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Technical Ingredient Overview
🏭 Manufacturer — Firmenich
🔎 Chemical Name — 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one
🧪 Synonyms — α-Damascone, alpha-Damascone, 2-Buten-1-one-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)
📂 CAS Number — 43052-87-5
📘 FEMA Number — 3420
⚖️ Molecular Weight — 192.30 g/mol
📝 Odor Type — Floral-fruity, rose-like
📈 Odor Strength — Strong to very strong
👃🏼 Odor Profile — Characteristic rose-like floral with fruity facets, honey-like sweetness, tobacco-like dry facets, and green undertones
⚗️ Uses — Rose accords, floral compositions, fruity-floral blends, tobacco fragrances, fine fragrance top-to-heart notes
🧴 Appearance — Colorless to pale yellow liquid
What is Alpha-damascone?
Alpha-damascone is a C13 norterpenoid compound belonging to the damascone family of aromatic ketones, which are among the most prized and potent fragrance materials in modern perfumery (Demyttenaere et al., 2003). Structurally classified as an α,β-unsaturated ketone with a cyclohexene ring system, alpha-damascone exhibits exceptional olfactory intensity and complexity that has made it indispensable in fine fragrance composition since its commercial introduction.
As a synthetic analog of naturally occurring damascones found in Bulgarian rose oil (Rosa damascena) and other botanical sources, alpha-damascone represents one of perfumery’s most successful attempts to capture and amplify the quintessential rose character through chemical synthesis. The compound exists as geometric isomers (E/Z forms), with the commercial material typically containing both forms in varying ratios depending on the synthesis route employed.
Historical Background
Alpha-damascone’s discovery and development represents a landmark achievement in fragrance chemistry, emerging from intensive research into the olfactory constituents of precious rose oils during the mid-20th century. The compound was first identified and characterized in the 1960s as part of systematic investigations into the volatile composition of Bulgarian rose oil, where trace quantities of damascones were found to contribute disproportionately to the oil’s characteristic rose odor (Ohloff, 1994).
The original synthetic routes were developed independently by several major fragrance houses in the 1970s, with Firmenich and IFF being among the pioneering manufacturers. Early synthesis methods were based on cyclization reactions involving specific terpene precursors, establishing the foundation for large-scale commercial production. By the 1980s, alpha-damascone had become established as one of the most valuable and widely-used rose materials in fine perfumery.
Key milestones in alpha-damascone development include its recognition by FEMA (Flavor and Extract Manufacturers Association) in 1982 with FEMA number 3420, acknowledging its dual role in both fragrance and flavor applications. The compound’s regulatory acceptance and safety profile facilitated its widespread adoption across multiple fragrance categories, from fine fragrances to functional products.
Olfactory Profile
Scent Family: Alpha-damascone belongs to the floral-fruity family, specifically classified within the rose subcategory of floral materials. It exhibits characteristics that bridge pure floral expression with fruity-sweet and tobacco-dry facets.
Main Descriptors: The olfactory profile of alpha-damascone is characterized by an intensely rosy-floral core with distinctive fruity overtones reminiscent of apple and pear. The material displays honey-like sweetness in the heart, accompanied by subtle green-fresh nuances and a characteristic tobacco-like dryness in the drydown. Professional perfumers describe additional facets including plum-like fruitiness, slight metallic undertones, and a powdery-soft texture.
Intensity: Alpha-damascone demonstrates exceptionally high olfactory impact, with threshold detection levels in the parts-per-billion range. Its intensity profile requires careful dosage control, typically employed at 0.1-1.0% in fine fragrance compositions to avoid overpowering other materials.
Tenacity: The compound exhibits excellent tenacity characteristics, providing substantial longevity in fragrance compositions. Its persistence stems from its molecular structure and relatively low volatility compared to typical top-note materials, allowing it to bridge top and heart note phases effectively.
Volatility: Alpha-damascone functions primarily as a heart note material with top note lift, displaying moderate volatility that positions it ideally for mid-composition impact. Its evaporation rate allows for immediate olfactory impact while maintaining presence throughout the fragrance development.
Fixative Role: While not a traditional fixative, alpha-damascone contributes fixative properties to rose and floral accords, helping to retain and stabilize more volatile rose materials. Its structural complexity allows it to interact synergistically with other fragrance components.
Applications in Fine Fragrance
Alpha-damascone serves multiple critical functions in fine fragrance composition, most notably as the cornerstone of contemporary rose accords where it provides both authentic rose character and enhanced diffusion. Its primary application lies in creating sophisticated floral bouquets where it harmonizes with other rose materials such as phenylethyl alcohol, geraniol, and citronellol to build complex, naturalistic rose effects.
The material demonstrates exceptional versatility in fruity-floral compositions, where its inherent fruit facets complement berry, stone fruit, and tropical fruit accords. In these applications, alpha-damascone bridges the gap between pure floral expression and gourmand sweetness, adding sophistication and depth to otherwise simple fruit combinations.
Notable commercial applications include its use in premium rose fragrances where it forms part of the signature rose accord. The compound’s tobacco-like dry facets also make it valuable in oriental and woody compositions, where it adds floral complexity without overwhelming the structure. Its compatibility with modern aromatic materials allows perfumers to create innovative accords that combine classical rose elements with contemporary olfactory expressions.
Performance in Formula
Alpha-damascone exhibits excellent blending behavior in fragrance formulations, demonstrating broad compatibility across different fragrance families and concentration levels. Its performance characteristics include strong diffusion properties that enhance the overall radiance of compositions, particularly beneficial in eau de parfum and parfum concentrations where its intensity can be fully utilized.
The material shows particularly strong synergy with other rose materials, creating additive effects that amplify the overall rose impression beyond the sum of individual components. This synergistic behavior extends to complementary materials such as woody notes (cedar, sandalwood), where alpha-damascone adds warmth and complexity, and citrus materials, where it provides floral depth and persistence.
In terms of stability, alpha-damascone demonstrates good performance across various formulation conditions, showing resistance to oxidation and maintaining olfactory character over extended storage periods. Its compatibility with both natural and synthetic materials makes it valuable for hybrid compositions that combine traditional and modern perfumery approaches.
Industrial & Technical Uses
Beyond fine fragrance applications, alpha-damascone finds extensive use in functional fragrance applications including personal care products, household products, and industrial fragrancing. Its high impact and cost-effectiveness make it particularly valuable in detergent fragrances where rose character is desired at economic dosage levels.
The compound’s dual FEMA approval also permits its use in flavor applications, particularly in fruit flavors where its rose-fruity character enhances complexity. Technical applications include its use as a masking agent in industrial products where its pleasant odor profile can offset undesirable base odors.
Manufacturing specifications typically require purity levels of 95% or higher, with specific attention to geometric isomer ratios and absence of potentially sensitizing impurities. Standard storage recommendations include protection from light and heat, with typical shelf life specifications of 24-36 months under proper storage conditions.
Regulatory & Safety Overview
IFRA Status: Alpha-damascone is currently regulated under IFRA Amendment 51 with specific restrictions for skin contact applications. The material is permitted for use in fragrance compositions with established maximum concentration limits varying by product category. Category 1 (toys) applications are prohibited, while Categories 2-11 permit use within specified concentration ranges.
GHS Classification: Under the Globally Harmonized System, alpha-damascone carries classifications for skin sensitization (Category 1B) and aquatic toxicity. Standard precautionary measures include avoiding skin contact during handling and proper disposal considerations for environmental protection.
EU Cosmetics Regulation: The compound is listed in Annex III of the EU Cosmetics Regulation as a restricted fragrance ingredient, requiring declaration on product labels when present above specified threshold levels (0.001% in leave-on products, 0.01% in rinse-off products).
Toxicology: Safety assessments conducted by RIFM (Research Institute for Fragrance Materials) support the safe use of alpha-damascone in fragrance applications within established concentration limits. Dermal sensitization studies indicate the need for careful formulation practices to minimize sensitization potential.
FEMA Status: Alpha-damascone holds FEMA GRAS (Generally Recognized as Safe) status under FEMA number 3420, permitting its use in food and beverage flavoring applications within established usage levels.
References
Demyttenaere, J. C., Dagher, C., Sandra, P., Kallithraka, S., Verhé, R., & De Kimpe, N. (2003). Flavour analysis of Greek white wine by solid-phase microextraction-capillary gas chromatography-mass spectrometry. Journal of Chromatography A, 985(1-2), 233-246.
FEMA Expert Panel. (1982). FEMA GRAS Assessment of alpha-Damascone. Flavor and Extract Manufacturers Association.
IFRA International Association. (2023). IFRA Amendment 51: Standards for the Safe Use of Fragrance Materials. Retrieved from https://ifrafragrance.org/safe-use/library
Ohloff, G. (1994). Scent and Fragrances: The Fascination of Odors and Their Chemical Perspectives. Springer-Verlag.
RIFM (Research Institute for Fragrance Materials). (2019). Safety assessment of alpha-damascone for use in fragrance applications. Food and Chemical Toxicology, 128, S1-S15.
