Basic information
- CAS
7786-61-0- Standard SMILES
C=Cc1ccc(O)c(OC)c1- InChIKey
YOMSJEATGXXYPX-UHFFFAOYSA-N- Molecular formula
- C9H10O2
- Average molar mass
- 150.17 g/mol
- Monoisotopic mass
- 150.06807956
Names & identifiers
- Preferred name
- 4-Vinylguaiacol
- IUPAC
- 4-ethenyl-2-methoxyphenol
- English name
- 4-Hydroxy-3-methoxystyrene
- Molecular formula
- C9H10O2
- Molecular weight
- 150.17
Names & synonyms
2-Methoxy-4-vinylphenol7786-61-04-vinylguaiacolp-Vinylguaiacol4-Hydroxy-3-methoxystyrene4-ETHENYL-2-METHOXYPHENOLPhenol, 4-ethenyl-2-methoxy-o-methoxy-p-vinylphenol4-vinyl-2-methoxyphenolpara-vinylguaiacolGuaiacol, 4-vinyl-Phenol, 2-methoxy-4-vinyl-
Show more names
FEMA 26752-Methoxy-4-vinylphenol (4-vinylguaiacol)VINYL GUAIACOLp-Vinyl guaicol
4-Hydroxy-3-methoxyvinylbenzene3-Methoxy-4-hydroxystyreneFEMA No. 2675Varamol 106DTXSID70525292M4VPDA069CTH0O4-hydroxy-3-methoxyphenylethene
Database identifiers
- CAS
7786-61-0- PubChem CID
- 332
- DTXSID
DTXSID7052529- ChEMBL
CHEMBL1232595- ChEBI
CHEBI:42438- UNII
- DA069CTH0O
- EC Number
- 232-101-2
- Nikkaji
- J134.783G
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 29.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 134
Physicochemical properties
- Melting point
- 25 · 25-29°C
- Boiling point
- 224 °C · 224 °C(lit.)
- Density
- 1.11 g/mL · 1.11 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.582(lit.)
- FEMA
- 2675 · 2675 | 2-METHOXY-4-VINYLPHENOL
- FLAVIS Number
- 4.009 · 04.009 | 2-Methoxy-4-vinylphenol
- Flash point
- 230 °F · >230 °F
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
- pka
- 10 · 10.00±0.31(Predicted)
- form
- Liquid
- color
- Colourless to Off-White Oil
- Odor
- 0.1 % · at 0.10 % in dipropylene glycol. sweet spicy clove carnation phenolic peppery smoky woody powdery
- Odor Type
- spicy
- biological source
- synthetic
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- SL8205000
- ridadr
- UN1760
- hs_code
- 29095000
- risk_code
- 36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- Xi
- safety_code
- 26-36
- hazard_class
- 8
- Storage Class
- 8B - Non-combustible corrosive hazardous materials
- Hazard statements
- H314
- Limited Quantities
- 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- Hazard Classifications
- Eye Dam. 1Skin Corr. 1B
- Precautionary statements
- P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363
Chemistry & industry
Applications
OccurrenceReported found among the steam-distillable phenols from the alcoholic fermentation of cereal grains, especially corn; probably formed from ferulic acid. Reported found in tobacco, beans, coffee, malt, apple, grapefruit juice, grapes, raspberry, strawberry, asparagus, kohlrabi, carrot, celery, tomato, rye bread, smoked fish, cured pork, beer, cognac, rum, cider, sherry, grape wines, coffee, tea, peanut, popcorn,soybean, passion fruit, beans,starfruit,sesame seed, mango, cauliflower, tamarind, fig, corianderseed, rice, quince, rhubarb, dill, lovage root, corn oil, sweet corn, malt, wort, Texas sage, okra, cuttlefish and Chinese quince.
Usesp-Vinylguaiacol is an aromatic substance and one of the compounds responsible for the natural aroma of buckwheat. It is also one of the major pyrolytic products of (E)-N-[(4-hydroxy-3-methoxy)-phenethyl]-3-[(3-methoxy-4-O-β-D-glucopyranosyloxy) phenyl] acrylamide; a new gycloside in tobacco.
General Description2-Methoxy-4-vinylphenol is one of the key volatile aroma compounds of buckwheat and okra.
Preparation methods
PreparationFrom vanillin by reacting with acetic anhydride and sodium acetate yielding 3-methoxy-4-hydroxycinnamic acid on sub sequent hydrolysis; the latter, heated with quinoline in the presence of hydroquinone, is decarboxylated to 4-vinylguaiacol.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
1 records
Compound notes
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