Guaiacol

CAS# 90-05-1

Guaiacol

2D Structure

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Guaiacol

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Chemical Properties of Guaiacol

Cas No. 90-05-1 SDF Download SDF
PubChem ID 460 Appearance White crystalline powder
Formula C7H8O2 M.Wt 124.13
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 100 mg/mL (805.54 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 2-methoxyphenol
SMILES COC1=CC=CC=C1O
Standard InChIKey LHGVFZTZFXWLCP-UHFFFAOYSA-N
Standard InChI InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Guaiacol Dilution Calculator

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Preparing Stock Solutions of Guaiacol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 8.0561 mL 40.2804 mL 80.5607 mL 161.1214 mL 201.4018 mL
5 mM 1.6112 mL 8.0561 mL 16.1121 mL 32.2243 mL 40.2804 mL
10 mM 0.8056 mL 4.028 mL 8.0561 mL 16.1121 mL 20.1402 mL
50 mM 0.1611 mL 0.8056 mL 1.6112 mL 3.2224 mL 4.028 mL
100 mM 0.0806 mL 0.4028 mL 0.8056 mL 1.6112 mL 2.014 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Guaiacol

Characterization of novel heat-responsive transcription factor (TaHSFA6e) gene involved in regulation of heat shock proteins (HSPs) - A key member of heat stress-tolerance network of wheat.[Pubmed:29746879]

J Biotechnol. 2018 Aug 10;279:1-12.

Heat stress has an adverse effect on the quality and quantity of agriculturally important crops, especially wheat. The tolerance mechanism has not been explored much in wheat and very few genes/ TFs responsive to heat stress is available on public domain. Here, we identified, cloned and characterized a putative TaHSFA6e TF gene of 1.3 kb from wheat cv. HD2985. We observed an ORF of 368 aa with Hsf DNA binding signature domain in the amino acid sequence. Single copy number of TaHSFA6e was observed integrated in the genome of wheat. Expression analysis of TaHSFA6e under differential HS showed maximum transcripts in wheat cv. Halna (thermotolerant) in response to 38 degrees C for 2h during pollination and grain-filling stages, as compared to PBW343, HD2329 and HD2985. Putative target genes of TaHSFA6e (HSP17, HSP70 and HSP90) showed upregulation in response to differential HS (30 & 38 degrees C, 2h) during pollination and grain-filling stages. Small HSP17 was observed most triggered in Halna under HS. We observed increase in the catalase, Guaiacol peroxidase, total antioxidant capacity (TAC), and decrease in the lipid peroxidation in thermotolerant cvs. (Halna, HD2985), as compared to thermosusceptible (PBW343, HD2329) under differential HS. Multiple stresses (heat - 38 degrees C, 2h, and drought - 100mL of 20% polyethylene Glycol 6000) during seedling stage of wheat showed positive correlation between the expression of TaHSFA6e, putative targets (HSP70, HSP90, HSP17) and TAC. Halna (thermotolerant) performed better, as compared to other contrasting cvs. TaHSFA6e TF can be used as promising candidate gene for manipulating the heat stress-tolerance network.

[Enzymatic characteristics of peroxidase from Chrysanthemum morifolium cv. Bo-ju].[Pubmed:29751705]

Zhongguo Zhong Yao Za Zhi. 2018 Apr;43(8):1596-1601.

The enzymatic browning is one of the main reasons for affecting the quality of medicinal flowers. In the process of chrysanthemum harvesting and processing, improper treatment will lead to the browning and severely impact the appearance and quality of chrysanthemum. Peroxidase enzyme is one of the oxidoreductases that cause enzymatic browning of fresh chrysanthemum. The enzymatic characteristics of peroxidase (POD) in chrysanthemum were studied in this paper. In this experiment, the effects of different reaction substrates and their concentrations, PH value of buffer and reaction temperatures on the activity of POD enzyme were investigated. The results showed that the optimal substrate of POD was Guaiacol, and the optimal concentration of POD was 50 mmol.L(-)(1). The optimal pH value and reaction temperature were 4.4 and 30-35 degrees C, respectively. Michaelis-Menten equation was obtained to express the kinetics of enzyme-catalyzed reaction of POD, Km=0.193 mol.L(-)(1), Vmax=0.329 D.min(-)(1). In addition, the results of POD enzyme thermal stability test showed that the POD enzyme activity was inhibited when being treated at 80 degrees C for 4 min or at 100 degrees C for 2 min. The above results were of practical significance to reveal the enzymatic browning mechanism, control the enzymatic browning and improve the quality of chrysanthemum, and can also provide the basis for the harvesting and processing of medicinal materials containing polyphenols.

Catalytic cracking of model compounds of bio-oil over HZSM-5 and the catalyst deactivation.[Pubmed:29727985]

Sci Total Environ. 2018 Aug 1;631-632:1611-1622.

The catalytic cracking upgrading reactions over HZSM-5 of different model compounds of bio-oil have been studied with a self-designed fluid catalytic cracking (FCC) equipment. Typical bio-oil model compounds, such as acetic acid, Guaiacol, n-heptane, acetol and ethyl acetate, were chosen to study the products distribution, reaction pathway and deactivation of catalysts. The results showed: C6-C8 aromatic hydrocarbons, C2-C4 olefins, C1-C5 alkanes, CO and CO2 were the main products, and the selectivity of olefins was: ethylene>propylene>butylene. Catalyst characterization methods, such as FI-IR, TG-TPO and Raman, were used to study the deactivation mechanism of catalysts. According to the catalyst characterization results, a catalyst deactivation mechanism was proposed as follows: Firstly, the precursor which consisted of a large number of long chain saturated aliphatic hydrocarbons and a small amount CC of aromatics formed on the catalyst surface. Then the active sites of catalysts had been covered, the coke type changed from thermal coke to catalytic coke and gradually blocked the channels of the molecular sieve, which accelerated the deactivation of catalyst.

Biodegradation of Lignin Monomers Vanillic, p-Coumaric, and Syringic Acid by the Bacterial Strain, Sphingobacterium sp. HY-H.[Pubmed:29750329]

Curr Microbiol. 2018 Sep;75(9):1156-1164.

Many bacterial strains have been demonstrated to biodegrade lignin for contaminant removal or resource regeneration. The goal of this study was to investigate the biodegradation amount and associated pathways of three lignin monomers, vanillic, p-coumaric, and syringic acid by strain Sphingobacterium sp. HY-H. Vanillic, p-coumaric, and syringic acid degradation with strain HY-H was estimated as 88.71, 76.67, and 72.78%, respectively, after 96 h. Correspondingly, the same three monomers were associated with a COD removal efficiency of 87.30, 55.17, and 67.23%, and a TOC removal efficiency of 82.14, 61.03, and 43.86%. The results of GC-MS, HPLC, FTIR, and enzyme activities show that Guaiacol and o-dihydroxybenzene are key intermediate metabolites of the vanillic acid and syringic acid degradation. p-Hydroxybenzoic acid is an important intermediate metabolite for p-coumaric and syringic acid degradation. LiP and MnP play an important role in the degradation of lignin monomers and their intermediate metabolites. One possible pathway is that strain HY-H degrades lignin monomers into Guaiacol (through decarboxylic and demethoxy reaction) or p-hydroxybenzoic acid (through side-chain oxidation); then Guaiacol demethylates to o-dihydroxybenzene. The p-hydroxybenzoic acid and o-dihydroxybenzene are futher through ring cleavage reaction to form small molecule acids (butyric, valproic, oxalic acid, and propionic acid) and alcohols (ethanol and ethanediol), then these acids and alcohols are finally decomposed into CO2 and H2O through the tricarboxylic acid cycle. If properly optimized and controlled, the strain HY-H may play a role in breaking down lignin-related compounds for biofuel and chemical production.

Increase in Artemisia annua Plant Biomass Artemisinin Content and Guaiacol Peroxidase Activity Using the Arbuscular Mycorrhizal Fungus Rhizophagus irregularis.[Pubmed:29706981]

Front Plant Sci. 2018 Apr 13;9:478.

The main objective of this study was to investigate Artemisia annua plant property variations in terms of plant biomass, glandular trichome numbers, artemisinin production and Guaiacol peroxidase (GPOX) activity when plants are in mutualism with AMF. According to the results, A. annua mutualism with AMF significantly increased the most important and pharmaceutically relevant factors of fresh and dry plant biomass. This increase, especially in the biomass of plant herba (leaves), was 30% higher during the vegetation period and remained high (29% higher than for control) when plants were harvested at the end of the vegetation period. Similar differences in dry biomass were also detected. Glandular trichomas numbers increased by 40%, and the artemisinin content by 17% under AMF colonization. No effects due to AMF on chlorophyll variations were detected, while GPOX enzyme concentrations increased significantly under AMF colonization. Altogether the Artemisia plant properties with high pharmaceutically importance (fresh and dry biomass of leaves and artemisinin, number of trichomes and the artemisinin content) were significantly improved by AMF, the application in Artemisia cultivation can be an effective and cheap method. The high GPOX activity under AMF colonization indicate an enhanced oxidative stress alleviation, therefore a higher resistance to water deficiency, mechanisms important under climate conditions with low water supply where Artemisia is usually cultivated.

Toxicity assessment of cobalt ferrite nanoparticles on wheat plants.[Pubmed:29737961]

J Toxicol Environ Health A. 2018;81(14):604-619.

Cobalt ferrite nanoparticles (NPs) have received increasing attention due to their widespread therapeutic and agricultural applicability. In the environmental field, dry powder- and ferrofluid-suspended cobalt ferrite NPs were found to be useful for removing heavy metals and metalloids from water, while diluted suspensions of cobalt ferrite NP have been promisingly applied in medicine. However, the potential toxicological implications of widespread exposure are still unknown. Since cobalt ferrite NPs are considered residual wastes of environmental or medical applications, plants may serve as a point-of-entry for engineered nanomaterials as a result of consumption of these plants. Thus, the aim of this study was to assess the effects of dry powder and fresh cobalt ferrite NP on wheat plants. Seven-day assays were conducted, using quartz sand as the plant growth substrate. The toxicity end points measured were seed germination, root and shoot lengths, total cobalt (Co) and iron (Fe) accumulation, photosynthetic pigment production, protein (PRT) production, and activities of catalase (CAT), ascorbate peroxidase (APX), and Guaiacol peroxidase (GPX). Increasing total Co and Fe in plant tissues indicated that wheat plants were exposed to cobalt ferrite NP. Seed germination and shoot length were not sufficiently sensitive toxicity end points. The effective concentration (EC50) that diminished root length of plants by 50% was 1963 mg/kg for fresh ferrite NPs and 5023 mg/kg for powder ferrite NP. Hence, fresh ferrite NPs were more toxic than powder NP. Plant stress was indicated by a significant decrease in photosynthetic pigments. CAT, APX, and GPX antioxidant enzymatic activity suggested the generation of reactive oxygen species and oxidative damage induced by cobalt ferrite NP. More studies are thus necessary to determine whether the benefits of using these NPs outweigh the risks.

Activities of Versatile Peroxidase in Cultures of Clonostachys rosea f. catenulata and Clonostachys rosea f. rosea during Biotransformation of Alkali Lignin.[Pubmed:29724265]

J AOAC Int. 2018 Sep 1;101(5):1415-1421.

The aim of this study was the evaluation of activities of versatile peroxidase (VP) in cultures of Clonostachys sp. (Gliocladium sp.) strains during biotransformation of 0.2% alkali lignin (AL). The principal component analysis (PCA) method was applied to determine the main factors and correlation between biotransformation of 0.2% AL, activity of VPs, pH value, and Clonostachys sp. strains. The biotransformation of 0.2% AL in cultures of microscopic fungi included decolorization (medium lightening) and colorization (darkening of the medium). The versatile peroxidase synthesized by the microscopic fungi tested showed activity for oxidation of Mn(II) and Guaiacol, but the activity for oxidation of Guaiacol in the presence of Mn(II) was significantly higher. The PCA analysis indicated a strong correlation between biotransformation of 0.2% AL and pH and between oxidation of Mn(II), Guaiacol without and in the presence of Mn(II) ions, strains, and pH.

Selenium and silicon reduce cadmium uptake and mitigate cadmium toxicity in Pfaffia glomerata (Spreng.) Pedersen plants by activation antioxidant enzyme system.[Pubmed:29700750]

Environ Sci Pollut Res Int. 2018 Jul;25(19):18548-18558.

Cadmium (Cd) is toxic to plants and animals, making it necessary to develop strategies that seek to reduce its introduction into food chains. Thus, the aim of this study was to investigate whether silicon (Si) and selenium (Se) reduce Cd concentrations in Pfaffia glomerata medicinal plant and attenuate the oxidative stress promoted by this metal. These plants were cultivated in hydroponics under the following treatments: control (nutrient solution), 2.5 muM Se, 2.5 mM Si, 50 muM Cd, 50 muM Cd + 2.5 muM Se, 50 muM Cd + 2.5 mM Si. After 14 days of exposure to treatments, leaves and roots were collected for the determination of dry weight of shoot and roots, Cd concentrations, chlorophyll and carotenoids content, and biochemical parameters (lipid peroxidation and Guaiacol peroxidase and superoxide dismutase activities). The data were submitted to analysis of variance and means were compared with Scott-Knott test at 5% error probability. Roots of P. glomerata plants showed a significant reduction on dry weight accumulation when exposed to Cd. However, both Se and Si promoted a significant reduction of deleterious effects of Cd. The Cd concentrations in the tissues were reduced in the presence of Se or Si. Plants treated with Cd together with Se or Si presented higher pigment content than those with only Cd, thus showing a reduction in the negative effects caused by this element. In the treatments in which Se and Si were added in the growth medium together with Cd, an activation of superoxide dismutase and Guaiacol peroxidase enzymes was observed in the roots and shoot, which may have contributed to lower lipid peroxidation. Thus, Se and Si reduce Cd concentrations and have potential to ameliorate Cd toxicity in P. glomerata plants, which can be used to increase productivity and quality of medicinal plants.

Description

Guaiacol, a phenolic compound isolated from Guaiac resin, inhibits LPS-stimulated COX-2 expression and NF-κB activation. Anti-inflammatory activity.

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