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Guanidine hydrochloride

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Guanidine hydrochloride Basic information
description Protein Denaturation Uses Drug intermediates Preparation Purification of inclusion body proteins A cyclic guanidine hydrochloride capsules Reference quality standards Chemical properties Uses Production method References
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
Melting point 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
PH4.5-5.5 (100g/l, H2O, 20℃)
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
descriptionGuanidine hydrochloride is a strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant.It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.
Guanidine Hydrochloride is the hydrochloride salt form of guanidine, a strong basic compound with parasympathomimetic activity. Guanidine hydrochloride enhances the release of acetylcholine following a nerve impulse and potentiates acetylcholine actions on muscarinic and nicotinic receptors. It also appears to slow the rates of depolarization and repolarization of muscle cell membranes.
Guanidine Hydrochloride is a powerful, chaotropic agent which is widely used for purification of proteins and nucleic acids. Guanidine Hydrochloride is useful for denaturation and refolding of proteins as well as in the recovery of periplasmic proteins and isolation of RNA. At higher concentrations, this strong denaturant has been reported to solubilize denatured insoluble proteins such as inclusion bodies. When utilized at lower concentrations, Guanidine Hydrochloride is noted to be useful in prompting the refolding of denatured proteins. Guanidine Hydrochloride is also been reported to allow return of enzymatic activity in protocols using Guanidine Hydrochloride as a first step. Guanidine Hydrochloride is an inhibitor of RNase.
Guanidine hydrochloride is used for purification of proteins and nucleic acids. It can be used as a medicine, organic synthesis intermediate and is used in dyes. It acts as an intermediate in the preparation of sulfadiazine, which is an important raw material for sulfamethyldiazine, sulfamethazine and folic acid. It is utilized in the synthesis of 2-amino-pyrimidine, 2-amino-6-methyl-pyrimidine and 2-amino-4,6-dimethyl-pyrimidine. Also used in RNA isolation to dissociate nucleoproteins and inhibit RNase.
Protein DenaturationGuanidine Hydrochloride (GdnHCl) is a better denaturant than urea.It should normally give higher and lower values for m and for Cm, respectively, but identical deltaG° values. Since m values in both denaturants can be predicted/estimated from the size of the protein (Myers et al., 1995) and delatG° should not change, yes it is possible-in principle-to predict Cm in one denaturant, knowing its value in the other.
but to have a general correlation co-efficient is almost impossible as every protein has unique folding. Though such co-relation may be found for a special protein fold, but what purpose it may serve apart from giving a tentative idea that GdnHCl or urea may be a better denaturant! If you are looking for even better denaturant than Gdn HCl then use GdnSCN, it is better and more effective.
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.
Purification of inclusion body proteinsDenaturing 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
UsesGuanidine has a good bacterial and fungicidal efficacy when used in low concentration and can also be used as disinfectant.
UsesUsed to synthesis medicine, pesticide, dye and other organic compound, is the important material to make sulfanilamide medicine and folacin, and can be used as anti-static agent of compound fibre.
DefinitionChEBI: An aminocarboxamidine, the parent compound of the guanidines.
Tag:Guanidine hydrochloride(50-01-1) Related Product Information
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