2,6-dimethoxy-4-vinyl phenol
2,6-dimethoxy-4-vinylphenol
Identification
| Name | 2,6-dimethoxy-4-vinyl phenol |
| IUPAC | 4-ethenyl-2,6-dimethoxyphenol |
| CAS Number | 28343-22-8 |
| FDA UNII | ZB5OK5EX8B |
| Molecular Formula | C10 H12 O3 |
| Molecular Weight | 180.20324000 |
| CoE Number | 11229 |
Regulatory
| DG SANTE Food Flavourings | 04.061 2,6-dimethoxy-4-vinylphenol |
Physical Properties
| Appearance | colorless solid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 133.00 to 135.00 °C. @ 760.00 mm Hg |
| Boiling Point | 314.00 to 315.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.002000 mmHg @ 25.00 °C. (est) |
| Flash Point | 259.00 °F. TCC ( 126.11 °C. ) |
| logP (o/w) | 2.606 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Organoleptic Properties
| Odor Description | at 10.00 % in dipropylene glycol. |
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavoring agents |
| Recommendation for 2,6-dimethoxy-4-vinyl phenol usage levels up to | not for fragrance use. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 1.20 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 420 (μg/person/day) |
| Threshold of Concern | 1800 (μg/person/day) |
| Structure Class | I |
| Dairy products, excluding products of category 02.0 (01.0) | 0.50000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 0.20000 |
| Edible ices, including sherbet and sorbet (03.0) | 0.50000 |
| Processed fruit (04.1) | 0.40000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 1.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 0.20000 |
| Bakery wares (07.0) | 2.00000 |
| Meat and meat products, including poultry and game (08.0) | 0.20000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 0.20000 |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | 0.30000 |
| Foodstuffs intended for particular nutritional uses (13.0) | 0.50000 |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 0.20000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 1.00000 |
| Ready-to-eat savouries (15.0) | 2.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 0.40000 |
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Potential Uses
Natural Occurrence
Synonyms
canolol
2,6-
dimethoxy-4-vinylphenol
4-
ethenyl-2,6-dimethoxyphenol
phenol, 4-ethenyl-2,6-dimethoxy-
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Cold-pressed and hot-pressed rapeseed oil: The effects of roasting and seed moisture on the antioxi- dant activity, canolol, and tocopherol level.
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Dehulling and microwave pretreatment effects on the physicochemical composition and antioxidant capacity of virgin rapeseed oil.
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Mechanical hulling and thermal pre-treatment effects on rapeseed oil antioxidant capacity and related lipophilic and hydrophilic bioactive compounds.
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Antioxidant (Tocopherol and Canolol) Content in Rapeseed Oil Obtained from Roasted Yellow-Seeded Brassica napus.
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The effect of microwave pretreatment of seeds on the stability and degradation kinetics of phenolic compounds in rapeseed oil during long-term storage.
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Potential of endophytic fungus Phomopsis liquidambari for transformation and degradation of recalcitrant pollutant sinapic acid.
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Flavoromics approach in monitoring changes in volatile compounds of virgin rapeseed oil caused by seed roasting.
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Changes in 4-vinylsyringol and other phenolics during rapeseed oil refining.
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Canolol inhibits gastric tumors initiation and progression through COX-2/PGE2 pathway in K19-C2mE transgenic mice.
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Value-added potential of expeller-pressed canola oil refining: characterization of sinapic acid derivatives and tocopherols from byproducts.
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Effect of seed roasting on canolol, tocopherol, and phospholipid contents, Maillard type reactions, and oxidative stability of mustard and rapeseed oils.
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Influence of microwaves treatment of rapeseed on phenolic compounds and canolol content.
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Endogenous Phenolics in Hulls and Cotyledons of Mustard and Canola: A Comparative Study on Its Sinapates and Antioxidant Capacity.
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Protection from inflammatory bowel disease and colitis-associated carcinogenesis with 4-vinyl-2,6-dimethoxyphenol (canolol) involves suppression of oxidative stress and inflammatory cytokines.
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Anticancer effects of 4-vinyl-2,6-dimethoxyphenol (canolol) against SGC-7901 human gastric carcinoma cells.
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Isolation and identification of a potent radical scavenger (canolol) from roasted high erucic mustard seed oil from Nepal and its formation during roasting.
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Protective effect of canolol from oxidative stress-induced cell damage in ARPE-19 cells via an ERK mediated antioxidative pathway.
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Canolol: a promising chemical agent against oxidative stress.
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Therapeutic strategies by modulating oxygen stress in cancer and inflammation.
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4-Vinyl-2,6-dimethoxyphenol (canolol) suppresses oxidative stress and gastric carcinogenesis in Helicobacter pylori-infected carcinogen-treated Mongolian gerbils.
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Isolation, identification, and structure of a potent alkyl-peroxyl radical scavenger in crude canola oil, canolol.
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Antioxidative and antimutagenic activities of 4-vinyl-2,6-dimethoxyphenol (canolol) isolated from canola oil.