |
| xLogP3-AA | 3.00 (est) |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 196.28979492188 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.988 to 8.155 |
| Refractive Index | 1.47 to 1.48 @ 20 °C |
| Boiling Point | 278 to 279°C @ 760 mm Hg |
| Vapor Pressure | 0.004 mmHg @ 25 °C |
| Flash Point TCC Value | 110 °C TCC |
| logP (o/w) | 3.414 est |
| Solubility | |
| alcohol | Yes |
| water, 89.53 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Waxy | |
| clean, waxy, aldehydic, ozone, rose | |
| Odor strength | high , recommend smelling in a 10.00 % solution or less |
| Substantivity | 312 hour(s) at 100.00 % |
| General comment | At 10.00 % in dipropylene glycol. strong clean waxy aldehydic ozone rose |
Potential Uses
| Applications | |
| Odor purposes | Aldehydic , Chypre , Cyclamen , Floral , Lilac , Musk , Peony , Rose , Tuberose |
| Other purposes | Clean , Ozone |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| 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 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36 - Wear suitable protective clothing. | |
| 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. 17, Pg. 789, 1979. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Cosmetics Toxicology. Vol. 17, Pg. 789, 1979. | |
| 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 (E)-geranyl oxyacetaldehyde usage levels up to: | |||
| 5.0000 % in the fragrance concentrate. | |||
| Recommendation for (E)-geranyl oxyacetaldehyde 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):65405-73-4 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :6436989 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| 2-[(2E)-3,7-dimethylocta-2,6-dienoxy]acetaldehyde |
| Chemidplus:0065405734 |