3897-89-0

Usage

Uses

Used in Pharmaceutical Applications:
3,4-Dihydroxybenzyl alcohol is used as a therapeutic agent for its antioxidant, anti-inflammatory, anticancer, antidiabetic, and neuroprotective properties. It is particularly beneficial in the treatment and management of various diseases and conditions that can be alleviated by these pharmacological activities.
Used in Industrial Applications:
3,4-Dihydroxybenzyl alcohol is used as a key component in the production of polymers, dyes, and fragrances. Its chemical reactivity and the presence of functional groups in its molecular structure make it a valuable raw material in these industries.
Used in Traditional Medicine:
3,4-Dihydroxybenzyl alcohol is used as a natural remedy in traditional medicine practices, where its broad range of pharmacological activities is harnessed to promote health and well-being. It is often incorporated into herbal formulations and supplements for its potential therapeutic benefits.

Upstream product

• 1699-58-7 3,4-bis(benzyloxy)benzyl alcohol 
• 452-86-8 4-methyl-1,2-dihydroxybenzene 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 2150-43-8 3,4-dihydroxybenzoic acid methyl ester 
• 113118-24-4 acetic acid 2-acetoxy-4-hydroxymethyl-phenyl ester 
• 120-57-0 piperonal 
• 331-39-5 caffeic acid 
• 4383-06-6 3-hydroxy-4-methoxybenzyl alcohol 
• 775-01-9 3,4-dihydroxymandelic acid 
• 102-32-9 3,4-dihydroxyphenylacetate 
• 620-92-8 bis-(4-hydroxyphenyl)methane 
• 139-85-5 3,4-dihydroxybenzaldehyde 

Downstream Products

• 21086-81-7 2,5-Bis(phenylamino)-4-phenylimino-2,5-cyclohexadienone 
• 7461-66-7 4,5-dianilinobenzo-1,2-quinone 
• 4009-81-8 4-[bis-(2-hydroxy-ethyl)-amino]-[1,2]benzoquinone 
• 191164-60-0 (3S,3aS,6S,6aR)-3-(3,4-Dihydroxy-benzyl)-3,3a,6-trihydroxy-tetrahydro-furo[3,2-b]furan-2-one 
• 17345-61-8 3,4-dihydroxybenzonitrile 
• 802830-84-8 4-[Bis-(2-hydroxy-ethyl)-amino]-benzene-1,2-diol 
• 90944-19-7 4-[Bis-(2-chloro-ethyl)-amino]-benzene-1,2-diol 
• 68292-30-8 C₉H₁₀O₄ 
• 1633353-53-3 4-(((tert-butyldimethylsilyl)oxy)methyl)benzene-1,2-diol 
• 3943-89-3 Ethyl protocatechuate 

Relevant academic research and scientific papers

Preparation of artificial urushi via an environmentally benign process

"Artificial urushi" has been developed by laccase-catalyzed curing of new urushiol analogues. The analogues were designed and conveniently synthesized by regioselective acylation of phenol derivatives having a primary alcohol with unsaturated fatty acids using lipase as catalyst. The curing of the catechol derivative having a linolenoyl group proceeded in the presence of acetone powder from Chinese urushi, yielding the crosslinked film ("artificial urushi") with high hardness and gloss surface, which are comparable with those of natural urushi coating. The analogues obtained from vanillyl alcohol were also cured. FT-IR monitoring of the curing showed that the crosslinking mechanism was similar to that of the natural urushi. The curing of the urushiol analogues in the presence of starch-urea phosphate took place to give the artificial urushi consisting exclusively of synthetic compounds.

Thiols Act as Methyl Traps in the Biocatalytic Demethylation of Guaiacol Derivatives

Demethylating methyl phenyl ethers is challenging, especially when the products are catechol derivatives prone to follow-up reactions. For biocatalytic demethylation, monooxygenases have previously been described requiring molecular oxygen which may cause oxidative side reactions. Here we show that such compounds can be demethylated anaerobically by using cobalamin-dependent methyltransferases exploiting thiols like ethyl 3-mercaptopropionate as a methyl trap. Using just two equivalents of this reagent, a broad spectrum of substituted guaiacol derivatives were demethylated, with conversions mostly above 90 %. This strategy was used to prepare the highly valuable antioxidant hydroxytyrosol on a one-gram scale in 97 % isolated yield.

Biocatalytic Methyl Ether Cleavage: Characterization of the Corrinoid-Dependent Methyl Transfer System from Desulfitobacterium hafniense

The ether functionality represents a very common motif in organic chemistry and especially the methyl ether is commonly found in natural products. Its formation and cleavage can be achieved via countless chemical procedures. Nevertheless, since in particular the cleavage often involves harsh reaction conditions, milder alternatives are highly demanded. Very recently, we have reported on a biocatalytic shuttle catalysis concept for reversible cleavage and formation of phenolic O-methyl ethers employing a corrinoid-dependent methyl transferase system from the anaerobic organism Desulfitobacterium hafniense. Here we report the technical study of this system, focusing on the demethylation of guaiacol as model reaction. The optimal buffer-, pH-, temperature- and cofactor-preferences were determined as well as the influence of organic co-solvents. Beside methyl cobalamin also hydroxocobalamin turned out to be a suitable cofactor species, although the latter required activation. Various O-methyl phenyl ethers were successfully demethylated with conversions up to 82% at 10 mM substrate concentration. (Figure presented.).

Phenolic constituents from the twigs of Betula schmidtii collected in Goesan, Korea

Six undescribed phenolic derivatives along with thirty two known compounds were isolated from the twigs of Betula schmidtii. The chemical structures were characterized through extensive spectroscopic analysis and chemical methods. All known compounds were first isolated in this plant. The anti-inflammatory effect of the isolates was tested by measuring nitric oxide production in lipopolysaccharide-activated BV-2 cells. Isotachioside, 4-allyl-2-hydrophenyl 1-O-β-D-apiosyl-(1 → 6)-β-D-glucopyranoside, genistein 5-O-β-D-glucoside, and prunetinoside showed a slight potency to lower the NO production against LPS-activated microglia with IC50 values of 23.9, 25.3, 28.8, and 34.0 μM, respectively.

Temperature-Directed Biocatalysis for the Sustainable Production of Aromatic Aldehydes or Alcohols

The biosynthesis of aromatic aldehydes and alcohols from renewable resources is currently receiving considerable attention because of an increase in demand, finite fossil resources, and growing environmental concerns. Here, a temperature-directed whole-cell catalyst was developed by using two novel enzymes from a thermophilic actinomycete. Ferulic acid, a model lignin derivative, was efficiently converted into vanillyl alcohol at a reaction temperature at 30 °C. However, when the temperature was increased to 50 °C, ferulic acid was mainly converted into vanillin with a productivity of 1.1 g L?1 h?1. This is due to the fact that the redundant endogenous alcohol dehydrogenases (ADHs) are not active at this temperature while the functional enzymes from the thermophilic strain remain active. As the biocatalyst could convert many other renewable cinnamic acid derivatives into their corresponding aromatic aldehydes/alcohols, this novel strategy may be extended to generate a vast array of valuable aldehydes or alcohols.

CSJ acting as a versatile highly efficient greener resource for organic transformations

Simple, new, greener and efficient alternatives to the existing protocols have been developed for the reduction of aromatic aldehydes to their corresponding alcohols, decarboxylation of substituted benzoic acids (C6-C1) and substituted cinnamic acids (C6-C3) with a hydroxyl group at the para position with respect to the acid group to corresponding phenolic compounds and vinyl phenols respectively by using a natural feedstock, cucumber juice (CSJ), which acts as a greener solvent system, performing a substrate-selective reaction. Additionally, the hydrolysis of the acetyl as well as the benzoyl group of aromatic compounds has been carried out to afford excellent yield by CSJ.

The metabolic fate of ortho-quinones derived from catecholamine metabolites

ortho-Quinones are produced in vivo through the oxidation of catecholic substrates by enzymes such as tyrosinase or by transition metalions. Neuromelanin, a dark pigment present in the substantia nigra and locus coeruleus of the brain, is produced from dopamine (DA) and norepinephrine (NE) via an interaction with cysteine, but it also incorporates their alcoholic and acidic metabolites. In this study we examined the metabolic fate of ortho-quinones derived from the catecholamine metabolites, 3,4-dihydroxyphenylethanol (DOPE), 3,4-dihydroxyphenylethylene glycol (DOPEG), 3,4-dihydroxyphenylacetic acid (DOPAC) and 3,4-dihydroxyphenylmandelic acid (DOMA). The oxidation of catecholic substrates by mushroom tyrosinase was followed by UV-visible spectrophotometry. HPLC analysis after reduction with NaBH4 or ascorbic acid enabled measurement of the half-lives of ortho-quinones and the identification of their reaction products. Spectrophotometric examination showed that the ortho-quinones initially formed underwent extensive degradation at pH 6.8. HPLC analysis showed that DOPE-quinone and DOPEG-quinone degraded with half-lives of 15 and 30 min at pH 6.8, respectively, and >100 min at pH 5.3. The major product from DOPE-quinone was DOPEG which was produced through the addition of a water molecule to the quinone methide intermediate. DOPEG-quinone yielded a ketone, 2-oxo-DOPE, through the quinone methide intermediate. DOPAC-quinone and DOMA-quinone degraded immediately with decarboxylation of the ortho-quinone intermediates to form 3,4-dihydroxybenzylalcohol (DHBAlc) and 3,4-dihydroxybenzaldehyde (DHBAld), respectively. DHBAlc-quinone was converted to DHBAld with a half-life of 9 min, while DHBAld-quinone degraded rapidly with a half-life of 3 min. This study confirmed the fact that ortho-quinones from DOPE, DOPEG, DOPAC and DOMA are converted to quinone methide tautomers as common intermediates, through proton rearrangement or decarboxylation. The unstable quinone methides afford stable alcoholic or carbonyl products.

Photochemistry of bisphenol F in aqueous solutions: A mechanistic study

In the present work aqueous photochemistry of bisphenol F has been studied by means of stationary (282 nm) and laser flash photolysis (266 nm). Photoionization with formation of hydrated electron - phenoxyl radical pair was observed to be the main primary photochemical process (φmono = 2 × 10-2). Phenoxyl radical decays in recombination and reaction with superoxide anion radical formed during scavenging of hydrated electron by dissolved oxygen. The quantum yield of BPF photodegradation was evaluated to be 2 × 10-3 upon 282 nm exposure. The main primary product of BPF photolysis determined by LC-MS is hydroxylated BPF.

Design, synthesis and biological evaluation of small molecular polyphenols as entry inhibitors against H5N1

To find novel compounds against H5N1, three series of known or novel small molecular polyphenols were synthesized and tested in vitro for anti-H5N1 activity. In addition, the preliminary structure-antiviral activity relationships were elaborated. The results showed that some small molecular polyphenols had better anti-H5N1 activity, and could serve as novel virus entry inhibitors against H 5N1, likely targeting to HA2 protein. Noticeably, compound 4a showed the strongest activity against H5N1 among these compounds, and the molecular modeling analysis also suggested that this compound might target to HA2 protein. Therefore, compound 4a is well qualified to serve as a lead compound or scaffold for the further development of H 5N1 entry inhibitor.

Electrophilicity and nucleophilicity of commonly used aldehydes

The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO4 oxidation and NaBH4 reduction of aldehydes. A transition state analysis of the KMNO4 promoted aldehyde oxidation reaction has been performed, which shows a very good correlation with experimental results. The validity of the experimental method has been tested using the experimental activation parameters of the two reactions. The utility of the present approach is further demonstrated by the theoretical versus experimental relationship, which provides easy access to E and N values for various aldehydes and offers an at-a-glance assessment of the chemical reactivity of aldehydes in various reactions. the Partner Organisations 2014.