Docusate Sodium

Catalog Number	ACM577117-2
CAS	577-11-7
Structure
Description	Docusate, also known as docusate salts or dioctyl sulfosuccinate, is a laxative used to treat constipation. It is considered a good choice in children who have hard feces. For constipation due to the use of opiates it may be used with a stimulant laxative. It can be taken by mouth or rectally. Usually it works in one to three days.Side effects are uncommon. Rarely there may be abdominal cramps or diarrhea. Long term use may cause poor bowel function. Docusate is acceptable during pregnancy and breastfeeding. It is a laxative of the stool softener type and works by allowing more water to be absorbed by the feces. It typically comes in the form of a sodium, calcium, or potassium salts.It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system. It is available as a generic medication and is not very expensive. In the United States one hundred doses are about 14 USD. Dioctyl sodium sulfosuccinate is also used as a food additive, emulsifier, dispersant, and wetting agent, among others.
Synonyms	Docusate sodium salt; Sulfosuccinic acid bis(2-ethylhexyl) ester sodium salt
IUPAC Name	sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate
Molecular Weight	444.56
Molecular Formula	C20H37NaO7S
Canonical SMILES	CCCCC(CC)COC(=O)CC(C(=O)OCC(CC)CCCC)S(=O)(=O)[O-].[Na+]
InChI	InChI=1S/C20H38O7S.Na/c1-5-9-11-16(7-3)14-26-19(21)13-18(28(23,24)25)20(22)27-15-17(8-4)12-10-6-2;/h16-18H,5-15H2,1-4H3,(H,23,24,25);/q;+1/p-1
InChI Key	APSBXTVYXVQYAB-UHFFFAOYSA-M
Melting Point	173-179 °C(lit.)
Flash Point	199ºC
Purity	≥98.0%
Density	1.1g/ml
Solubility	SOL IN WATER (G/L): 15 (25 °C), 23 (40 °C), 30 (50 °C), 55 (70 °C); SOL IN CARBON TETRACHLORIDE, PETROLEUM ETHER, NAPHTHA, XYLENE, DIBUTYL PHTHALATE, LIQUID PETROLATUM, ACETONE, ALCOHOL, VEGETABLE OILS; VERY SOL IN WATER-MISCIBLE ORGANIC SOLVENTS;FREELY SOL IN GLYCERIN;Water Solubility = 71000 mg/L @ 25 °C
Appearance	Solid
Storage	4°C, sealed storage, away from moisture and light*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)
Complexity	546
Covalently-Bonded Unit Count	2
Defined Atom Stereocenter Count	0
EC Number	209-406-4
Exact Mass	444.21576897
Heavy Atom Count	29
Hydrogen Bond Acceptor Count	7
Hydrogen Bond Donor Count	0
Isomeric SMILES	CCCCC(CC)COC(=O)CC(C(=O)OCC(CC)CCCC)S(=O)(=O)[O-].[Na+]
LogP	4.89030
MDL Number	MFCD00012455
Monoisotopic Mass	444.21576897
Physical State	Solid
Rotatable Bond Count	8
Shipping	Can be shipped at room temperature, where not in use may vary.
Stability	Stable. Combustible. Incompatible with strong oxidizing agents.
Storage Conditions	2-8ºC
Topological Polar Surface Area	118 Ų
WGK Germany	2

Knowledge & Learning Case Study Q&A

Docusate Sodium as a Cleaning Agent for Forward Osmosis Membranes

Ibrar I, et al. Chemosphere, 2022, 308(2), 136237.

Sodium docusate, commonly used as a laxative and earwax remover, has been innovatively applied as a chemical cleaning agent for forward osmosis (FO) membranes fouled by landfill leachate wastewater.
Flux Recovery: Remarkable flux recovery of nearly 100% was achieved using sodium docusate at a low concentration of 0.1% for 30 minutes, demonstrating its efficacy in cleaning fouled FO membranes.
Static Cleaning Efficiency: Sodium docusate proved effective in both dynamic (pumped) and static (non-pumped) cleaning modes, with static cleaning showing similar results to dynamic cleaning. This reduces the need for additional pumping energy, offering significant energy savings, especially for larger membrane areas.
Membrane Compatibility: The cleaning process with sodium docusate was carried out at neutral pH, which is compatible with most membrane materials. Importantly, the membrane's selectivity was not compromised during the cleaning process.
Environmental and Economic Benefits: Sodium docusate is more environmentally friendly compared to traditional acid or alkaline cleaning agents. Additionally, the cleaning solution can be reused for multiple cycles, reducing waste and costs.
Membrane Surface Analysis: Post-cleaning analysis using Scanning Electron Microscopy (SEM) confirmed the successful removal of fouling layers. Infrared Spectroscopy indicated a minimal residue of sodium docusate on the membrane surface, while contact angle measurements showed improved surface wettability after cleaning.
Conclusion: Sodium docusate offers a promising, efficient, and environmentally friendly solution for cleaning forward osmosis membranes fouled by landfill leachate. Its effectiveness in both dynamic and static cleaning modes, combined with its low environmental impact and potential for reuse, makes it a valuable option for membrane cleaning in wastewater treatment systems.

Sodium Docusate in Dimethyl Sulfoxide-Water Mixtures

Markarian SA, et al. Journal of Molecular Liquids, 2023, 369, 120960.

Sodium docusate, also known as dioctyl sulfosuccinate sodium (AOT), is widely recognized for its applications in pharmacy, biology, and medicine. This study explores the physicochemical behavior of AOT in mixed dimethyl sulfoxide (DMSO)-water solutions.
Critical Micelle Concentration (CMC): The study determined that the CMC of AOT increases with the rising mole fraction of DMSO in the DMSO-water mixture. This indicates that higher DMSO content requires a greater concentration of AOT to form micelles.
Thermodynamic Parameters: Negative Gibbs free energy of micellization was observed across all tested temperatures (298.15 to 318.15 K), indicating that micellization is thermodynamically favorable in these mixtures. However, as the DMSO concentration increases, significant changes in the micellization process are noted, particularly at DMSO mole fractions greater than 0.3.
Structural Changes and Micelle Formation: At higher DMSO contents, larger micellar agglomerates and multilamellar AOT vesicles were observed. The formation of DMSO self-associates contributes to these abrupt changes in the structural and phase behavior of AOT in the solution.
Conclusion: Sodium docusate exhibits complex micellization behavior in DMSO-water mixtures, with higher DMSO content leading to larger micelles and multilamellar vesicles. The findings of this study provide insights into the design of AOT-based systems in medical applications, where the control of micelle size and formation is crucial. The ability to manipulate micellization through DMSO concentration could lead to optimized delivery systems in pharmaceutical contexts.

What is the molecular formula of Docusate Sodium?

The molecular formula of Docusate Sodium is C20H37NaO7S.

What are some synonyms for Docusate Sodium?

Some synonyms for Docusate Sodium are Dioctyl sodium sulfosuccinate, Aerosol OT, and Dioctyl sulfosuccinate sodium salt.

What is the molecular weight of Docusate Sodium?

The molecular weight of Docusate Sodium is 444.6 g/mol.

What is the IUPAC name of Docusate Sodium?

The IUPAC name of Docusate Sodium is sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate.

What is the InChI code for Docusate Sodium?

The InChI code for Docusate Sodium is InChI=1S/C20H38O7S.Na/c1-5-9-11-16(7-3)14-26-19(21)13-18(28(23,24)25)20(22)27-15-17(8-4)12-10-6-2;/h16-18H,5-15H2,1-4H3,(H,23,24,25);/q;+1/p-1

What is the InChIKey for Docusate Sodium?

The InChIKey for Docusate Sodium is APSBXTVYXVQYAB-UHFFFAOYSA-M.

What is the Canonical SMILES of Docusate Sodium?

The Canonical SMILES of Docusate Sodium is CCCCC(CC)COC(=O)CC(C(=O)OCC(CC)CCCC)S(=O)(=O)[O-].[Na+].

What is the hydrogen bond donor count of Docusate Sodium?

The hydrogen bond donor count of Docusate Sodium is 0.

What is the hydrogen bond acceptor count of Docusate Sodium?

The hydrogen bond acceptor count of Docusate Sodium is 7.

How many rotatable bonds does Docusate Sodium have?

Docusate Sodium has 18 rotatable bonds.

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