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(E)-beta-ionone
(E)-beta-ionone is a naturally occurring flavor and fragrance molecule characterized by floral and woody notes, commonly used in perfumes and flavorings.
General Material Description
(E)-beta-ionone is a naturally derived organic compound belonging to the ionone class, known for its significant role as a flavor and fragrance ingredient. It typically appears as a colorless to pale yellow liquid with a molecular formula of C13H20O. Sensory evaluation describes it as having medium strength floral, woody, and powdery aromatic notes, often associated with orris, violet, and berry nuances. Listing numerous synonyms, including trans-beta-ionone, the compound is found in various essential oils and fruits. It is sourced by extraction from natural materials such as certain flower and fruit oils or via synthetic routes that preserve its stereochemistry. The PubChem database provides an authoritative link for detailed chemical information on (E)-beta-ionone.
Occurrence, Applicability & Potential Uses
(E)-beta-ionone is widely present in nature, occurring in several fruits including grapes, peaches, papayas, and raspberries as well as in plant oils like cistus and champaca. Its presence contributes to characteristic floral and fruity aromas in these natural sources. The compound finds application chiefly as a flavor and fragrance agent, leveraged for its woody, floral, and fruity sensory properties. It is employed to impart notes such as violet, cherry, and pineapple in various consumer products. Regulatory frameworks including FEMA (US) permit its use within defined limits in foods and fragrances, ensuring safe application and consumer protection.
Physico-Chemical Properties Summary
(E)-beta-ionone exhibits physicochemical characteristics influential to formulation and stability. It has a boiling point between 266 and 269°C at standard atmospheric pressure, reflecting moderate volatility. Its logP is estimated at 3.71, indicating significant lipophilicity, which affects solubility and partitioning behavior. The compound dissolves in alcohol and is sparingly soluble in water (approximately 25.16 mg/L at 25°C), which should be considered when designing aqueous formulations. The flash point is about 112°C (233°F), an important safety parameter in handling and storage. Low vapor pressure at ambient temperature reflects limited evaporation tendency, facilitating longevity in fragranced products.
FAQ
What is (E)-beta-ionone and what are its sensory characteristics?
(E)-beta-ionone is an organic compound known for its flavor and fragrance properties. It is recognized for its medium strength floral and woody aroma, often described as powdery or berry-like. This compound contributes violet, cherry, and orris-like notes in perfumes and flavor formulations. It naturally occurs in various fruits and essential oils.
In which natural sources is (E)-beta-ionone found and how is it used industrially?
(E)-beta-ionone occurs naturally in fruits such as grapes, peaches, raspberries, and papayas and in essential oils like cistus and champaca. Industrially, it is used as a flavor and fragrance agent in products ranging from fine perfumes to food flavorings, imparting floral, fruity, and woody notes that enhance sensory experiences.
What are the regulatory considerations and safety information for (E)-beta-ionone?
(E)-beta-ionone is regulated under FEMA (US) guidelines permitting its controlled use in flavors and fragrances. It is classified as an irritant with potential sensitization effects upon skin contact; therefore, safe use levels are specified in cosmetic and fragrance formulations. Safety data recommend avoiding environmental release, and proper protective measures should be applied during handling. It is generally recognized as safe within recommended concentration limits.
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 |
Literature & References
| (E)-4-[(5R)-5,6,6-trimethylcyclohexen-1-yl]but-3-en-2-one | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 79-77-6 |
| Pubchem (cid): | 6433147 |
| Pubchem (sid): | 134971684 |
| Flavornet: | 79-77-6 |
| 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 |
| KEGG (GenomeNet): | C12287 |
| HMDB (The Human Metabolome Database): | HMDB36565 |
| YMDB (Yeast Metabolome Database): | YMDB01643 |
| Export Tariff Code: | 2914.23.0000 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | (E)-beta-ionone |
| Trivial Name | β-Ionone |
| Short Description | (E)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one |
| Formula | C13 H20 O |
| CAS Number | 79-77-6 |
| Deleted CAS Number | 1353674-22-2 |
| FEMA Number | 2595 |
| ECHA Number | 201-224-3 |
| FDA UNII | A7NRR1HLH6 |
| Beilstein Number | 1909544 |
| MDL | MFCD00001549 |
| COE Number | 142 |
| xLogP3-AA | 3.30 (est) |
| NMR Predictor | External link |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | Yes |
| Molecular weight | 192.30160522461 |
| Boiling Point | 266 to 269°C @ 760 mm Hg |
| Vapor Pressure | 0.004 mmHg @ 25 °C |
| Flash Point TCC Value | 111.67 °C TCC |
| logP (o/w) | 3.71 est |
| Solubility | |
| alcohol | Yes |
| water, 25.16 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Floral | |
| dry, powdery, floral, woody, orris, berry, seedy, sweet, fruity | |
| Odor strength | medium |
| Substantivity | > 48 hour(s) at 100.00 % |
| Luebke, William tgsc, (1998) | At 10.00 % in dipropylene glycol. dry powdery floral woody orris berry seedy |
| Mosciano, Gerard P&F 16, No. 4, 45, (1991) | Sweet, fruity, woody, berry-like with floral and seedy nuances |
| Flavor Type: Woody | |
| woody, floral, waxy, berry, fruity, powdery | |
| Luebke, William tgsc, (1998) | Woody floral waxy berry fruity powdery |
| Mosciano, Gerard P&F 16, No. 4, 45, (1991) | At 20.00 ppm. Woody, floral, berry, fruity with powdery nuances |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Amber , Cherry , Floral , Grape , Lily of the valley , Orris , Pineapple , Plum , Powder , Raspberry , Violet , Woody |
| Cosmetic purposes | Astringents , Perfuming agents |
Safety Information
Safety information
| European information : | |
| Most important hazard(s): | |
| Xi N - Irritant, Dangerous for the environment. | |
| R 36 - Irritating to eyes. R 43 - May cause sensitisation by skin contact. R 51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 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 36/37 - Wear suitable protective clothing and gloves. S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet. | |
| 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: | |
| 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: | |||
| Sensitization | |||
| IFRA Other Specification: | |||
| maximum skin levels for fine fragrances: | |||
| 1.4600 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey).(IFRA, 2001) | |||
| Recommendation for (E)-beta-ionone usage levels up to: | |||
| 10.0000 % in the fragrance concentrate. | |||
| use level in formulae for use in cosmetics: | |||
| 3.1100 % | |||
| Dermal Systemic Exposure in Cosmetic Products: | |||
| 0.08 mg/kg/day (IFRA, 2001) | |||
| 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: 3 | |||
| Click here to view publication 3 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 5.20000 | |
| beverages(nonalcoholic): | - | 1.60000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | 89.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 3.40000 | |
| fruit ices: | - | 3.40000 | |
| gelatins / puddings: | - | 5.80000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 7.60000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | 10.00000 | |
| meat products: | - | - | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | 10.00000 | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
Safety references
| EPI System: View |
| Chemical Carcinogenesis Research Information System:Search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):79-77-6 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :6433147 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 3082 |
| WGK Germany:2 |
| (E)-4-[(5R)-5,6,6-trimethylcyclohexen-1-yl]but-3-en-2-one |
| Chemidplus:0000079776 |
| RTECS:EN0500000 for cas# 79-77-6 |