Articles:
2-(2-hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone
Notes:
Constit. of wine
Wine lactone is a pleasant smelling compound found naturally in apples, orange juice, grapefruit juice, orange essential oil, clementine peel oil and various grape wines. Used as a food additive [EAFUS]
| CAS Number: | 57743-63-2 |  3D/inchi
|
| Nikkaji Web: | J892.295K | |
| XlogP3-AA: | 1.70 (est) | |
| Molecular Weight: | 166.21998000 | |
| Formula: | C10 H14 O2 | |
| NMR Predictor: | Predict (works with chrome or firefox) | |
| EFSA/JECFA Comments: | Isomeric composition: 81-84% (3aS,7aR), 16-19% (3aR, 7aS) | |
Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
| Google Scholar: | Search |
| Google Books: | Search |
| Google Scholar: with word "volatile" | Search |
| Google Scholar: with word "flavor" | Search |
| Google Scholar: with word "odor" | Search |
| Perfumer and Flavorist: | Search |
| Google Patents: | Search |
| US Patents: | Search |
| EU Patents: | Search |
| Pubchem Patents: | Search |
| PubMed: | Search |
| NCBI: | Search |
| JECFA Food Flavoring: | 2223 2-(2-hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone |
| DG SANTE Food Flavourings: | 10.057 3a,4,5,7a-tetrahydro-3,6-dimethyl benzofuran-2(3H)-one |
| FEMA Number: | 4140 2-(2-hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone |
| FDA: | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF): | 57743-63-2 ; 2-(2-HYDROXY-4-METHYL-3-CYCLOHEXENYL)PROPIONIC ACID GAMMA-LACTONE |
Physical Properties:
| Appearance: | colorless to pale yellow clear liquid (est) |
| Assay: | 95.00 to 100.00 % |
| Food Chemicals Codex Listed: | No |
| Specific Gravity: | 1.05300 to 1.05900 @ 25.00 °C. |
| Pounds per Gallon - (est).: | 8.762 to 8.812 |
| Refractive Index: | 1.49400 to 1.50000 @ 20.00 °C. |
| Melting Point: | 13.00 °C. @ 760.00 mm Hg |
| Boiling Point: | 231.00 °C. @ 760.00 mm Hg |
| Vapor Pressure: | 0.003000 mmHg @ 25.00 °C. (est) |
| Flash Point: | 239.00 °F. TCC ( 115.00 °C. ) |
| logP (o/w): | 1.634 (est) |
| Soluble in: | |
| alcohol | |
| water, 1834 mg/L @ 25 °C (est) | |
| Insoluble in: | |
| water | |
Organoleptic Properties:
| Odor Type: spicy | |
| Odor Strength: | medium , recommend smelling in a 1.00 % solution or less |
| sweet spicy woody | |
| Odor Description: at 1.00 % in propylene glycol. | sweet spicy woody |
| Odor and/or flavor descriptions from others (if found). | |
Cosmetic Information:
| None found |
Suppliers:
| Axsyn |
| For experimental / research use only. |
| 2-(2-HYDROXY-4-METHYL-3-CYCLOHEXENYL)PROPIONICACIDGAMMA-LACTONE |
| Parchem |
| wine lactone |
Safety Information:
| 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 | ||
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice | |||
| Recommendation for wine lactone usage levels up to: | |||
| 0.5000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.012 (μg/capita/day) | ||
| Structure Class: | III | ||
| 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: 22 | |||
| Click here to view publication 22 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 1.00000 | 5.00000 | |
| beverages(nonalcoholic): | 0.50000 | 5.00000 | |
| beverages(alcoholic): | 2.00000 | 10.00000 | |
| breakfast cereal: | 2.00000 | 10.00000 | |
| cheese: | 0.50000 | 2.00000 | |
| chewing gum: | 1.00000 | 10.00000 | |
| condiments / relishes: | 5.00000 | 20.00000 | |
| confectionery froastings: | 2.00000 | 10.00000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | 0.50000 | 5.00000 | |
| fruit ices: | - | - | |
| gelatins / puddings: | 2.00000 | 10.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | 1.00000 | 10.00000 | |
| imitation dairy: | 1.00000 | 10.00000 | |
| instant coffee / tea: | 1.00000 | 10.00000 | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | 0.50000 | 2.00000 | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | 50.00000 | 200.00000 | |
| snack foods: | - | - | |
| soft candy: | 2.00000 | 10.00000 | |
| 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 217: alpha,beta-Unsaturated ketones and precursors from chemical subgroup 4.1 of FGE.19: Lactones[1] View page or View pdf | |
| Scientific Opinion on Flavouring Group Evaluation 217, Revision 1 (FGE.217Rev1). Consideration of genotoxic potential for a,ß-unsaturated ketones and precursors from chemical subgroup 4.1 of FGE.19: Lactones View page or View pdf | |
| Scientific Opinion on Flavouring Group Evaluation 217 Revision 2 (FGE.217Rev2), consideration of genotoxic potential for a,ß-unsaturated ketones and precursors from chemical subgroup 4.1 of FGE.19: lactones View page or View pdf | |
| EPI System: | View |
| AIDS Citations: | Search |
| Cancer Citations: | Search |
| Toxicology Citations: | Search |
| EPA ACToR: | Toxicology Data |
| EPA Substance Registry Services (SRS): | Registry |
| Laboratory Chemical Safety Summary : | 6427076 |
| National Institute of Allergy and Infectious Diseases: | Data |
| WGK Germany: | 3 |
| 3,6-dimethyl-3a,4,5,7a-tetrahydro-3H-1-benzofuran-2-one | |
| Chemidplus: | 0057743632 |
References:
| Leffingwell: | Chirality or Article |
| 3,6-dimethyl-3a,4,5,7a-tetrahydro-3H-1-benzofuran-2-one | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 6427076 |
| Pubchem (sid): | 135343087 |
| 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): | HMDB29691 |
| FooDB: | FDB009603 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
| EFSA Update of results on the monitoring of furan levels in food: | Read Report |
| EFSA Previous report: Results on the monitoring of furan levels in food: | Read Report |
| EFSA Report of the CONTAM Panel on provisional findings on furan in food: | Read Report |
Potential Blenders and core components note
| None Found | ||
Potential Uses:
| None Found |
Occurrence (nature, food, other): note
| apple fruit Search PMC Picture | |
| clementine peel oil Search Trop Picture | |
| orange fruit juice Search Trop Picture | |
| orange oil Search Trop Picture | |
| wine Search Picture |
Synonyms:
| 2(3H)- | benzofuranone, 3,6-dimethyl-3a,4,5,7a-tetrahydro- |
| 2(3H)- | benzofuranone, 3a,4,5,7a-tetrahydro-3,6-dimethyl- |
| 3,6- | dimethyl-3a,4,5,7a-tetrahydro-1-benzofuran-2(3H)-one |
| 3,6- | dimethyl-3a,4,5,7a-tetrahydro-3H-1-benzofuran-2-one |
| 2-(2- | hydroxy-4-methyl-3-cyclohexenyl) propionic acid gamma-lactone |
| 2-(2- | hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone |
| 3a,4,5,7a- | tetrahydro-3,6-dimethyl benzofuran-2(3H)-one |
| 3a,4,5,7a- | tetrahydro-3,6-dimethyl-2(3H)-benzofuranone |
| tetrahydro-3,6-dimethyl-2(3H)-benzofuranone, 3a,4,5,7a |