36589-58-9

Basic information

• Product Name: 1,3-PROPANEDISULFONIC ACID DISODIUM SALT
• Synonyms: 1,3-Propanedisulfonic acid disodium salt, 99%(dry wt.), water ;1,3-Propanedisulfonic acid, disodium salt,99%;Eprodisate disodium;NC 503;1,3-Propanedisulfonic disodium;Eprodisate Sodium;1,3-PROPANEDISULFONIC ACID DISODIUM SALT;DISODIUM PROPANE-1,3-DISULFONATE
• CAS NO: 36589-58-9
• Molecular Formula: C₃H₆O₆S₂*2Na
• Molecular Weight: 248.19
• Product Categories: Organic Building Blocks;Sulfonic/Sulfinic Acid Salts;Sulfur Compounds
• Mol File: 36589-58-9.mol

Chemical Properties

• Melting Point: >300°C
• Appearance: White coarse powder
• Density: 1.773 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Partially soluble in cold water, hot water.
• Sensitive: Hygroscopic
• BRN: 3767479
• CAS DataBase Reference: 1,3-PROPANEDISULFONIC ACID DISODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-PROPANEDISULFONIC ACID DISODIUM SALT(36589-58-9)
• EPA Substance Registry System: 1,3-PROPANEDISULFONIC ACID DISODIUM SALT(36589-58-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 36589-58-9(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1,3-Propanedisulfonic acid disodium salt is used as a keratolytic agent for promoting the shedding of dead skin cells, which is particularly beneficial in the treatment of various skin conditions and disorders.
2. Used in Chemical Synthesis:
1,3-Propanedisulfonic acid disodium salt serves as a reactant in the synthesis of cadmium(II) bipyridine complex metal-organic frameworks with alkanedisulfonates and alkylenedisulfonate inorganic-organic hybrid materials. These materials have potential applications in various fields, including gas storage, catalysis, and drug delivery.
3. Used in Biomedical Research:
1,3-Propanedisulfonic acid disodium salt is used as a glycosaminoglycan mimetic, which is involved in pharmacological studies for the treatment of amyloid A amyloidosis. This application highlights its potential in contributing to the development of novel therapeutic strategies for managing this disease.

InChI:InChI=1/C3H8O6S2.2Na/c4-10(5,6)2-1-3-11(7,8)9;;/h1-3H2,(H,4,5,6)(H,7,8,9);;/q;2*+1/p-2

Synthetic route

4,4,8,8-tetraoxo-4λ6,8λ6-dithia-undecanedinitrile (90566-47-5) → sodium α,ω-alkanedisulfonate (36589-58-9)

Conditions	Yield
With sodium methylate In methanol for 25h;	85%

1,3-dibromo-propane (109-64-8) → sodium α,ω-alkanedisulfonate (36589-58-9)

Conditions	Yield
With sodium sulfite In not given Heating;
With sodium sulfite Heating;
With sodium sulfite In water Substitution; sulfonation; Heating;
With sodium sulfite

neodymium(III) nitrate hexahydrate + water (7732-18-5) + sodium α,ω-alkanedisulfonate (36589-58-9) + sodium hydroxide (1310-73-2) → C3H6O6S2(2-)*4HO(1-)*2Nd(3+)*2H2O

Conditions	Yield
at 150℃; for 72h; pH=7; Autoclave; High pressure;	81%

4,4'-bipyridine (553-26-4) + cadmium(II) nitrate tetrhydrate + sodium α,ω-alkanedisulfonate (36589-58-9) → [Cd(H2O)4(4,4'-bipyridine)][1,3-propanedisulfonate]

Conditions	Yield
In water High Pressure; mixt. Cd(NO3)2*4H2O, PDSNa2, 4,4'-bipy and water was heated in Teflon lined autoclave at 180°C for 3 days; react. mixt. was cooled to room temp. at 6°C/h, ppt. was filteredand rinsed with water/acetone; elem. anal.;	70.5%

sodium α,ω-alkanedisulfonate (36589-58-9) → barium 1,3-propanedisulfonate (82203-69-8)

Conditions	Yield
With barium chloride monohydrate In water at 80℃; for 2h;	62%
With barium dihydroxide; ion-exchange resin Multistep reaction;

sodium α,ω-alkanedisulfonate (36589-58-9) → propane-1,3-disulfonic acid ; calcium salt (82203-68-7)

Conditions	Yield
With calcium hydroxide; ion-exchange resin Multistep reaction;

sodium α,ω-alkanedisulfonate (36589-58-9) → C3H6O6S2(2-)*2H2O*Mg(2+)

Conditions	Yield
With ion-exchange resin; magnesium oxide Multistep reaction;

6C45H30N10*12Ag(1+)*12C2F6NO4S2(1-) + sodium α,ω-alkanedisulfonate (36589-58-9) → 6C45H30N10*12Ag(1+)*10C2F6NO4S2(1-)*C3H6O6S2(2-)

Conditions	Yield
In [D3]acetonitrile at 20℃; for 18h; Inert atmosphere; Darkness;

lanthanum(III) nitrate hexahydrate + sodium α,ω-alkanedisulfonate (36589-58-9) → C3H6O6S2(2-)*4HO(1-)*2La(3+)*2H2O

Conditions	Yield
With hexamethylenetetramine In water at 100 - 120℃; Inert atmosphere;

Upstream product

• 109-64-8 1,3-dibromo-propane 
• 90566-47-5 4,4,8,8-tetraoxo-4λ⁶,8λ⁶-dithia-undecanedinitrile 

Downstream Products

• 20686-91-3 1,3-propanedisulfonyl dichloride 

Relevant articles and documents

Short-chain aliphatic polysulfonates inhibit the entry of Plasmodium into red blood cells

Several steps in the pathogenesis of a Plasmodium falciparum infection depend on interactions of parasite surface proteins with negatively charged sugars on the surface of host cells such as sialate residues or glycosaminoglycans. For these reasons, our previous studies examining agents that interfere with heparan sulfate-protein binding during amyloidogenesis suggested that short-chain aliphatic polysulfonates may prove useful as antimalarial agents. A series of related polysulfonates were synthesized and assessed both in tissue culture with the asexual stages of P. falciparum in human red blood cells and in vivo by use of Plasmodium berghei infections in mice. Poly (vinylsulfonate sodium salt) (molecular weight range, 1,500 to 3,000) proved effective in interfering with P. falciparum merozoite entry into human red blood cells and significantly delaying the increase in the level of P. berghei parasitemia in mice. The concept that anionic molecules that mimic large polysaccharide structures may have antimalarial properties has been suggested and examined previously. Our results suggest that related anionic agents [poly (vinylsulfonate sodium salt)-like molecules] orders of magnitude smaller than those previously considered may prove useful in abrogating merozoite entry into erythrocytes and may potentially block sporozoite entry into liver cells. Structure-activity studies conducted to enhance these properties may provide compounds with scope for significant further analysis and development.

METHODS, COMPOUNDS, AND COMPOSITIONS FOR DELIVERING 1,3-PROPAN ED ISULFONIC ACID

The invention relates to methods, compounds, and compositions for delivering 1,3-propanedisulfonic acid (1,3PDS) in a subject, preferably a human subject. The invention encompasses compounds that will yield or generate 1,3PDS, either in vitro or in vivo. The invention also relates to sulfonate ester prodrugs of 1,3PDS as well as Gemini dimmers and oligomers of 1,3PDS for the prevention or treatment of associated diseases and conditions.

Method for treating amyloidosis

Therapeutic compounds and methods for inhibiting amyloid deposition in a subject, whatever its clinical setting, are described. Amyloid deposition is inhibited by the administration to a subject of an effective amount of a therapeutic compound comprising an anionic group and a carrier molecule, or a pharmaceutically acceptable salt thereof, such that an interaction between an amyloidogenic protein and a basement membrane constituent is inhibited. Preferred anionic groups are sulfonates and sulfates. Preferred carrier molecules include carbohydrates, polymers, peptides, peptide derivatives, aliphatic groups, alicyclic groups, heterocyclic groups, aromatic groups and combinations thereof.

Method for treating amyloidosis

Therapeutic compounds and methods for inhibiting amyloid deposition in a subject, whatever its clinical setting, are described. Amyloid deposition is inhibited by the administration to a subject of an effective amount of a therapeutic compound comprising an anionic group and a carrier molecule, or a pharmaceutically acceptable salt thereof, such that an interaction between an amyloidogenic protein and a basement membrane constituent is inhibited. Preferred anionic groups are sulfonates and sulfates. Preferred carrier molecules include carbohydrates, polymers, peptides, peptide derivatives, aliphatic groups, alicyclic groups, heterocyclic groups, aromatic groups and combinations thereof.

Method for treating amyloidosis

Therapeutic compounds and methods for inhibiting amyloid deposition in a subject, whatever its clinical setting, are described. Amyloid deposition is inhibited by the administration to a subject of an effective amount of a therapeutic compound comprising an anionic group and a carrier molecule, or a pharmaceutically acceptable salt thereof, such that an interaction between an amyloidogenic protein and a basement membrane constituent is inhibited. Preferred anionic groups are sulfonates and sulfates. Preferred carrier molecules include carbohydrates, polymers, peptides, peptide derivatives, aliphatic groups, alicyclic groups, heterocyclic groups, aromatic groups and combinations thereof.

Method for treating amyloidosis

Therapeutic compounds and methods for inhibiting amyloid deposition in a subject, whatever its clinical setting, are described. Amyloid deposition is inhibited by the administration to a subject of an effective amount of a therapeutic compound comprising an anionic group and a carrier molecule, or a pharmaceutically acceptable salt thereof, such that an interaction between an amyloidogenic protein and a basement membrane constituent is inhibited. Preferred anionic groups are sulfonates and sulfates. Preferred carrier molecules include carbohydrates, polymers, peptides, peptide derivatives, aliphatic groups, alicyclic groups, heterocyclic groups, aromatic groups and combinations thereof.

Detoxification of paraquat poisoning: Effects of alkylsulfates and alkylsulfonates on paraquat poisoning in mice and rats

The study revealed that high molecular polyvinyl sulfate (PVP) or sulfonate (PVS), and low molecular alkyldisulfonates (NaO3S(CH2)(n)SO3Na, n = 2-5: EDS, TDS, BDS and PDS) can alleviate acute toxicity of the herbicide, paraquat dichloride (PQ) in mice. Their activity as antidotes and the mode of the action varied depending on molecular size. The survival rate for mice receiving PQ at 200 mg/kg alone was increasingly improved when the dose of antidotes was increased from 8 to 10 times the dose of PQ; all the test compounds, except EDS (70% survival), achieved a survival rate of 100%. When test compounds were orally dosed to mice in a mixture with PQ, they improved LD50 of PQ alone. With the low molecular compounds EDS, TDS, BDS and PDS, the value increased to about 2 to 3 times (300-458 mg/kg) over that of PQ alone (140 mg/kg). With high molecular PVS and PVP, the combination reached about a 7 fold (900-1000 mg/kg) increase in LD50 value. The formation of lipid peroxide in lungs of rats due to PQ tended to be suppressed by concomitant administration of carbohydrate sulfate (DS and GS). PVP, BDS and TDS were more effective in depressing synthesis of lipid peroxide than DS or GS in the lungs, although BDS and TDS were less effective in suppressing PQ absorption from the rat small intestine than DS, GS or PVP. The results of these experiments indicate that the main mechanism for the detoxification of a high molecular alkylsulfate or sulfonate, and a low molecular alkyldisulfonate must be suppression of PQ absorption from the intestine, similar to that of carbohydrate sulfate. In addition, a low molecular alkyldisulfonate (BDS and TDS) was also proved to be significantly effective in suppressing the formation of lipid peroxide in the lungs.

Hydrates of Organic Compounds. XVI. Determination of the Melting Points and Hydration Numbers of the Hydrates of Tetrabutyl(or Tetraisopentyl)ammonium Alkanesulfonates

The solid liquid phase diagrams of binary mixtures of water with tetraisopentylammonium alkanesulfonates, (n=1-8), bis(tetrabutylammonium) alkanedisulfonates, 2 (n=2-5), and with bis(tetraisopentylammonium) alkanedisulfonates, 2 (n=2-5), were examined in order to confirm the formation of hydrates.For all of the sulfonates examined the formation of hydrates has been newly confirmed.The hydrates of the tetraisopentylammonium alkanesulfonates have hydration numbers of around 37-40 and fairly high melting points (lie between 13 and 19 deg C).The typical hydrates formed by the bis(tetrabutylammonium) alkanedisulfonates have hydration numbers of around 52 and those by the bis(tetraisopentylammonium) alkanedisulfonates around 76.The former disulfonate hydrates have low melting points (between 1.0 and 10 deg C).However, the latter disulfonate hydrates have fairly high melting points (between 13 and 18 deg C).A salt with n=4 forms the most stable hydrate for both series of alkanedisulfonates.Judging from the hydration numbers and melting points, these hydrates seem to be clathrate-like.

Precise Conductimetric Studies on Aqueous Solutions of 2:2 Electrolytes. Part 3. - Detailed Study of Individual Electrolytes

This paper reports precise conductance values for dilute (-3) aqueous solution of twenty-three 2:2 salts at 25 deg C.Alkaline earth metal sulfates, thiosulphates, dithionates, tetrathionates, ethyl-, n-propyl-, n-butyl-disulphonates and acetylenedicarboxylates were studied.The results are analysed by means of the Lee-Wheathon conductance equation in terms of the limiting molar conductivity, Λ0, the association constant, KA, and the association distance, R.The interpretation of these parameters is discussed and the values compared with previous work on these and similar systems.