31853-85-7

Basic information

• Product Name: Phenol,4-ethenyl-2-methoxy-, homopolymer
• Synonyms: Phenol,2-methoxy-4-vinyl-, polymers (8CI); 3-Methoxy-4-hydroxystyrene polymer; 4-Hydroxy-3-methoxystyrene polymer; 4-Vinyl-2-methoxyphenol homopolymer; Poly(3-methoxy-4-hydroxystyrene); Poly(4-hydroxy-3-methoxystyrene); Poly(4-vinylguaiacol); Poly(vinylguaiacol)
• CAS NO: 31853-85-7
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.1745
• Mol File: 31853-85-7.mol
• Article Data: 68

Chemical Properties

• Boiling Point: 245°Cat760mmHg
• Flash Point: 111.3°C
• Density: 1.089g/cm³
• CAS DataBase Reference: Phenol,4-ethenyl-2-methoxy-, homopolymer(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol,4-ethenyl-2-methoxy-, homopolymer(31853-85-7)
• EPA Substance Registry System: Phenol,4-ethenyl-2-methoxy-, homopolymer(31853-85-7)

Safety Data

• Hazardous Substances Data: 31853-85-7(Hazardous Substances Data)

Usage

General Description

Phenol, 4-ethenyl-2-methoxy, homopolymer, also known as polyvinyl guaiacol, is a chemical compound that is a polymer of 4-ethenyl-2-methoxyphenol, a derivative of phenol. It is a white to slightly yellow solid and is insoluble in water. Phenol,4-ethenyl-2-methoxy-, homopolymer is used as an antioxidant in various polymer products, as well as a stabilizer and a crosslinking agent in rubber products. It also has applications in the pharmaceutical industry, for the formulation of oral and topical drug delivery systems, and in the production of coatings and adhesives. Additionally, polyvinyl guaiacol is used as a resin modifier for dental and biomedical materials, and as an additive in the manufacture of food and beverages to prevent oxidation and extend shelf life.

Upstream product

• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 93006-77-0 4,4-(ethane-1,1-diyl)bis(2-methoxyphenol) 
• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 121-33-5 vanillin 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 46316-15-8 4-acetoxy-3-methoxyvinylbenzene 
• 2480-86-6 Apocynol 
• 141-82-2 malonic acid 
• 881-68-5 vanillin acetate 
• 96943-24-7 acetic acid 4-(1-hydroxy-ethyl)-2-methoxy-phenyl ester 
• 1252786-11-0 C₄H₁₁N*C₁₀H₁₀O₄ 
• 1252786-15-4 C₅H₁₁N*C₁₀H₁₀O₄ 

Downstream Products

• 60623-13-4 4-benzoyloxy-3-methoxy-styrene 
• 10083-24-6 trans-piceatannol 
• 33626-09-4 (E)-3,3',5,5'-tetrahydroxystilbene 
• 1335096-75-7 (2E)-3-{4-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]phenyl}prop-2-enoic acid 
• 1342818-14-7 3'-bromo-4,6'-dimethoxy-2-formyl-4'-{2-[3-(4-(bromomethyl)phenoxy)-4-methoxyphenyl]ethyl}biphenyl 
• 1344912-75-9 (S)-4-(1-hydroxyethyl)-2-methoxyphenol 

Relevant articles and documents

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Synthesis of styrenes through the biocatalytic decarboxylation of trans-cinnamic acids by plant cell cultures

A novel method for producing styrenes from trans-cinnamic acids was developed. When trans-cinnamic acid was incubated with plant cell cultures at room temperature, styrene was obtained. 4-Hydroxy-3-methoxystyrene (2a), 3-nitrostyrene (2f) and furan (2g) were synthesized quantitatively.

The bio-based phthalocyanine resins with high Tg and high char yield derived from vanillin

The conversion of bio-based vanillin into the heat-resistant polymers is investigated. Firstly, converting the aldehyde group of vanillin into a vinyl group obtained 2-methoxy-4-vinylphenol (S1), which was then treated with nitro-phthalonitrile to give 4-(2-methoxy-4-vinylphenoxy)phthalonitrile (S2). Secondly, thermal polymerization between S1 and S2 in a different molar ratio gave a series of vanillin–based phthalocyanine (V-PN) resins that display high char yield and high Tg. The best result was obtained when the molar ratio between S1 and S2 was 1–50 and the obtained V-PN resin displayed a char yield of up to 76%, a Tg over 400 °C. These data are much better than those of the widely used petroleum-based phthalocyanine resins, suggesting that these bio-based functional monomers derived from vanillin are suitable as the precursors for the fabrication of the ablation-resistant materials in the application of the aerospace industry.

Host attractants for red weevil, Rhynchophorus ferrugineus: Identification, electrophysiological activity, and laboratory bioassay

A steam distillate from the freshly cut young bark of coconut palm Cocos nucifera was analyzed by gas chromatography, combined gas chromatography-electroantennographic detection (GC-EAD) and GC-MS to detect host attractants for the curculionid weevil Rhynchophorus ferrugineus, one of the major coconut pests in Sri Lanka. A twin FID peak consisting of a minor and a major component was shown to possess electrophysiological (EAG) activity. The minor peak was identified as γ-nonanoic lactone 2, while the major peak was identified as 4-hydroxy-3-methoxystyrene 2. In an EAG assay the synthetic racemic nonanoic lactone 1 did not elicit a considerable response in the antenna of R. ferrugineus, whereas the laboratory synthesized 2 showed activity. In a laboratory bioassay using a Y-type olfactometer, synthetic 1 and 2 elicited moderate attractant properties to R. ferrugineus, whereas a 1:1 mixture of the compounds showed increased attraction over that of the individual compounds.

Synthesis of Lipophilic Antioxidants by a Lipase-B-Catalyzed Addition of Peracids to the Double Bond of 4-Vinyl-2-methoxyphenol

4-Vinyl guaiacol (2) was lipophilized through the electrophilic addition of peracids to its vinylic double bond. Those peracids were formed in situ, by the Candida antarctica lipase-B-assisted perhydrolysis of carboxylic acids ranging from C2 to C18, in hydrogen peroxide solution. The addition of peracids with 4-8 carbons in their alkyl chains led to the formation of two regioisomers, with the prevalence of hydroxyesters bearing a primary free hydroxyl (4c-4e). This prevalence became more pronounced when peracids with longer alkyl chains (C10-C18) were used. In this case, only isomers 4f-4h were formed. The antioxidant activity of the resulting hydroxyesters was assessed by means of the conjugated autoxidizable triene (CAT) assay, and it was found out that the 4-vinyl guaiacol antioxidant activity was significantly increased by grafting alkyl chains with 2-8 carbons.

Rapid biosynthesis of phenolic glycosides and their derivatives from biomass-derived hydroxycinnamates

Biomass-derived hydroxycinnamates (mainly includingp-coumaric acid and ferulic acid), which are natural sources of aromatic compounds, are highly underutilized resources. There is a need to upgrade them to make them economically feasible. Value-added phenolic glycosides and their derivatives, both belonging to a class of plant aromatic natural products, are widely used in the nutraceutical, pharmaceutical, and cosmetic industries. However, their complex aromatic structures make their efficient biosynthesis a challenging process. To overcome this issue, we created three novel synthetic cascades for the biosynthesis of phenolic glycosides (gastrodin, arbutin, and salidroside) and their derivatives (hydroquinone, tyrosol, hydroxytyrosol, and homovanillyl alcohol) fromp-coumaric acid and ferulic acid. Moreover, because the biomass-derived hydroxycinnamates directly provided aromatic units, the cascades enabled efficient biosynthesis. We achieved substantially high production rates (up to or above 100-fold enhancement) relative to the glucose-based biosynthesis. Given the ubiquity of the aromatic structure in natural products, the use of biomass-derived aromatics should facilitate the rapid biosynthesis of numerous aromatic natural products.

Discovery, Biocatalytic Exploration and Structural Analysis of a 4-Ethylphenol Oxidase from Gulosibacter chungangensis

The vanillyl-alcohol oxidase (VAO) family is a rich source of biocatalysts for the oxidative bioconversion of phenolic compounds. Through genome mining and sequence comparisons, we found that several family members lack a generally conserved catalytic aspartate. This finding led us to study a VAO-homolog featuring a glutamate residue in place of the common aspartate. This 4-ethylphenol oxidase from Gulosibacter chungangensis (Gc4EO) shares 42 % sequence identity with VAO from Penicillium simplicissimum, contains the same 8α-N3-histidyl-bound FAD and uses oxygen as electron acceptor. However, Gc4EO features a distinct substrate scope and product specificity as it is primarily effective in the dehydrogenation of para-substituted phenols with little generation of hydroxylated products. The three-dimensional structure shows that the characteristic glutamate side chain creates a closely packed environment that may limit water accessibility and thereby protect from hydroxylation. With its high thermal stability, well defined structural properties and high expression yields, Gc4EO may become a catalyst of choice for the specific dehydrogenation of phenolic compounds bearing small substituents.