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Guanidine hydrochloride

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Guanidine hydrochloride Basic information
Uses Drug intermediates Preparation The role of urea and guanidine hydrochloride in the purification of protein inclusion bodies A cyclic guanidine hydrochloride capsules Reference quality standards Chemical properties Uses Production method
Product Name:Guanidine hydrochloride
Synonyms:guanidine,monohydrochloride;guanidinechloride;Guanidinemonohydrochloride;guanidiniumhydrochloride;usafek-749;CARBAMIDINE HYDROCHLORIDE;IMINOUREA HYDROCHLORIDE;GUANIDINIUM CHLORIDE
Product Categories:Pharmaceutical Intermediates;Miscellaneous Biochemicals;proteinmod;Inhibitors
Mol File:50-01-1.mol
Guanidine hydrochloride Structure
Guanidine hydrochloride Chemical Properties
mp 180-185 °C(lit.)
density 1.18 g/mL at 25 °C(lit.)
refractive index n20/D 1.465
storage temp. Store at RT.
solubility H2O: 6 M, clear, colorless
Water Solubility 2280 g/L (20 ºC)
Sensitive Hygroscopic
Merck 14,4562
BRN 3591990
Stability:Stable. Hygroscopic. Incompatible with strong oxidizing agents.
CAS DataBase Reference50-01-1(CAS DataBase Reference)
EPA Substance Registry SystemGuanidine, monohydrochloride(50-01-1)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/38
Safety Statements 26-36-22
WGK Germany 1
RTECS MF4300000
HS Code 29252000
MSDS Information
Guanidine hydrochloride English
ACROS English
SigmaAldrich English
ALFA English
Guanidine hydrochloride Usage And Synthesis
UsesGuanidine hydrochloride is used in RNA isolation to dissociate nucleoproteins and inhibit RNase.
Strong chaotropic agent useful for the denaturation and subsequent refolding of proteins. This strong denaturant can solubilize insoluble or denatured proteins such as inclusion bodies. This can be used as the first step in refolding proteins or enzymes into their active form. Urea and dithiothreitol (DTT) may also be necessary.
Drug intermediatesGuanidine hydrochloride drug used primarily as an intermediate in the manufacture of sulfadiazine, an important raw material sulfamethyldiazine, sulfamethazine and folic acid.
Guanidine hydrochloride (or guanidine nitrate) and ethyl cyanoacetate reaction, cyclization of 2,4-diamino-6-hydroxy pyrimidine, folic acid for the synthesis of antianemic. Furthermore guanidine hydrochloride also used synthetic anti-static agent.
PreparationIn Dicyanodiamide and ammonium (Ammonium chloride) as raw material, melt reaction at 170-230 ℃, guanidine hydrochloride obtained crude, refined products.
The role of urea and guanidine hydrochloride in the purification of protein inclusion bodiesDenaturing agents (urea and guanidine hydrochloride) can break the hydrogen bond in the protein structure, which increases the solubility of non-polar molecules including the side chains of amino acid, reducing the hydrophobic interaction; Urea can also deep into the interior of the protein molecule to affect the close packing state of protein molecules. In addition, detergents, organic solvents, heavy metals, heat, mechanical forces, freezing, ultrasound, high pressure, radiation, etc. all can cause protein denaturation. These kinds of denaturation are only related to disrupting the secondary bond interaction such as the hydrogen bond, salt bond, hydrophobic interactions, van der Waals interactions without breaking the covalent bonds. Some denatured proteins can automatically restore into its natural conformation after the denaturation factors have been removed, a phenomenon known as protein refolding (re-naturation), namely that re-folding in the field of protein folding research.
Inclusion body protein purification
Most conditions are at pH8, usually use strong denaturing agents such as urea (6-8mol/L), guanidine hydrochloride (Gdn-HCl 5~8 mol/L or 6mol/L), to disrupt any kinds of chemical bonds within or between protein molecules through the interactions between ions, and thus stretching the polypeptide. In general, Gdn-HCl is better than urea due to that Gdn-HCl is stronger denaturant than urea, which enables the dissolution of inclusion bodies which cannot be dissolved by urea. Moreover, urea has an issue that it decomposed isocyanate can cause the formylation of the free amino groups of the polypeptide, especially for long-term incubation at alkaline pH condition. Using detergents such as SDS, n-hexadecyl-trimethyl ammonium chloride, or Sarkosyl, etc., which can disrupt the hydrophobic bonding within the protein, can also dissolve the inclusion body proteins. Moreover, we can use TritonX-100 to dissolve the protein inclusion bodies of Zymononas mobilis levansucrase. In addition, for the cysteine-containing proteins, their isolated inclusion bodies generally contain a number of inter-chain disulfide bonds and non-active disulfide bonds within chain. For these inclusion bodies, we can apply some organic solution, alkaline environment (greater than 9) or acid (70% formic acid) to dissolve them.
We need to add a reducing agent in denaturing solution such as 2-mercaptoethanol (β-ME), dithiothreitol (of DTT), dithioerythritol alcohols, reduced glutathione (GST), and the cysteine. Concentration of the reducing agent is generally 50-100mM β-ME or DTT. Some literature also use 5mM. The concentration of the reducing agent has nothing to do with the number of the disulfide bonds. For proteins without disulfide bonds, adding or not reducing reagent doesn’t make any difference, such as improving the dissolution of inclusion bodies of bovine growth hormone. For the inclusion bodies of certain target proteins without disulfide bonds, sometimes it is still necessary to use a reducing agent which may be due to that disulfide bonds-containing impure protein affects the dissolution of inclusion bodies. Also we need to add a metal chelating agent such as EDTA or EGTA, to chelate metal ions such as Cu2+, Fe2+ prevent the oxidation reaction between the reduced thiol groups with them. After the dissolution of denaturant, protein will lose its biological activity.
A cyclic guanidine hydrochloride capsules[Properties]capsules, yellow powder inside it.
[Toxicology] This product is a broad-spectrum antimicrobial agent which has a bactericidal effect when applied at high concentrations. The product has certain antibacterial effects on Streptococcus pneumoniae, hemolytic streptococcus, staphylococcus and some grass lotus bacteria, Clostridium perfringens, Bacillus anthracis, Yersinia pestis, diphtheria, tetanus, Brucella spp, Haemophilus influenzae, bending spp., and Vibrio cholerae. It also has inhibitory effects on Rickettsia, mycoplasma, Chlamydia, spirochetes, and some protozoa. However, Enterobacteriaceae such as Escherichia coli, Klebsiella, Salmonella, and Shigella are mostly resistant to this product. This product has a better effect on Gram-positive bacteria than gram-negative bacteria, but Enterococcus is resistant to it. Others species such as Actinomyces, Bacillus anthracis, Listeria monocytogenes bacteria, Clostridium spp and Nocardia, are also sensitive to the chemical. Neisseria gonorrhoeae which is resistant to this product is also resistant to tetracycline. The product has a certain antibacterial effect on Neisseria gonorrhoeae and Neisseria meningitidis with a certain antibacterial activity, but penicillin-resistant Neisseria gonorrhoeae is also resistant to tetracycline. This mechanism of action of this product is that it can specifically bind to the A site of bacterial 30S ribosomal subunit, blocking the attach of aminoacyl-tRNA into this site, and thus blocking the growth of the peptide chain and the overall protein synthesis.
[Pharmacokinetics] This product has a high solubility in water, and can be rapidly absorbed after oral administration. The blood concentration reaches highest within 3 hours with effective blood concentration being maintained for 12 hours. Compared with other tetracyclines, its main feature is its great affinity to bronchial and lung tissue. It has a much higher concentration in the bronchus, lung tissue and bronchial secretions than comparable amount tetracycline hydrochloride after orally administration. Its concentration in the blood can be maintained at a higher level and longer period than tetracycline. It is mainly excreted by urine in its active form.
[Indications]For respiratory infections caused by sensitive strains.
[Dosage] Oral administration. Day 1.2g (12 grains), three to four times daily.
[Specification] 0.1g (10 million units).
[Storage] sealed and kept in a dry, cool and dark place.
Reference quality standardsName of Project Specifications
Pharmaceutical grade industrial grade
Appearance white crystal; white crystal
Content > 99% 99.5%
Ammonium <0.3% 0.5%
Water Insoluble substance <0.1% 0.1%
Moisture <0.3% 0.3%
Ash <0.05% 0.05%
Water-soluble test qualified; qualified
Melting range °C 184-188; 182-188
Absorbance (UV wavelength 260NM) 《0.04
Absorbance (UV wavelength 280NM) 《0.02
PH value (4% aqueous solution) 6.4 ± 0.2 6.4 ± 0.2
Chemical propertiesWhite or yellowish lumps; Solubility in 20 °C: 200g/100g in water; 76g/100g in methanol; 24g/ 100g in ethanol; Almost insoluble in acetone, benzene and ether.
The above information is edited by the Chemicalbook of Dai Xiongfeng.
Uses1. For organic synthesis and pharmaceutical industry.
2. Mainly used as a pharmaceutical intermediate; an important raw material for producing sulfadiazine, sulfamethyldiazine, sulfamethazine and folic acid.
3. Used as intermediates for synthesis of medicine, pesticides, dyes and other organics. For synthesis of 2-amino-pyrimidine, 2-amino-6-methyl-pyrimidine, and 2-amino-4,6-dimethyl-pyrimidine. A intermediate for producing sulfadiazine, sulfamethyldiazine, and sulfamethazine. Guanidine hydrochloride (or guanidine nitrate) can be reacted with ethyl cyanide for cyclization into 2,4-diamino-6-hydroxy-pyrimidine. This is for synthesis of anti-anemia drugs: folic acid. It can also be used for the synthesis of anti-static agent of synthetic fiber.
Production methodUse dicyandiamide and ammonium salts (ammonium chloride) as raw material. Perform melting reaction at 170-230 °C to obtain crude guanidine hydrochloride was crude. Refine to get the final product.
Chemical PropertiesWhite cryst. powder
UsageGuanidine has a good bacterial and fungicidal efficacy when used in low concentration and can also be used as disinfectant.
Tag:Guanidine hydrochloride(50-01-1) Related Product Information
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