10040-45-6

Basic information

• Product Name: Sodium picosulfate
• Synonyms: 4,4'-(2-Pyridinylmethylene)bis(phenol)bis(sulfuric acid sodium) salt;DA 1773;DA-1773;LA 391;C13072;Sodium Picosulfate (50 mg);Bisacodyl IMpurity D;SodiuM Picosulphate USP
• CAS NO: 10040-45-6
• Molecular Formula: C₁₈H₁₃NO₈S₂*2Na
• Molecular Weight: 481.41
• EINECS: 233-120-9
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Inhibitors
• Mol File: 10040-45-6.mol

Chemical Properties

• Melting Point: 283-286°C
• Appearance: gray powder complex
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility: Freely soluble in water, slightly soluble in ethanol 96 per cent.
• Stability: Hygroscopic
• CAS DataBase Reference: Sodium picosulfate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium picosulfate(10040-45-6)
• EPA Substance Registry System: Sodium picosulfate(10040-45-6)

Safety Data

• Hazardous Substances Data: 10040-45-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Sodium picosulfate is used as a stimulant laxative for the treatment of constipation. It works by increasing the frequency and force of peristalsis, which helps to move the contents of the colon more quickly and effectively. This results in a more rapid and complete evacuation of the bowel, providing relief for individuals suffering from constipation.
Used in Medical Diagnostics:
In the field of medical diagnostics, sodium picosulfate is used for the evaluation of the colon. It stimulates bowel movements following hydrolysis by colon bacteria, which can be particularly useful in preparing patients for colonoscopies or other diagnostic procedures that require a clear view of the colon's interior. By promoting bowel movements, sodium picosulfate helps to ensure that the colon is clean and free of any obstructions that could interfere with the diagnostic process.
Used in Gastrointestinal Health:
Sodium picosulfate is also used to address gastrointestinal health issues related to constipation. It can be prescribed to patients who experience infrequent or difficult bowel movements, providing relief and improving overall digestive health. Additionally, sodium picosulfate may be used in combination with other medications or treatments to manage more complex gastrointestinal conditions.

Originator

Guttalax, De Angelini, Italy ,1967

Therapeutic Function

Laxative

InChI:InChI=1/C18H15NO8S2.2Na/c20-28(21,22)26-15-8-4-13(5-9-15)18(17-3-1-2-12-19-17)14-6-10-16(11-7-14)27-29(23,24)25;;/h1-12,18H,(H,20,21,22)(H,23,24,25);;/q;2*+1/p-2

Synthetic route

4,4'-(2-pyridylmethylene)diphenol (603-41-8) → Guttalax (10040-45-6)

Conditions	Yield
Stage #1: 4,4'-(2-pyridylmethylene)diphenol With pyridine; chlorosulfonic acid at 0 - 20℃; for 5h; Stage #2: With sodium hydroxide Concentration; Cooling with ice;	86.4%
Stage #1: 4,4'-(2-pyridylmethylene)diphenol With pyridine; chlorosulfonic acid at 35 - 40℃; for 3h; Flow reactor; Stage #2: With sodium hydroxide	59.9%
Stage #1: 4,4'-(2-pyridylmethylene)diphenol With pyridine; chlorosulfonic acid at 10 - 25℃; for 12h; Inert atmosphere; Large scale; Stage #2: With water; sodium hydroxide at 0℃; pH=11; pH-value; Inert atmosphere; Large scale;	2.1 kg

1-bromo-4-methoxy-benzene (104-92-7) → Guttalax (10040-45-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 1 h / 20 - 65 °C / Inert atmosphere; Large scale 1.2: 4 h / 10 - 20 °C / Inert atmosphere; Large scale 2.1: hydrogen iodide; acetic acid / 6 h / 100 °C / Large scale 3.1: pyridine; chlorosulfonic acid / 12 h / 10 - 25 °C / Inert atmosphere; Large scale 3.2: 0 °C / pH 11 / Inert atmosphere; Large scale View Scheme

ethyl-2-picolinate (2524-52-9) → Guttalax (10040-45-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 1 h / 20 - 65 °C / Inert atmosphere; Large scale 1.2: 4 h / 10 - 20 °C / Inert atmosphere; Large scale 2.1: hydrogen iodide; acetic acid / 6 h / 100 °C / Large scale 3.1: pyridine; chlorosulfonic acid / 12 h / 10 - 25 °C / Inert atmosphere; Large scale 3.2: 0 °C / pH 11 / Inert atmosphere; Large scale View Scheme

Guttalax (10040-45-6) + β‐cyclodextrin (7585-39-9) → C18H13NO8S2(2-)*2Na(1+)*C42H70O35

Conditions	Yield
In water at 25℃;

Guttalax (10040-45-6) → 4-((4-hydroxyphenyl)(pyridin-2-yl)methyl)phenyl hydrogen sulfate (51264-33-6)

Conditions	Yield
With water at 40℃; for 730.5h; Temperature;

Guttalax (10040-45-6) → 4-((4-hydroxyphenyl)(pyridin-2-yl)methyl)phenyl hydrogen sulfate (51264-33-6) + 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
With water at 40℃; for 730.5h;

Guttalax (10040-45-6) → 4-((4-hydroxyphenyl)(pyridin-2-yl)methyl)phenyl hydrogen sulfate (51264-33-6) + 4,4'-(2-pyridylmethylene)diphenol (603-41-8) + (hydroxy(pyridin-2-yl)methylene)bis(4,1-phenylene) bis(sulfate)

Conditions	Yield
With water at 40℃; for 4383h; Temperature;

Guttalax (10040-45-6) → 4-((4-hydroxyphenyl)(pyridin-2-yl)methyl)phenyl hydrogen sulfate (51264-33-6) + (hydroxy(pyridin-2-yl)methylene)bis(4,1-phenylene) bis(sulfate)

Conditions	Yield
With water at 40℃; for 2191.5h; pH=4.5; pH-value; Temperature;

Upstream product

• 2524-52-9 ethyl-2-picolinate 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 603-41-8 4,4'-(2-pyridylmethylene)diphenol 

Downstream Products

• 51264-33-6 4-((4-hydroxyphenyl)(pyridin-2-yl)methyl)phenyl hydrogen sulfate 
• 603-41-8 4,4'-(2-pyridylmethylene)diphenol 

Relevant articles and documents

Preparation method of sodium picosulfate

The invention belongs to the technical field of medicines, and relates to a preparation method of sodium picosulfate, in particular to condensation of pyridine -2 - formaldehyde and phenol under an acidic condition, and the obtained intermediate 4,4 ' - (2 - pyridinmethylene) - bisphenol uses sulfamic acid as a sulfonating agent. The method is relatively simple in process operation and high in sample purity.

Method for preparing high-purity sodium picosulfate intermediate and sodium picosulfate

The invention discloses a method for preparing high-purity sodium picosulfate and an intermediate thereof. The method comprises the following steps: (1) dropwise adding concentrated sulfuric acid and 2-pyridylaldehyde into an acetonitrile solution of phenol in sequence for reaction; (2) adjusting to be alkaline after reaction quenching, neutralizing, dispersing and crystallizing, and refining a crude product by using organic alcohol; (3) adding the intermediate into a pyridine solution of chlorosulfonic acid, washing off pyridine by using acetone after the reaction is finished, treating into sodium salt by using an alkali, concentrating until dryness, extracting by using hot methanol, adding ethyl acetate for crystallization, filtering and drying to obtain a sodium picosulfate crude product; and (4) thermally extracting the crude product with absolute ethyl alcohol, adding a proper amount of purified water, cooling and crystallizing to obtain the sodium picosulfate monohydrate. According to the method, the high-purity intermediate and the sodium picosulfate monohydrate can be stably obtained by controlling the content of the isomer in the intermediate.

A process for preparing sodium new method (by machine translation)

The invention relates to a method for preparing (V) indicated by the sodium of the method, the method comprises the following steps: (a) in formula (I) indicated by the 2 - picolinic ester as the starting material, as shown in formula (II) of 4 - halogenated phenyl ether in the formula (III) Grignard reaction indicated by the 4', 4" - dialkoxy diphenyl - (2 - pyridine) - methanol (compound III). (B) 4 ', 4 "- dialkoxy diphenyl - (2 - pyridine) - methanol (compound III) in the Lewis acid under the action of removing a water molecule and alkoxy alkyl, formula (IV) as shown by a 4', 4" - dihydroxy phenyl - (2 - pyridine) - methane (compound IV). (C) 4', 4" - dihydroxy phenyl - (2 - pyridine) - methane with chlorosulfuric acid in sulfuric acid esterification reaction, sodium hydroxide after treatment, to obtain crude sodium, by recrystallization to obtain high-purity sodium (compound V). The present invention provides a kind of existing technology with the different sodium new preparation method, the method is simple in operation, the atom economy is high, is suitable for industrial production. (by machine translation)

A process for preparing sodium method

The invention discloses a method for preparing sodium picosulfate, which comprises the following steps: 1) preparing a 2-chlorophenol-ethanedioic acid mixture M and a 2-pyridylaldehyde-concentrated sulfuric acid mixture N; 2) dropwisely adding the mixture M obtained in the step (1) into the mixture N at 0-10 DEG C, continuing reaction at 20-30 DEG C, regulating the pH value to 8 with a sodium hydroxide solution, carrying out vacuum filtration, and washing with water to obtain a 3,3'-dichloro-4,4'-(pyridyl-2-yl-methylene)biphenol crude product; 3) dissolving the crude product in a 4M sodium hydroxide solution, adding a nickel aluminum alloy, stirring to react, filtering to take the filtrate, regulating the pH value with 10% acetic acid, filtering, washing with water, recrystallizing with methanol, filtering, and carrying out vacuum drying to obtain 4,4'-(pyridyl-2-yl-methylene)biphenol; and 4) dissolving the 4,4'-(pyridyl-2-yl-methylene)biphenol in pyridine, dropwisely adding chlorosulfonic acid at 0-10 DEG C to react, quenching with ice water, regulating the pH value with a sodium hydroxide solution, extracting with dichloromethane, concentrating the water phase under reduced pressure, recrystallizing with methanol, filtering, and carrying out vacuum drying. The method has the advantages of higher sodium picosulfate yield and fewer byproducts.