7786-61-0

Basic information

• Product Name: 4-Hydroxy-3-methoxystyrene
• Synonyms: 2-methoxy-4-vinyl-pheno;2-Methoxy-4-vinylphenol (4-vinylguaiacol);2-methoxy-4-vinylphenol (vinylguaiacol);2-metoxy-4-vinyl-phenol;4-ethenyl-2-methoxy-pheno;4-Ethenyl-2-methoxyphenol;4-ethenyl-2-methoxy-Phenol;4-Vinyl-2-methoxyphenol (4-vinylguaiacol)
• CAS NO: 7786-61-0
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• EINECS: 232-101-2
• Product Categories: Pharmaceutical Raw Materials;Aromatic Phenols;phenol Flavor;Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 7786-61-0.mol
• Article Data: 68

Chemical Properties

• Melting Point: 25-29°C
• Boiling Point: 224 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.11 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0188mmHg at 25°C
• Refractive Index: n20/D 1.582(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slig
• PKA: 10.00±0.31(Predicted)
• Water Solubility: Miscible with water.
• Stability: Light Sensitive
• BRN: 2044521
• CAS DataBase Reference: 4-Hydroxy-3-methoxystyrene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-3-methoxystyrene(7786-61-0)
• EPA Substance Registry System: 4-Hydroxy-3-methoxystyrene(7786-61-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: SL8205000
• TSCA: Yes
• Hazardous Substances Data: 7786-61-0(Hazardous Substances Data)

Usage

Chemical Properties

2-Methoxy-4-vinylphenol has a powerful, spicy, apple, rum, roasted peanut aroma.

Occurrence

Reported 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.

Uses

p-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.

Definition

ChEBI: A member of the class of phenols that is guaiacol in which the hydrogen para- to the hydroxy group is replaced by a vinyl group.

Preparation

From 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.

Aroma threshold values

Detection; 0.75 to 3 ppb

General Description

2-Methoxy-4-vinylphenol is one of the key volatile aroma compounds of buckwheat and okra.

InChI:InChI=1/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3

Upstream product

• 93006-77-0 4,4-(ethane-1,1-diyl)bis(2-methoxyphenol) 
• 498-02-2 1-(3-methoxy-4-hydroxyphenyl)ethanone 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 122-48-5 4-(4-hydroxy-3-methoxyphenyl)-2-butanone 
• 2785-89-9 4-Ethylguaiacol 
• 1530-32-1 ethyltriphenylphosphonium bromide 
• 121-33-5 vanillin 
• 20649-42-7 coniferaldehyde 
• 97-53-0 4-allylguaiacol 
• 74-85-1 ethene 
• 97-54-1 2-methoxy-4-propenylphenol 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 9005-53-2 lignin 

Downstream Products

• 60623-13-4 4-benzoyloxy-3-methoxy-styrene 
• 121-33-5 vanillin 
• 2785-89-9 4-Ethylguaiacol 

Relevant articles and documents

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.

Efficient synthesis of styrene derivatives through ethenolysis of renewable propenylbenzenes

Functionalized styrenes were obtained by the ethenolysis of renewable 1-propenylbenzenes in a very efficient synthetic pathway. Some of the products are valuable food & flavor ingredients (4-vinylguaiacol) or locust pheromone (4-vinylanisole). The catalysts employed were ruthenium-alkylidene complexes bearing a N-heterocyclic carbene as a ligand, which bulkiness proved to be important for the catalysis output. The judicious choice the reaction conditions was critical to enable near quantitative yields under mild conditions in short reaction times. More strikingly, the catalyst load could be reduced to 0.01 mol%, keeping good conversion and selectivity.

New hybrids based on curcumin and resveratrol: Synthesis, cytotoxicity and antiproliferative activity against colorectal cancer cells

We synthesized twelve hybrids based on curcumin and resveratrol, and their structures were elucidated by spectroscopic analysis. The chemopreventive potential of these compounds was evaluated against SW480 human colon adenocarcinoma cells, its metastatic derivative SW620, along with the non-malignant CHO-K1 cell line. Among the tested compounds, hybrids 3e and 3i (for SW480) and 3a, 3e and 3k (for SW620) displayed the best cytotoxic activity with IC50 values ranging from 11.52 ± 2.78 to 29.33 ± 4.73 μM for both cell lines, with selectivity indices (SI) higher than 1, after 48 h of treatment. Selectivity indices were even higher than those reported for the reference drug, 5-fluorouracil (SI = 0.96), the starting compound resveratrol (SI = 0.45) and the equimolar mixture of curcumin plus resveratrol (SI = 0.77). The previous hybrids showed good antiproliferative activity.