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beta-ionol
beta-Ionol is a bicyclic floral fragrance and flavor compound with woody, berry, and violet notes, used primarily in perfumery and flavor formulations.
General Material Description
Beta-ionol, also known chemically as 4-(2,6,6-trimethyl-1-cyclohexenyl)but-3-en-2-ol, is an organic bicyclic alcohol classified within monoterpenoid-related fragrance compounds. It appears as a clear substance with a molecular formula of C13H22O and displays a characteristic floral scent profile encompassing sweet, woody, berry-like, violet, and balsamic nuances. This compound is recognized under various synonyms including 2-hydroxy-beta-ionone and beta-ionol itself, validated by identifiers such as CAS number 22029-76-1. Beta-ionol is typically sourced via synthetic routes or isolated in minor amounts from natural materials like champaca absolute, grape, and red raspberry fruits. It serves as a valued component in flavor and fragrance formulations, lending complexity and depth to aromatic blends. More chemical information can be found on external resources like PubChem.
Occurrence, Applicability & Potential Uses
Beta-ionol naturally occurs in certain floral and fruit sources, including champaca absolute, grape, and red raspberry fruits. Its presence in these botanical materials contributes to their distinctive scent and flavor characteristics. The compound is widely used as a flavor and fragrance agent in various industrial applications. In perfumery, beta-ionol imparts a medium-strength floral scent with woody and balsamic undertones, contributing to compositions involving violet, berry, and tropical notes. It also enhances flavor profiles by adding floral and fruity nuances, especially to stone fruits, blueberries, strawberries, and pineapple. Regulatory frameworks such as FEMA (US) govern the safe use levels of beta-ionol in flavorings, supported by EFSA (EU) evaluations. Its inclusion in formulations follows recommended standards to ensure consistency and safety in consumer products.
Physico-Chemical Properties Summary
Beta-ionol is a relatively hydrophobic bicyclic alcohol with a molecular weight of approximately 194.3 g/mol. Its specific gravity ranges from 0.923 to 0.93 at 25 B0C, indicating a density slightly less than water. The refractive index spans from 1.496 to 1.502 at 20 B0C, relevant for analytical verification and quality control. This compound exhibits a low vapor pressure of 0.000431 mmHg at 25 B0C, reflecting moderate volatility suitable for fragrance persistence. The estimated logP value of 4.059 signifies high lipophilicity, influencing its solubility and interaction within both cosmetic and flavor matrices. Beta-ionol is soluble in alcohol and has limited solubility in water, measured around 16.29 mg/L at 25 B0C. Its flash point of approximately 93 B0C (200 B0F) supports safe handling under typical industrial conditions. These physicochemical properties contribute to its performance and stability in formulated products.
FAQ
What is beta-ionol and what are its sensory characteristics?
Beta-ionol is an organic bicyclic alcohol used primarily as a flavor and fragrance compound. It is characterized by a medium-strength floral aroma with sweet, woody, berry, violet, and balsamic nuances. Its flavor profile includes floral violet-like notes, complemented by fruity and powdery aspects. These sensory attributes make beta-ionol valuable in perfumery and flavor formulations, particularly enhancing fruit and floral compositions.
Where is beta-ionol found naturally, and how is it used in industry?
Beta-ionol occurs naturally in floral and fruit sources such as champaca absolute, grape, and red raspberry fruit. Industrially, it is utilized as a flavor and fragrance agent to impart floral, woody, berry, and violet notes. It is suitable for use in diverse products including perfumery, baked goods, beverages, confectionery, and dairy items. Regulatory standards from FEMA (US) and EFSA (EU) define its permissible concentrations and ensure safe application.
What are the regulatory considerations and safety data associated with beta-ionol?
Beta-ionol is regulated under FEMA (US), IFRA (Global), and EFSA (EU) frameworks that establish maximum usage levels for flavor and fragrance applications. Its safety profile indicates low acute toxicity with oral and dermal LD50 values above 5000 mg/kg in animal studies. The compound is classified as harmful if swallowed and requires standard precautions such as avoiding skin and eye contact. IFRA guidelines recommend usage levels up to 8% in fragrance concentrates, reflecting its safety margin. Safety data sheets and assessments are available from authoritative sources to guide handling and formulation.
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 |
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): | HMDB36820 |
| FooDB: | FDB015768 |
| Export Tariff Code: | 2906.19.5000 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | beta-ionol |
| Trivial Name | β-Ionol |
| Short Description | 4-(2,2,6-trimethyl-1-cyclohexenyl)but-3-en-2-ol |
| Formula | C13 H22 O |
| CAS Number | 22029-76-1 |
| FEMA Number | 3625 |
| Flavis Number | 2.106 |
| ECHA Number | 244-735-7 |
| FDA UNII | Search |
| Nikkaji Number | J146.841C |
| Beilstein Number | 1866761 |
| MDL | MFCD00036597 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 392 beta-ionol |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 22029-76-1 ; BETA-IONOL |
| Synonyms |
|
Suppliers
| Bedoukian Research | BOC Sciences |
| Lluch Essence | Penta International |
| Santa Cruz Biotechnology | Sigma-Aldrich |
| Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 194.31753540039 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.68 to 7.739 |
| Refractive Index | 1.496 to 1.502 @ 20 °C |
| Vapor Pressure | 0.000431 mmHg @ 25 °C |
| Vapor Density | 1 |
| Flash Point TCC Value | 93.33 °C TCC |
| logP (o/w) | 4.059 est |
| Solubility | |
| alcohol | Yes |
| water, 16.29 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Floral | |
| sweet, herbal, floral, violet, tropical, balsamic, woody, berry, powdery, fruity | |
| Odor strength | medium |
| Substantivity | 168 hour(s) at 100.00 % |
| Luebke, William tgsc, (1995) | At 100.00 %. sweet herbal floral violet tropical balsam woody |
| Mosciano, Gerard P&F 19, No. 2, 55, (1994) | Sweet, woody, berry, powdery, floral and fruity |
| Flavor Type: Floral | |
| floral, violet, fruity, woody, berry, powdery | |
| Mosciano, Gerard P&F 19, No. 2, 55, (1994) | At 20.00 ppm. Floral violet-like, fruity, woody, berry with powdery nuances |
| Used for pitty note in stone fruits. Also adds body to blueberry, strawberry and pineapple flavors. | Woody berry |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Balsam , Blueberry , Hay new mown hay , Licorice , Pineapple , Raspberry , Strawberry , Tobacco , Violet , Woody |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xn - Harmful. | |
| R 22 - Harmful if swallowed. S 02 - Keep out of the reach of children. S 20/21 - When using do not eat, drink or smoke. 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. | |
| 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 LDLo 5000 mg/kg Food and Chemical Toxicology. Vol. 26, Pg. 361, 1988. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Chemical Toxicology. Vol. 26, Pg. 361, 1988. | |
| 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 beta-ionol usage levels up to: | |||
| 8.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.73 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.10 (μg/capita/day) | ||
| Structure Class: | I | ||
| 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: 12 | |||
| Click here to view publication 12 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 3.00000 | |
| beverages(nonalcoholic): | - | 1.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | 5.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | 2.00000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 1.50000 | |
| fruit ices: | - | 1.50000 | |
| gelatins / puddings: | - | 2.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 4.00000 | |
| imitation dairy: | - | 1.50000 | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | 2.00000 | |
| meat products: | - | - | |
| milk products: | - | 1.50000 | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | 2.50000 | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
| Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i). | |||
| Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm. | |||
| average usage mg/kg | maximum usage mg/kg | ||
| Dairy products, excluding products of category 02.0 (01.0): | 1.00000 | 5.00000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 8.00000 | 50.00000 | |
| Edible ices, including sherbet and sorbet (03.0): | 2.00000 | 10.00000 | |
| Processed fruit (04.1): | 1.00000 | 5.00000 | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | 1.00000 | 5.00000 | |
| Confectionery (05.0): | 5.00000 | 20.00000 | |
| Chewing gum (05.3): | 20.00000 | 100.00000 | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 1.00000 | 5.00000 | |
| Bakery wares (07.0): | 5.00000 | 20.00000 | |
| Meat and meat products, including poultry and game (08.0): | 1.00000 | 5.00000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 1.00000 | 5.00000 | |
| Eggs and egg products (10.0): | 1.00000 | 5.00000 | |
| Sweeteners, including honey (11.0): | 1.00000 | 5.00000 | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 5.00000 | 20.00000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | - | - | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 1.00000 | 5.00000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 1.00000 | 5.00000 | |
| Ready-to-eat savouries (15.0): | 1.00000 | 5.00000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 1.00000 | 5.00000 | |
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 213: alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.7 of FGE.19 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 9, Revision 5 (FGE.09Rev5): Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical group 8 and 30, and an ester of a phenol derivative from chemical group 25 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 87, Revision 2 (FGE.87Rev2): Consideration of bicyclic secondary alcohols, ketones and related esters evaluated by JECFA (63rd meeting) structurally related to bicyclic secondary alcohols, ketones and related esters evaluated by EFSA in FGE.47Rev1 (2008) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 213, Revision 2 (FGE.213Rev2): Consideration of genotoxic potential for a,ß-unsaturated alicyclic ketones and precursors from chemical subgroup 2.7 of FGE.19 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):22029-76-1 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5373729 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| 4-(2,6,6-trimethyl-1-cyclohexenyl)but-3-en-2-ol |
| Chemidplus:0022029761 |
| RTECS:EM9630000 for cas# 22029-76-1 |