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1,2-Benzenediol

CAS# 120-80-9

1,2-Benzenediol

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Quality Control of 1,2-Benzenediol

Number of papers citing our products

Chemical structure

1,2-Benzenediol

3D structure

Chemical Properties of 1,2-Benzenediol

Cas No. 120-80-9 SDF Download SDF
PubChem ID 289 Appearance White powder
Formula C6H6O2 M.Wt 110.1
Type of Compound Phenols Storage Desiccate at -20°C
Synonyms 1,2-Benzenediol; 1,2-Dihydroxybenzene; 2-Hydroxyphenol; Pyrocatechin; Pyrocatechol
Solubility Soluble in water
Chemical Name benzene-1,2-diol
SMILES C1=CC=C(C(=C1)O)O
Standard InChIKey YCIMNLLNPGFGHC-UHFFFAOYSA-N
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.

Source of 1,2-Benzenediol

The heartwoods of Pseudolarix amabilis.

Biological Activity of 1,2-Benzenediol

Description1,2-Dihydroxybenzene can induce spontaneous convulsive activity in the anaesthetized mouse and produce myoclonic jerks in the rat. It regulated 5-Hydroxytryptamine (5-HT) levels.
Targets5-HT Receptor
In vivo

A pharmacological study of the spontaneous convulsive activity induced by 1,2-dihydroxybenzene (catechol) in the anaesthetized mouse.[Reference: WebLink]

Brit. J. Pharmacol., 1977, 61(3):433-9.


METHODS AND RESULTS:
1. The convulsive activity induced by catechol(1,2-Benzenediol) has been examined in anaesthetized mice either by determining the CD50 for the convulsions in drug-treated and control animals, or by studying the effects of various drugs on the total whole body activity. 2. The results indicate that catecholamines play no part in the mechanism of action of catechol. Drugs which alter cerebral catecholamine levels had no effect on the convulsions, nor did the alpha- and beta-adrenoceptor blocking drugs. 3. 5-Hydroxytryptamine (5-HT) could possibly be important, though results with drugs which either change brain 5-HT levels, or block 5-HT receptors were inconsistent. 4. gamma-Aminobutyric acid also appears not to be involved in the mechanism of action of catechol.
CONCLUSIONS:
5. The results strongly suggest that catechol primarily activates a central cholinergic system, in that muscarinic and nicotinic receptor blocking drugs inhibit, and anticholinesterases potentiate the convulsions.

Protocol of 1,2-Benzenediol

Kinase Assay

Carbonic anhydrase inhibitors: guaiacol and catechol derivatives effectively inhibit certain human carbonic anhydrase isoenzymes (hCA I, II, IX and XII).[Pubmed: 25373500]

J Enzyme Inhib Med Chem. 2015 Aug;30(4):586-91.

A series of phenolic compounds, including guaiacol, 4-methylguaiacol, 4-propylguaiacol, eugenol, isoeugenol, vanillin, syringaldehyde, 1,2-Benzenediol, 3-methyl catechol, 4-methyl 1,2-Benzenediol and 3-methoxy catechol were investigated for their inhibition of all the catalytically active mammalian isozymes of the Zn(2+)-containing CA (EC 4.2.1.1). All the phenolic compounds effectively inhibited human carbonic anhydrase isoenzymes (hCA I, II, IX and XII), with Kis in the range of 2.20-515.98 μM. The various isozymes showed diverse inhibition profiles. Among the tested phenolic derivatives, compounds 4-methyl 1,2-Benzenediol and 3-methoxy 1,2-Benzenediol showed potent activity as inhibitors of the tumour-associated transmembrane isoforms (hCA IX and XII) in the submicromolar range, with high selectivity. The results obtained from this research may lead to the design of more effective carbonic anhydrase isoenzyme inhibitors (CAIs) based on such phenolic compound scaffolds.

Animal Research

An analysis of the myoclonic jerks produced by 1, 2-dihydroxybenzene in the rat.[Reference: WebLink]

Electroencephalography & Clinical Neurophysiology, 1973, 35(6):589-601.


METHODS AND RESULTS:
In rats deeply anaesthetized with urethane, injection of 1,2 dihydroxybenzene (catechol; 60 mg/kg i.p.) produces a stimulus-sensitive state in which a variety of sensory stimuli, e.g., a brief electrical shock or mechanical tap applied to the periphery, or a binaural click, produce brief (myoclonic) muscular jerks. These jerks have been recorded electromyographically in the forelimb from the biceps and triceps brachii and in the hind limb from gastrocnemius and tibialis anterior. The myoclonic jerks produced in these muscles by electrical or mechanical stimulation of the corresponding paw consisted of three distinct components. The early, first response to electrical stimulation has a short consistent latency (4.3 ± 0.6 msec in the forelimb; 8.1 ± 0.9 msec in the hind limb), large amplitude and high probability of occurence. This first response represents a polysynaptic reflex elicited by stimulation of cutaneous afferents. It is not, however, a simple reflex since it could be recorded in direct antagonists at a similar latency. The first response persisted in the hind limb muscles with both chronic and acute spinal transection at T10-T12. The second response (13.4 ± 1.6 msec in the forelimb; 19.4 ± 3.7 msec in the hind limb) and the third response (40.0 ± 7.3 msec and 51.4 ± 7.3 msec respectively) were both abolished in the hind limb muscles by spinal transection. Records of single motor units in the tibial nerve showed that discharge of a single motoneurone can account for all three components of the reflex jerk. The second, and to a lesser extent, the third response were always reduced in amplitude when the first response was large. Conversely, large second responses were only recorded when the first response was small or absent.
CONCLUSIONS:
Catechol had no effect on the amplitude or latency of the afferent volley recorded at the dorsal root entry zone, but markedly potentiated both mono- and polysynaptic reflexes.

1,2-Benzenediol Dilution Calculator

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1,2-Benzenediol Molarity Calculator

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Preparing Stock Solutions of 1,2-Benzenediol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 9.0827 mL 45.4133 mL 90.8265 mL 181.653 mL 227.0663 mL
5 mM 1.8165 mL 9.0827 mL 18.1653 mL 36.3306 mL 45.4133 mL
10 mM 0.9083 mL 4.5413 mL 9.0827 mL 18.1653 mL 22.7066 mL
50 mM 0.1817 mL 0.9083 mL 1.8165 mL 3.6331 mL 4.5413 mL
100 mM 0.0908 mL 0.4541 mL 0.9083 mL 1.8165 mL 2.2707 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 1,2-Benzenediol

Reaction Kinetics of Catechol (1,2-Benzenediol) and Guaiacol (2-Methoxyphenol) with Ozone.[Pubmed:26053029]

J Phys Chem A. 2015 Jul 2;119(26):6759-65.

The kinetic reactions of 1,2-Benzenediol (catechol) and 2-methoxyphenol (guaiacol) with ozone were studied in a simulation chamber (8 m(3)) under dark conditions. The rate coefficients were measured at 294 +/- 2 K, atmospheric pressure and dry conditions (relative humidity, RH < 1%), except for 1,2-Benzenediol where they were also measured as a function of relative humidity (RH = 1-80%). The concentrations of organic compounds were followed by a PTR-ToF-MS for a continuous monitoring of gas-phase species. The O3 rate coefficients were obtained using both the pseudo-first-order and relative rate methods. The values (in cm(3) molecule(-1) s(-1)) determined for catechol and guaiacol under dry conditions are (13.5 +/- 1.1) x 10(-18) and (0.40 +/- 0.31) x 10(-18), respectively. The rate coefficient of catechol was found to be independent of RH below 20% and above 60%, whereas for RH between 20% and 60% it decreases with increasing RH. The determined rate coefficients have been used to evaluate the atmospheric lifetime of each compound with respect to O3. To our knowledge, this study represents the first determination of the ozone rate coefficient with guaiacol and is also the first kinetic investigation for the influence of the relative humidity on the oxygenated aromatic ozonolysis.

Carbonic anhydrase inhibitors: guaiacol and catechol derivatives effectively inhibit certain human carbonic anhydrase isoenzymes (hCA I, II, IX and XII).[Pubmed:25373500]

J Enzyme Inhib Med Chem. 2015;30(4):586-91.

Carbonic anhydrases (CAs) are widespread metalloenzymes in higher vertebrates including humans. A series of phenolic compounds, including guaiacol, 4-methylguaiacol, 4-propylguaiacol, eugenol, isoeugenol, vanillin, syringaldehyde, catechol, 3-methyl catechol, 4-methyl catechol and 3-methoxy catechol were investigated for their inhibition of all the catalytically active mammalian isozymes of the Zn(2+)-containing CA (EC 4.2.1.1). All the phenolic compounds effectively inhibited human carbonic anhydrase isoenzymes (hCA I, II, IX and XII), with Kis in the range of 2.20-515.98 muM. The various isozymes showed diverse inhibition profiles. Among the tested phenolic derivatives, compounds 4-methyl catechol and 3-methoxy catechol showed potent activity as inhibitors of the tumour-associated transmembrane isoforms (hCA IX and XII) in the submicromolar range, with high selectivity. The results obtained from this research may lead to the design of more effective carbonic anhydrase isoenzyme inhibitors (CAIs) based on such phenolic compound scaffolds.

Keywords:

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