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dihydrojasmone
Dihydrojasmone is a cyclopentenone compound used as a flavor and fragrance agent with medium floral odor and sweet, woody nuances.
General Material Description
Dihydrojasmone, known chemically as 3-methyl-2-(N-pentanyl)-2-cyclopenten-1-one, is a naturally occurring alicyclic ketone characterized by the molecular formula C11H18O. It appears as a colorless liquid and is recognized for its floral and sweet aromatic profile with woody and fresh outdoor nuances. Synonyms include 2-amyl-3-methyl-2-cyclopenten-1-one and various isomeric designations reflecting its cyclopentenone structure attached to a pentyl side chain. For further reference, the compound is indexed under PubChem CID 62378. This compound is typically isolated in trace amounts from natural sources such as osmanthus flower absolute, although it may also be synthesized for use in flavor and fragrance applications.
Occurrence, Applicability & Potential Uses
Dihydrojasmone occurs at trace levels in osmanthus flower absolute and is applicable in both flavor and fragrance industries. The compound contributes floral, fruity, herbal, and woody notes in perfumes and cosmetics, aligning with perfuming agents. Its flavor applications include enhancing tropical fruit, dairy cream, and stone fruit nuances like peach, apricot, and mango. Usage recommendations follow standards such as FEMA (US), under which it has the number 3763. These guidelines inform safe application rates, typically up to 5% in fragrance concentrates. The compound’s sensory versatility supports its inclusion in a range of products from beverages to confectioneries, especially as a modifier to enrich complexity.
Physico-Chemical Properties Summary
Dihydrojasmone possesses moderate volatility and lipophilicity, with an estimated logP of approximately 2.75, indicating balanced solubility favoring organic phases. Its specific gravity ranges between 0.911 and 0.917 at 20 to 25 °C, reflecting a denser liquid state than water. The refractive index varies from 1.676 to 1.682 at 20 °C, consistent with aromatic ketones. Boiling point measurements show 120 to 121 °C at reduced pressure (12 mm Hg), highlighting moderate thermal stability. The compound demonstrates good solubility in alcohol and slight solubility in water, estimated at around 38.82 mg/L at 25 °C, which can influence formulation behavior. Flash point is approximately 110 °C (230 °F), denoting relative safety in manufacturing contexts. Stability testing confirms compatibility with various consumer product matrices, including fine fragrances, detergents, and soaps, without discoloration or degradation under typical usage.
FAQ
What is dihydrojasmone and what are its main uses?
Dihydrojasmone is a synthetic and naturally occurring flavor and fragrance compound characterized by its floral, sweet, and woody aroma profile. Chemically, it is a cyclopentenone derivative with the molecular formula C11H18O. It is primarily used as a perfuming agent in cosmetics and personal care products, and as a flavor ingredient to impart floral and tropical fruit nuances in food and beverage formulations.
Where is dihydrojasmone found naturally, and how is it applied in products?
This compound is found in trace amounts in natural materials such as osmanthus flower absolute. In commercial applications, dihydrojasmone is valued for its complex sensory characteristics that blend floral, fruity, and woody notes. It is used in fragrance compositions to add depth and freshness and in flavorings to enhance tropical fruit and creamy aspects. Its good solubility in alcohol and stability in various formulations support its use across perfumes, detergents, and flavored products.
What are the regulatory guidelines and safety considerations for dihydrojasmone?
Dihydrojasmone is recognized by FEMA (US) under number 3763 and is assessed for safe use as a flavor and fragrance ingredient. IFRA standards recommend maximum usage levels of up to 5% in fragrance concentrates. Safety data indicate low toxicity with oral LD50 in rat studies of 2500 mg/kg and dermal LD50 in rabbits greater than 5000 mg/kg. No significant hazards or precautionary GHS classifications have been identified, and good manufacturing practices including protective measures against skin and eye contact are advised. Regulatory evaluations including those by JECFA and EFSA provide further safety and usage documentation.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| 3-methyl-2-pentylcyclopent-2-en-1-one | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 1128-08-1 |
| Pubchem (cid): | 62378 |
| Pubchem (sid): | 135020452 |
| Pherobase: | View |
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): | HMDB31565 |
| FooDB: | FDB008180 |
| Export Tariff Code: | 2914.29.5000 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | dihydrojasmone |
| Trivial Name | Dihydrojasmone |
| Short Description | 3-methyl-2-(N-pentanyl)-2-cyclopenten-1-one |
| Formula | C11 H18 O |
| CAS Number | 1128-08-1 |
| Deleted CAS Number | 30966-11-1 |
| FEMA Number | 3763 |
| Flavis Number | 7.14 |
| ECHA Number | 214-434-5 |
| FDA UNII | Y953R7PP90 |
| Nikkaji Number | J12.280G |
| Beilstein Number | 1906471 |
| MDL | MFCD00036480 |
| xLogP3-AA | 2.90 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1406 3-methyl-2-(N-pentanyl)-2-cyclopenten-1-one |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 1128-08-1 ; 2-PENTYL-3-METHYL-2-CYCLOPENTEN-1-ONE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 166.26365661621 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.58 to 7.63 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 7.598 to 7.639 |
| Refractive Index | 1.676 to 1.682 @ 20 °C |
| Boiling Point | 120 to 121°C @ 12 mm Hg |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.01 mmHg @ 20 °C |
| Flash Point TCC Value | 110 °C TCC |
| logP (o/w) | 2.754 est |
| Solubility | |
| alcohol | Yes |
| water, very slightly | Yes |
| water, 38.82 mg/L @ 25 °C (est) | Yes |
| water | No |
| Stability | |
| alcoholic fine fragrance | Good |
| antiperspirant | Good |
| fabric softener | Good |
| liquid detergent | Good |
| perborate powder detergent | Good |
| soap | Good |
| toiletry application | Good |
| hair spray | Unspecified |
| lotion | Unspecified |
| non-discoloring in most media | Unspecified |
| powder | Unspecified |
Organoleptic Properties
| Odor Type: Floral | |
| fresh outdoors, jasmin, myrrh, woody, spicy, herbal, fruity, sweet, floral, powdery | |
| Odor strength | medium |
| Substantivity | 340 hour(s) at 100.00 % |
| Luebke, William tgsc, (1984) | At 100.00 %. fresh outdoor jasmin myrrh woody spice herbal |
| Mosciano, Gerard P&F 18, No. 3, 53, (1993) | Fruity, sweet, floral, woody with a powdery nuance |
| Flavor Type: Floral | |
| sweet, floral, green, herbal, citrus | |
| Mosciano, Gerard P&F 18, No. 3, 53, (1993) | At 10.00 ppm. Sweet, floral, green, herbal with a citrus nuance |
| Cream notes for dairy flavors, lactone notes for peach, apricot, mango, and other fruit flavors. | Creamy mouthfeel, lactonic |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Apricot , Bergamot , Celery , Chypre , Citrus , Coconut , Fern , Floral , Fresh outdoors , Green , Herbal , Honey , Jasmin , Lavender , Lily of the valley , Maple , Oriental , Peach , Spice , Woody |
| Flavoring purposes | Fruit tropical fruit , Tropical |
| Other purposes | Modifier , Natural , Seedy , Waxy |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| None - None found. | |
| S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes. 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 2500 mg/kg Food and Cosmetics Toxicology. Vol. 12, Pg. 523, 1974. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Cosmetics Toxicology. Vol. 12, Pg. 523, 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 | |||
| Recommendation for dihydrojasmone usage levels up to: | |||
| 5.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.34 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.20 (μg/capita/day) | ||
| Structure Class: | II | ||
| 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: 15 | |||
| Click here to view publication 15 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | - | |
| beverages(nonalcoholic): | - | 2.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | 85.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 10.00000 | |
| fruit ices: | - | 13.00000 | |
| gelatins / puddings: | - | 10.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 13.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | 13.00000 | |
| meat products: | - | - | |
| milk products: | - | 10.00000 | |
| 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 212: alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.6 of FGE.19 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 212 Revision 1 (FGE.212Rev1): alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.6 of FGE.19. View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 212 Revision 3 (FGE.212Rev3): a,ß-unsaturated alicyclic ketones and precursors from chemical subgroup 2.6 of FGE.19 View page or View pdf |
| Flavouring Group Evaluation 51, Revision 2 (FGE.51Rev2): Consideration of alicyclic ketones and secondary alcohols and related esters evaluated by JECFA (59th meeting) structurally related to alicyclic ketones secondary alcohols and related esters in FGE.09Rev6 (2015) View page or View pdf |
| Safety and efficacy of secondary alicyclic saturated and unsaturated alcohols, ketones, ketals and esters with ketals containing alicyclic alcohols or ketones and esters containing secondary alicyclic alcohols from chemical group 8 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):1128-08-1 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :62378 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| 3-methyl-2-pentylcyclopent-2-en-1-one |
| Chemidplus:0001128081 |
| RTECS:GY7302000 for cas# 1128-08-1 |