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beta-damascone
Beta-damascone is a naturally occurring fragrance compound with a fruity, floral aroma used in flavors and perfumes, sourced from plants including rose and grapefruit juice.
General Material Description
Beta-damascone is a fragrant organic compound classified chemically as a ketone, with the molecular formula C13H20O. It is known by several synonymous names including 1-(2,6,6-trimethyl-1-cyclohexenyl)-2-buten-1-one and rose ketone beta. This compound exhibits a strong fruity and floral scent profile, often described as reminiscent of black currant, plum, rose, and honey aromas. Its sensory properties make it valuable in both flavor and fragrance applications. Beta-damascone occurs naturally in various plants such as roses, grapefruit juice, tea leaves, and tobacco. It is sourced primarily through extraction from these natural materials or synthesized for industrial use. For detailed chemical information, see the PubChem entry.
Occurrence, Applicability & Potential Uses
Beta-damascone is naturally found in diverse botanicals including grapefruit juice, rose petals, tea leaves, and tobacco. It is also present in minute quantities in vassoura oil from Baccharis dracunculifolia. Its compelling fruity and floral aroma makes it useful as a key ingredient in flavor and fragrance formulations. Beta-damascone is employed in a wide variety of products, enhancing fruity notes such as apple, berry, plum, and tropical fruit, as well as floral and tobacco nuances. It is incorporated under standards such as FEMA (US) for flavoring substances and IFRA (Global) for fragrance safety, guiding its safe use levels in consumer goods.
Physico-Chemical Properties Summary
Beta-damascone has a molecular weight of approximately 192.3 g/mol and a chemical formula of C13H20O. It presents as a moderately dense liquid with a specific gravity near 0.925 to 0.932 at 25 °C and a refractive index ranging from 1.496 to 1.5 at 20 °C. Its vapor pressure is low, about 0.007 mmHg at 25 °C, indicating modest volatility. The estimated logP value of 3.3 suggests moderate lipophilicity. It is soluble in alcohol and slightly soluble in water at approximately 7.99 mg/L (estimation at 25 °C). The compound’s flash point is around 200 °F (93 °C), defining safe handling temperatures. Shelf life exceeds 12 months if stored properly in a cool, dry, and well-sealed environment protected from heat and light. These physical and chemical characteristics influence its stability and release profile in consumer formulations.
FAQ
What is beta-damascone and what are its main characteristics?
Beta-damascone is a naturally occurring ketone known for its distinctive fruity and floral aroma. Chemically designated as 1-(2,6,6-trimethyl-1-cyclohexenyl)-2-buten-1-one, it belongs to a group of fragrance compounds commonly used in flavor and fragrance industries. It exhibits scent notes including black currant, plum, rose, and honey. The compound can be found in natural sources such as grapefruit juice, rose, tea leaves, and tobacco, contributing to their characteristic aromas.
Where is beta-damascone typically found and how is it used in industry?
Beta-damascone occurs naturally in various plants including roses, grapefruit juice, tea leaves, and tobacco. In the industry, it is used to impart fruity, floral, and spicy notes to flavors and fragrances. It enhances a wide range of products, providing complexity to items such as perfumes, personal care formulations, food flavors, and tobacco blends. Usage adheres to safety standards, ensuring the compound contributes effectively to product scent and taste profiles.
What regulatory guidelines and safety considerations apply to beta-damascone?
Beta-damascone is regulated under several frameworks including FEMA (US) for flavoring substances and IFRA (Global) standards for fragrance ingredients. IFRA guidelines restrict its concentration in finished products due to its potential for dermal sensitization, recommending maximum usage levels depending on product category. Safety assessments categorize it as a skin irritant requiring protective handling measures. Users should follow storage recommendations to preserve stability and consult relevant regulatory documents for compliance in specific applications.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| Google Books | Start search |
| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| 1-(2,6,6-trimethyl-1-cyclohexenyl)but-2-en-1-one | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 32052 |
| Pubchem (sid): | 135018635 |
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): | HMDB32541 |
| FooDB: | FDB010416 |
| Export Tariff Code: | 2914.29.0000 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | beta-damascone |
| Trivial Name | 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one |
| Short Description | 1-(2,6,6-trimethyl-1-cyclohexenyl)-2-buten-1-one |
| Formula | C13 H20 O |
| CAS Number | 35044-68-9 |
| FEMA Number | 3243 |
| FDA UNII | J131X1Y3RE |
| xLogP3-AA | 3.50 (est) |
| NMR Predictor | External link |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 35044-68-9 ; 4-(2,6,6-TRIMETHYLCYCLOHEX-1-ENYL)BUT-2-EN-4-ONE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 192.30160522461 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.697 to 7.755 |
| Refractive Index | 1.496 to 1.5 @ 20 °C |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.007 mmHg @ 25 °C |
| Flash Point TCC Value | 93.33 °C TCC |
| logP (o/w) | 3.312 est |
| Shelf life | 12 months (or longer if stored properly.) |
| Storage notes | Store in cool, dry place in tightly sealed containers, protected from heat and light. |
| Solubility | |
| alcohol | Yes |
| water, 7.986 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Fruity | |
| fruity, floral, currant black currant, plum, rose, honey, tobacco | |
| Odor strength | high , recommend smelling in a 1.00 % solution or less |
| Substantivity | 191 hour(s) at 100.00 % |
| Luebke, William tgsc, (1987) | At 1.00 % in dipropylene glycol. fruity floral black currant plum rose honey tobacco |
| Flavor Type: Fruity | |
| fruity, green, jammy, berry, tropical, tobacco, plum, honey | |
| Luebke, William tgsc, (1987) | Fruity green jammy berry tropical tobacco plum honey |
Occurrences
| (data available) |
Potential Uses
Safety Information
Safety information
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 43 - May cause sensitisation by skin contact. S 02 - Keep out of the reach of children. S 24 - Avoid contact with skin. S 36 - Wear suitable protective clothing. | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| Acute toxicity, Oral (Category 5), H303 Skin sensitisation (Category 1), H317 | |
| GHS Label elements, including precautionary statements | |
| Pictogram |  |
| Signal word | Warning |
| Hazard statement(s) | |
| H303 - May be harmfulif swallowed H317 - May cause an allergic skin reaction | |
| Precautionary statement(s) | |
| P261 - Avoid breathing dust/fume/gas/mist/vapours/spray. P272 - Contaminated work clothing should not be allowed out of the workplace. P280 - Wear protective gloves/protective clothing/eye protection/face protection. P302 + P352 - IF ON SKIN: wash with plenty of soap and water. P333 + P313 - IF SKIN irritation or rash occurs: Get medical advice/attention. P363 - Wash contaminated clothing before reuse. P501 - Dispose of contents/ container to an approved waste disposal plant. | |
| Oral/Parenteral Toxicity: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| 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 | |||
| IFRA Critical Effect: | |||
| Dermal sensitization | |||
| IFRA fragrance material specification: | |||
| Should not be used as fragrance ingredients such that the total level in finished cosmetic products exceeds 0.02%, individually or in combination. Based on test data showing sensitising potential for these materials and on evidence of cross-reactivity. (IFRA guidelines) | |||
| View the IFRA Standard | |||
| View IFRA Standards Library for complete information. | |||
| Please review Amendment 49 IFRA documentation for complete information. | |||
| IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%): | |||
| Category 1: Products applied to the lips | |||
| 0.0077 % | |||
| Category 2: Products applied to the axillae | |||
| 0.0023 % | |||
| Category 3: Products applied to the face/body using fingertips | |||
| 0.046 % | |||
| Category 4: Products related to fine fragrance | |||
| 0.043 % | |||
| Category 5: Products applied to the face and body using the hands (palms), primarily leave-on | |||
| Category 5A: Body lotion products applied to the body using the hands (palms), primarily leave-on | |||
| 0.011 % | |||
| Category 5B: Face moisturizer products applied to the face using the hands (palms), primarily leave-on | |||
| 0.011 % | |||
| Category 5C: Hand cream products applied to the hands using the hands (palms), primarily leave-on | |||
| 0.011 % | |||
| Category 5D: Baby Creams, baby Oils and baby talc | |||
| 0.011 % | |||
| Category 6: Products with oral and lip exposure | |||
| 0.025 % | |||
| Category 7: Products applied to the hair with some hand contact | |||
| Category 7A: Rinse-off products applied to the hair with some hand contact | |||
| 0.088 % | |||
| Category 7B: Leave-on products applied to the hair with some hand contact | |||
| 0.088 % | |||
| Category 8: Products with significant anogenital exposure | |||
| 0.0045 % | |||
| Category 9: Products with body and hand exposure, primarily rinse off | |||
| 0.084 % | |||
| Category 10: Household care products with mostly hand contact | |||
| Category 10A: Household care excluding aerosol products (excluding aerosol/spray products) | |||
| 0.30 % | |||
| Category 10B: Household aerosol/spray products | |||
| 0.30 % | |||
| Category 11: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate | |||
| Category 11A: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure | |||
| 0.17 % | |||
| Category 11B: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure | |||
| 0.17 % | |||
| Category 12: Products not intended for direct skin contact, minimal or insignificant transfer to skin | |||
| No Restriction | |||
| Notes: | |||
| IFRA FLAVOR REQUIREMENTS: | |||
Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards. | |||
| 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: 4 | |||
| Click here to view publication 4 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 10.00000 | |
| beverages(nonalcoholic): | - | 10.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | 10.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 10.00000 | |
| fruit ices: | - | 10.00000 | |
| gelatins / puddings: | - | 10.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 10.00000 | |
| 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 Authority (EFSA) reference(s): |
| Flavouring Group Evaluation 213: alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.7 of FGE.19 View page or View pdf |
| List of apha, beta-Unsaturated Aldehydes and Ketones representative of FGE.19 substances for Genotoxicity Testing [1] - Statement of the Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF) View page or View pdf |
| Safety of 31 flavouring compounds belonging to different chemical groups when used as feed additives 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):35044-68-9 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :32052 |
| National Institute of Allergy and Infectious Diseases:Data |
| SCCNFP:opinion |
| WGK Germany:2 |
| 1-(2,6,6-trimethyl-1-cyclohexenyl)but-2-en-1-one |
| Chemidplus:0035044689 |