2,6-dimethoxy-4-vinyl phenol
2,6-dimethoxy-4-vinylphenol
 
Notes:
None found
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      Product(s):
      28343-22-8 Phenol,4-ethenyl-2,6-dimethoxy-
       
  • CSA
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CAS Number: 28343-22-8Picture of molecule3D/inchi
FDA UNII: ZB5OK5EX8B
CoE Number: 11229
XlogP3-AA: 2.30 (est)
Molecular Weight: 180.20324000
Formula: C10 H12 O3
NMR Predictor: Predict (works with chrome or firefox)
Category: flavoring agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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DG SANTE Food Flavourings: 04.061  2,6-dimethoxy-4-vinylphenol
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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
 water, 947.8 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
 
Odor Type: animal
 
Odor Strength: medium ,
recommend smelling in a 10.00 % solution or less
 
 phenolic  animal  leathery  
Odor Description:
at 10.00 % in dipropylene glycol. 
phenolic animal leather
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
Phenol,4-ethenyl-2,6-dimethoxy-
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the CSA
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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
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Safety in Use Information:
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
 
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/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 0.500002.50000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 0.200001.00000
Edible ices, including sherbet and sorbet (03.0): 0.500002.50000
Processed fruit (04.1): 0.400002.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 1.000005.00000
Chewing gum (05.0): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 0.200001.00000
Bakery wares (07.0): 2.0000010.00000
Meat and meat products, including poultry and game (08.0): 0.200001.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 0.200001.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 0.300001.50000
Foodstuffs intended for particular nutritional uses (13.0): 0.500002.50000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 0.200001.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 1.000005.00000
Ready-to-eat savouries (15.0): 2.0000010.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 0.400002.00000
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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):
Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 22 (FGE.22): Ring-substituted phenolic substances from chemical groups 21 and 25 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf
Flavouring Group Evaluation 58 (FGE.58) Consideration of phenol derivatives evaluated by JECFA (55th meeting) structurally related to ring substituted phenolic substances evaluated by EFSA in FGE.22 (2006) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 22, Revision 1 (FGE.22Rev1): Ring-substituted phenolic substances from chemical groups 21 and 25
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 : 35960
National Institute of Allergy and Infectious Diseases: Data
 4-ethenyl-2,6-dimethoxyphenol
Chemidplus: 0028343228
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References:
 4-ethenyl-2,6-dimethoxyphenol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 35960
Pubchem (sid): 135212462
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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
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
For Odor
amber
amber
 ambrette seed oil CO2 extractFL/FR
alpha-ambrinolFL/FR
6-tert-butyl-meta-cresolFL/FR
 castoreum liquidFL/FR
 castoreum resinoidFL/FR
 castoreum tinctureFL/FR
 civet absoluteFL/FR
para-cresyl caprylateFL/FR
para-cresyl isobutyrateFL/FR
para-cresyl phenyl acetateFL/FR
 indoleFL/FR
6-methyl quinolineFL/FR
para-methyl tetrahydroquinolineFL/FR
 piperidineFL/FR
 skatoleFL/FR
1-oxaspiro-4,7-dodecaneFR
anisic
ortho-acetanisoleFL/FR
balsamic
 amyl phenyl acetateFL/FR
sumatra benzoin absoluteFL/FR
 opoponax oil (balsamodendron kafal)FL/FR
camphoreous
dextro-camphorFL/FR
chocolate
isoamyl phenyl acetateFL/FR
 vanillyl ethyl etherFL/FR
coumarinic
 phthalideFL/FR
creamy
para-vanillyl alcoholFL/FR
ethereal
 propyl valerateFL/FR
fatty
delta-juniper lactoneFL/FR
floral
alpha-amyl cinnamyl acetateFL/FR
 benzyl alcoholFL/FR
 cananga oilFL/FR
 citronellolFL/FR
para-cresyl acetateFL/FR
 dimethyl anthranilateFL/FR
 dimethyl octanolFL/FR
ortho-methyl acetophenoneFL/FR
(E)-2,5,9-trimethyl-4,9-decadien-1-alFR
fruity
 ethyl 3-hydroxyhexanoateFL/FR
 linalyl hexanoateFL/FR
 osmanthus flower absoluteFL/FR
meta-tolualdehydeFL/FR
para-tolualdehydeFL/FR
green
 diphenyl oxideFL/FR
 phenoxyacetaldehyde 50% in benzyl alcoholFR
 seaweed absolute (fucus vesiculosus et serratus)FL/FR
 valerian rhizome oil CO2 extract chinaFL/FR
herbal
 saffron indenoneFL/FR
 valerian rhizome oilFL/FR
 valerian rhizome oil chinaFL/FR
 yerba mate absoluteFL/FR
honey
 phenyl pyruvic acidFL/FR
leathery
 castoreum absoluteFL/FR
medicinal
2,6-xylenolFL/FR
minty
 piperitenoneFL/FR
mossy
 sea resorcylateFR
 veramoss (IFF)FR
musk
(Z)-civet decenoneFL/FR
 juniper lactoneFL/FR
dextro,laevo-musconeFL/FR
 musk dimethyl indaneFL/FR
omega-pentadecalactoneFL/FR
nutty
2,3-dimethyl pyrazineFL/FR
 nutty cyclohexenoneFL/FR
phenolic
para-cresolFL/FR
ortho-cresyl isobutyrateFL/FR
2,3-dimethyl benzofuranFL/FR
para-alpha-dimethyl styreneFL/FR
ortho-guaiacolFL/FR
2'-hydroxyacetophenoneFL/FR
 methyl benzoateFL/FR
4-methyl-2,6-dimethoxyphenolFL/FR
4-propyl phenolFL/FR
2-propyl phenolFL/FR
4-vinyl phenolFL/FR
2,3-xylenolFL/FR
2,5-xylenolFL/FR
smoky
4-ethyl phenolFL/FR
 pyroligneous acidsFL/FR
spicy
 clove bud absoluteFL/FR
 cuminyl alcoholFL/FR
4-ethyl guaiacolFL/FR
4-methyl guaiacolFL/FR
(E,E)-piperineFL/FR
 zingeroneFL/FR
tobacco
para-cresyl isovalerateFL/FR
3-ethyl pyridineFL/FR
 methyl benzoxoleFL/FR
tropical
 genet absoluteFL/FR
vanilla
ortho-dimethyl hydroquinoneFL/FR
woody
 cistus twig/leaf oil molecular distilledFL/FR
 guaiacyl acetateFL/FR
 methyl cedryl ketoneFL/FR
 spikenard oilFL/FR
beta-thujaplicinFR
 
For Flavor
 
No flavor group found for these
 amyl phenyl acetateFL/FR
para-anisic acidFL
6-tert-butyl-meta-cresolFL/FR
ortho-cresyl isobutyrateFL/FR
2,4-dihydroxybenzoic acidFL
ortho-dimethyl hydroquinoneFL/FR
2-furfurylidene butyraldehydeFL
 linalyl hexanoateFL/FR
3-methyl crotonic acidFL
4-methyl cyclohexanoneFL
4-methyl salicylaldehydeFL
para-methyl tetrahydroquinolineFL/FR
 piperidineFL/FR
 piperitenoneFL/FR
2-propyl phenolFL/FR
4-propyl phenolFL/FR
 propyl valerateFL/FR
para-salicylic acidFL
 seaweed absolute (fucus vesiculosus et serratus)FL/FR
 skatoleFL/FR
 spikenard oilFL/FR
amber
 ambrette seed oil CO2 extractFL/FR
alpha-ambrinolFL/FR
animal
 castoreum liquidFL/FR
 castoreum resinoidFL/FR
 castoreum tinctureFL/FR
 civet absoluteFL/FR
para-cresyl caprylateFL/FR
 indoleFL/FR
6-methyl quinolineFL/FR
anisic
ortho-methyl acetophenoneFL/FR
aromatic
para-cresyl acetateFL/FR
para-cresyl isobutyrateFL/FR
balsamic
 opoponax oil (balsamodendron kafal)FL/FR
burnt
2,6-xylenolFL/FR
caramellic
3-ethyl pyridineFL/FR
chemical
2,3-dimethyl benzofuranFL/FR
coumarinic
 phthalideFL/FR
creamy
para-vanillyl alcoholFL/FR
earthy
alpha-amyl cinnamyl acetateFL/FR
fatty
 dimethyl octanolFL/FR
delta-juniper lactoneFL/FR
fishy
3-penten-2-oneFL
floral
isoamyl phenyl acetateFL/FR
 cananga oilFL/FR
 citronellolFL/FR
fruity
 benzyl alcoholFL/FR
 dimethyl anthranilateFL/FR
 ethyl 3-hydroxyhexanoateFL/FR
 osmanthus flower absoluteFL/FR
meta-tolualdehydeFL/FR
 valerian rhizome oilFL/FR
 valerian rhizome oil chinaFL/FR
 valerian rhizome oil CO2 extract chinaFL/FR
green
 diphenyl oxideFL/FR
hay
 genet absoluteFL/FR
herbal
 saffron indenoneFL/FR
 yerba mate absoluteFL/FR
leathery
 castoreum absoluteFL/FR
meaty
2,6-dimethyl thiophenolFL
ortho-thioguaiacolFL
medicinal
dextro-camphorFL/FR
musk
(Z)-civet decenoneFL/FR
 juniper lactoneFL/FR
dextro,laevo-musconeFL/FR
 musk dimethyl indaneFL/FR
musty
2-ethoxythiazoleFL
2,5-xylenolFL/FR
naphthyl
2'-hydroxyacetophenoneFL/FR
nutty
2,3-dimethyl pyrazineFL/FR
 methyl benzoxoleFL/FR
 nutty cyclohexenoneFL/FR
phenolic
para-cresolFL/FR
para-cresyl isovalerateFL/FR
para-cresyl phenyl acetateFL/FR
 methyl benzoateFL/FR
4-methyl-2,6-dimethoxyphenolFL/FR
 phenyl pyruvic acidFL/FR
4-vinyl phenolFL/FR
2,3-xylenolFL/FR
powdery
ortho-acetanisoleFL/FR
roasted
 ethyl 3-(furfuryl thio) propionateFL
rummy
 vanillyl ethyl etherFL/FR
smoky
4-ethyl phenolFL/FR
 pyroligneous acidsFL/FR
sour
3-methyl valeric acidFL
spicy
sumatra benzoin absoluteFL/FR
 clove bud absoluteFL/FR
 cuminyl alcoholFL/FR
para-alpha-dimethyl styreneFL/FR
4-methyl guaiacolFL/FR
(E,E)-piperineFL/FR
para-tolualdehydeFL/FR
 zingeroneFL/FR
vanilla
omega-pentadecalactoneFL/FR
woody
 cistus twig/leaf oil molecular distilledFL/FR
4-ethyl guaiacolFL/FR
ortho-guaiacolFL/FR
 guaiacyl acetateFL/FR
 methyl cedryl ketoneFL/FR
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 beer - up to 0.03 mg/kg
Search  PMC Picture
 coffee - 1.8 mg/kg
Search  PMC Picture
 wort - 0.05 mg/kg
Search  Picture
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Synonyms:
 canolol
2,6-dimethoxy-4-vinylphenol
4-ethenyl-2,6-dimethoxyphenol
 phenol, 4-ethenyl-2,6-dimethoxy-
Synonyms   Articles   Notes   Search   Top
Articles:
PubMed: Cold-pressed and hot-pressed rapeseed oil: The effects of roasting and seed moisture on the antioxi- dant activity, canolol, and tocopherol level.
PubMed: Dehulling and microwave pretreatment effects on the physicochemical composition and antioxidant capacity of virgin rapeseed oil.
PubMed: Mechanical hulling and thermal pre-treatment effects on rapeseed oil antioxidant capacity and related lipophilic and hydrophilic bioactive compounds.
PubMed: Antioxidant (Tocopherol and Canolol) Content in Rapeseed Oil Obtained from Roasted Yellow-Seeded Brassica napus.
PubMed: The effect of microwave pretreatment of seeds on the stability and degradation kinetics of phenolic compounds in rapeseed oil during long-term storage.
PubMed: Potential of endophytic fungus Phomopsis liquidambari for transformation and degradation of recalcitrant pollutant sinapic acid.
PubMed: Flavoromics approach in monitoring changes in volatile compounds of virgin rapeseed oil caused by seed roasting.
PubMed: Changes in 4-vinylsyringol and other phenolics during rapeseed oil refining.
PubMed: Canolol inhibits gastric tumors initiation and progression through COX-2/PGE2 pathway in K19-C2mE transgenic mice.
PubMed: Value-added potential of expeller-pressed canola oil refining: characterization of sinapic acid derivatives and tocopherols from byproducts.
PubMed: Effect of seed roasting on canolol, tocopherol, and phospholipid contents, Maillard type reactions, and oxidative stability of mustard and rapeseed oils.
PubMed: Influence of microwaves treatment of rapeseed on phenolic compounds and canolol content.
PubMed: Endogenous Phenolics in Hulls and Cotyledons of Mustard and Canola: A Comparative Study on Its Sinapates and Antioxidant Capacity.
PubMed: Protection from inflammatory bowel disease and colitis-associated carcinogenesis with 4-vinyl-2,6-dimethoxyphenol (canolol) involves suppression of oxidative stress and inflammatory cytokines.
PubMed: Anticancer effects of 4-vinyl-2,6-dimethoxyphenol (canolol) against SGC-7901 human gastric carcinoma cells.
PubMed: Isolation and identification of a potent radical scavenger (canolol) from roasted high erucic mustard seed oil from Nepal and its formation during roasting.
PubMed: Protective effect of canolol from oxidative stress-induced cell damage in ARPE-19 cells via an ERK mediated antioxidative pathway.
PubMed: Canolol: a promising chemical agent against oxidative stress.
PubMed: Therapeutic strategies by modulating oxygen stress in cancer and inflammation.
PubMed: 4-Vinyl-2,6-dimethoxyphenol (canolol) suppresses oxidative stress and gastric carcinogenesis in Helicobacter pylori-infected carcinogen-treated Mongolian gerbils.
PubMed: Isolation, identification, and structure of a potent alkyl-peroxyl radical scavenger in crude canola oil, canolol.
PubMed: Antioxidative and antimutagenic activities of 4-vinyl-2,6-dimethoxyphenol (canolol) isolated from canola oil.
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