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ChemSpider 2D Image | 1,4-Bis(2-ethylhexyl) sulfosuccinate | C20H38O7S


1,4-Bis(2-ethylhexyl) sulfosuccinate

  • Molecular FormulaC20H38O7S
  • Average mass422.577 Da

1,4-Bis[(2-ethylhexyl)oxy]-1,4-dioxobutane-2-sulfonic acid

Docusate sodium.png

Docusate Sodium

Dioctyl sodium sulfosuccinate

  • Molecular FormulaC20H37NaO7S
  • Average mass444.558 Da
  • 216-684-0 [EINECS]
    577-11-7 [RN]

CAS Registry Number: 577-11-7 
CAS Name: Sulfobutanedioic acid 1,4-bis(2-ethylhexyl) ester sodium salt 
Additional Names: sulfosuccinic acid 1,4-bis(2-ethylhexyl) ester S-sodium salt; bis(2-ethylhexyl)sodium sulfosuccinate; dioctyl sodium sulfosuccinate; sodium dioctyl sulfosuccinate; DSS 
Trademarks: Aerosol OT (Cyanamid); Colace (Roberts); Comfolax (Searle); Coprola (Dunster); Dioctylal (Continental Pharma); Dioctyl (Medo); Diotilan (Chinoin); Disonate (Lannett); Doxinate (Hoechst); Doxol (Blair); Dulcivac (Harvey); Jamylène (Thžaplix); Molatoc; Molcer (Wallace); Nevax; Regutol (Schering-Plough); Soliwax (Concept Pharm.); Velmol (Berlex); Waxsol (Norgine); Yal (Ritter) 
Molecular Formula: C20H37NaO7S 
Molecular Weight: 444.56 
Percent Composition: C 54.03%, H 8.39%, Na 5.17%, O 25.19%, S 7.21% 
Literature References: Prepn: Jaeger, US2028091US2176423 (1936, 1939, both to Am. Cyanamid). Structure and wetting power: Caryl, Ind. Eng. Chem.33, 731 (1941). Comprehensive description: S. Ahuja, J. Cohen, Anal. Profiles Drug Subs.2, 199-219 (1973); 12, 713-720 (1983). For structure see Docusate calcium. 
Properties: Available as wax-like solid, usually in rolls of tissue-thin material; also as 50-75% solns in various solvents. Soly in water (g/l): 15 (25°), 23 (40°), 30 (50°), 55 (70°). Sol in CCl4, petr ether, naphtha, xylene, dibutyl phthalate, liq petrolatum, acetone, alcohol, vegetable oils. Very sol in water + alcohol, water + water-miscible organic solvents. Stable in acid and neutral solns; hydrolyzes in alkaline solns. 
Derivative Type: Docusate potassium 
CAS Registry Number: 7491-09-0 
Trademarks: Rectalad (Carter-Wallace) 
Molecular Formula: C20H37KO7S 
Molecular Weight: 460.67 
Percent Composition: C 52.14%, H 8.10%, K 8.49%, O 24.31%, S 6.96% 
NOTE: Ingredient of the laxative Peri-Colace (Roberts) which also contains casanthranol.Use: Sodium salt as pharmaceutic aid (surfactant); as wetting agent in industrial, pharmaceutical, cosmetic and food applications; dispersing and solubilizing agent in foods; adjuvant in tablet formation. 
Therap-Cat: Stool softener. 
Therap-Cat-Vet: Stool softener. 
Keywords: Laxative/Cathartic.

Docusate Calcium

Docusate Calcium 
CAS Registry Number: 128-49-4 
CAS Name: Sulfobutanedioic acid 1,4-bis(2-ethylhexyl)ester calcium salt 
Additional Names: bis[2-ethylhexyl]calcium sulfosuccinate; calcium dioctyl sulfosuccinate; dioctyl calcium sulfosuccinate 
Trademarks: Surfak (HMR) 
Molecular Formula: C40H74CaO14S2 
Molecular Weight: 883.22 
Percent Composition: C 54.40%, H 8.44%, Ca 4.54%, O 25.36%, S 7.26% 
Literature References: Prepd from dioctyl sodium sulfosuccinate dissolved in isopropanol and from calcium chloride dissolved in methanol: Klotz, US3035973 (1962 to Lloyd Brothers). 
Properties: White precipitate. Sol in mineral and vegetable oils, liq polyethylene glycol. Practically insol in glycerol. Claimed to have greater surface-active wetting properties than the sodium salt. 
NOTE: Ingredient of Doxidan (HMR) which also contains phenolphthalein. 
Therap-Cat: Stool softener. 
Keywords: Laxative/Cathartic.


free acid

  • Formula:C20H38O7S
  • MW:422.58 g/mol
  • CAS-RN:10041-19-7
  • EINECS:233-124-0

calcium salt

  • Formula:C40H74CaO14S2
  • MW:883.23 g/mol
  • CAS-RN:128-49-4
  • EINECS:204-889-8

potassium salt

  • Formula:C20H37KO7S
  • MW:460.67 g/mol
  • CAS-RN:7491-09-0
  • EINECS:231-308-5


CAS-RNFormulaChemical NameCAS Index Name
141-02-6C20H36O4bis(2-ethylhexyl) fumarate2-Butenedioic acid (E)-, bis(2-ethylhexyl) ester
C4H4O4(E)-2-butenedioic acid
104-76-7C8H18O2-ethyl-1-hexanol1-Hexanol, 2-ethyl- 


Image for - Thermophysical Properties of Trihexyltetradecyl Phosphonium Octylsulfosuccinate Ionic Liquid
Fig. 1:Synthesis of Trihexyltetradecylphosphonium octylsulfosuccinate [P6, 6, 6, 14][docusate]


Synthetic scheme for 1−6. 

Docusate is the common chemical and pharmaceutical name of the anionbis(2-ethylhexyl) sulfosuccinate, also commonly called dioctyl sulfosuccinate (DOSS).[2][3][4]

Salts of this anion, especially docusate sodium, are widely used in medicine as laxatives and as stool softeners, by mouth or rectally.[1] It is on the World Health Organization’s List of Essential Medicines.[5][6] Some studies claim that docusate is not more effective than a placebo for improving constipation.[7][8][9][10] Other docusate salts with medical use include those of calcium and potassium.[11][1][2]

Docusate salts are also used as food additivesemulsifiersdispersants, and wetting agents, among other uses.[12]


Sodium docusate was patented in 1937 by Coleman R. Caryl and Alphons O. Jaeger for American Cyanamid,[3] which commercialized it for many years as a detergent under the brand name Aerosol OT.

Its use for the treatment of constipation was first proposed in 1955 by James L. Wilson and David G. Dickinson,[4] and quicky popularized under the name Doxinate.[13]

Medical use


The main medical use of docusate sodium is to treat constipation, acting as a laxative and stool softener. In painful anorectal conditions such as hemorrhoid and anal fissures, it can help avoid pain caused by straining during bowel movements.

When administered by mouth, a bowel movement often occurs in 1 to 3 days,[1] while rectal use may be effective within 20 minutes.[14]

Sodium docusate is recommended as a stool softener for children.[1]

However, its effectiveness for constipation is poorly supported by evidence.[7][8] Multiple studies have found docusate to be no more effective than a placebo for improving constipation.[7][8][9][10] Others have found it to be less useful for the treatment of chronic constipation than psyllium.[10][15][16]

The medication may be given to people who are receiving opioid medication, although prolonged use may cause irritation of the gastrointestinal tract.[10][16]

Other medical uses

Docusate sodium, when used with ear syringing, may help with earwax removal, particularly in the case of impaction.[17]

Sodium docusate is also used as a lubricant in the production of tablets and as an emulsifier in topical preparations and other suspensions.[18]

Precautions and contraindications

Docusate sodium is approved and recommended as safe during pregnancy and breastfeeding.[19][20]

Docusate is not recommended in people with appendicitisacute abdomen, or ileus.[16]

When taken by mouth it should be ingested with plenty of water.

Side effects

Side effects are uncommon and typically mild,[1] and may include stomach pain, abdominal cramps or diarrhea,[1] Efficacy decreases with long-term use, and may cause poor bowel function.[11]

Serious allergic reactions may occur with the drug. The most severe side effect of docusate, although very rare, is rectal bleeding.[21]


Docusate might increase resorption of other drugs, for example, dantron (1,8-dihydroxyanthraquinone).[16]

Mechanism of action

Docusate sodium works by allowing more water to be absorbed by the stool.[11][22]

Docusate does not stay in the gastrointestinal tract, but is absorbed into the bloodstream and excreted via the gallbladder[16] after undergoing extensive metabolism.

The effect of docusate may not necessarily be all due to its surfactant properties. Perfusion studies suggest that docusate inhibits fluid absorption or stimulates secretion in the portion of the small intestine known as the jejunum.

Pharmaceutical brand names

In the U.S., docusate sodium for pharmaceutical use is available under multiple brand names: Aqualax, Calube, Colace, Colace Micro-Enema, Correctol Softgel Extra Gentle, DC-240, Dialose, Diocto, Dioctocal, Dioctosoftez, Dioctyn, Dionex, Doc-Q-Lace, Docu Soft, Docucal, Doculax, Docusoft S, DOK, DOS, Doss-Relief, DSS, Dulcolax – Stool Softener (not to be confused with another drug marketed under the Dulcolax brand, bisacodyl, which is a stimulant laxative), Ex-Lax Stool Softener, Fleet Sof-Lax, Genasoft, Kasof, Laxa-basic, Modane Soft, Octycine-100, Pedia-Lax, Preferred Plus Pharmacy Stool Softener, Regulax SS, Sulfalax Calcium, Sur-Q-Lax, Surfak Stool Softener, and Therevac-SB. Generic preparations are also available.

In the UK, dioctyl sodium sulfosuccinate is sold under the brand name Docusol (Typharm Ltd) and DulcoEase (Boehringer Ingelheim).

In Australia, dioctyl sodium sulfosuccinate is sold as Coloxyl and Coloxyl with senna.

In India, preparations include Laxatin by Alembic, Doslax by Raptakos Laboratories, Cellubril by AstraZeneca, and Laxicon by Stadmed.

Other uses

Dioctyl sodium sulfosuccinate is used as a surfactant in a wide range of applications, often under the name Aerosol-OT.[4][23] It is unusual in that it is able to form microemulsions without the use of co-surfactants, and it has a rich variety of aqueous-phase behavior including multiple liquid crystalline phases.[24]

Food additive

Dioctyl sodium sulfosuccinate has been approved by the US FDA as a “generally recognized as safe” (GRAS) additive.[25] It is used in a variety of food products, as a surface active agent, stabilizerthickenerwetting agent, processing aid, solubilizing agentemulsifier, and dispersant. The highest amount found in food products is 0.5% by weight, which include pasteurized cheese spreads, cream cheeses and salad dressings.[26] The FDA also approved its use as a wetting agent or solubilizer for flavoring agents in carbonated and non-carbonated drinks at levels up to 10 parts per million.[25]


Sodium docusate is the most widely used surfactant in reverse micelleencapsulation studies.[27]

Non-medical brand names

As a surfactant, docusate sodium is or has been commercialized under many brand names, including DSSj Aerosol OT, Alphasol OT, Colace, Complemix, Coprol, Dioctylal, Dioctyl-Medo Forte, Diotilan, Diovac, Disonate, Doxinate, Doxol, Dulsivac, Molatoc, Molofac, Nevax, Norval, Regutol, Softili, Solusol, Sulfimel DOS, Vatsol OT, Velmol, and Waxsol[28]


Structure and properties

The structural formula of the docusate anion is R−O−C(=O)−CH(SO−
2−C(=O)−O−R, where R is the 2-ethylhexyl groupH
2−. The conjugate acid can be described as the twofold carboxylate ester of sulfosuccinic acid with 2-ethylhexanol.

The compound is a white, wax-like, plastic solid, with an odor suggestive of octyl alcohol. It starts to decompose at about 220 °C.[28]

Solubility of dioctyl sodium sulfosuccinate in water is 14 g/L at 25 °C, increasing to 55 g/L at 70 °C.[28] Solubility is better in less polar solvents: 1:30 in ethanol, 1:1 in chloroform and diethylether, and practically unlimited in petroleum ether (25 °C). It also is highly soluble in glycerol, although this is a rather polar solvent. It is also highly soluble in xyleneoleic acidacetonediacetone alcoholmethanolisopropanol2-butanolmethyl acetateethyl acetatefurfurol, and vegetable oils.[28]

The ester groups are easily cleaved under basic conditions, but are stable against acids.[16]


Sodium dioctyl sulfosuccinate can be obtained by treating dioctyl maleate with sodium bisulfite. The bisulfite anion adds to the double bond:−CH=CH− + HSO−
3 → −CH(−SO−


Ingestion may cause the side effects described above, such as diarrhea, intestinal bloating, and occasionally cramping pains. Dioctyl sodium sulfosuccinate is not known to be carcinogenicmutagenic, or teratogenic.[29]

Marine species

Dioctyl sodium sulfosuccinate is of low toxicity for crustaceans such as the hermit crabClibanarius erythropus and the shrimp Crangon crangon. Toxicity for molluscs varies widely, with 48-hour LD50 found between 5 mg/l for the common limpet and 100 mg/l for the common periwinkle. Various species of phytoplankton have an LD50 around 8 mg/l.

In a 2010 study, dioctyl sodium sulfosuccinate exhibited higher toxicity against bacteria (Vibrio fischeriAnabaena sp.) and algae (Pseudokirchneriella subcapitata) than did a number of fluorinated surfactants (PFOSPFOA, or PFBS). Measuring bioluminescence inhibition of the bacteria and growth inhibition of the algae, the LD50 were in the range of 43–75 mg/l. Combinations of the fluorinated compounds with dioctyl sodium sulfosuccinate showed mid to highly synergistic effects in most settings, meaning that such combinations are significantly more toxic than the individual substances.[30]

Freshwater species

The substance is highly toxic for rainbow trout with a median lethal concentration (LC50) of 0.56 mg/l after 48 hours for the pure substance. It is only slightly to moderately toxic for rainbow trout fingerlings, and slightly toxic for harlequin rasboras (LC50 27 mg/l of a 60% formulation after 48 hours).


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  1. Jump up to:a b c d e f g h “Docusate Salts”. The American Society of Health-System Pharmacists. Archived from the original on 23 September 2015. Retrieved 11 August 2015.
  2. Jump up to:a b American Society of Health-System Pharmacists (15 August 2011). “Stool Softeners”Archived from the original on 5 September 2015.
  3. Jump up to:a b US 2181087, Caryl CR, Jaeger AO, “Detergent composition”, issued 21 November 1939, assigned to American Cyanamid
  4. Jump up to:a b c Wilson JL, Dickinson DG (May 1955). “Use of dioctyl sodium sulfosuccinate (aerosol O.T.) for severe constipation”. Journal of the American Medical Association158 (4): 261–3. doi:10.1001/jama.1955.02960040019006aPMID 14367076.
  5. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06.
  6. ^ “Docusate – Drug Usage Statistics”ClinCalc. Retrieved 18 February 2021.
  7. Jump up to:a b c Fakheri RJ, Volpicelli FM (February 2019). “Things We Do for No Reason: Prescribing Docusate for Constipation in Hospitalized Adults”Journal of Hospital Medicine14 (2): 110–113. doi:10.12788/jhm.3124PMID 30785419.
  8. Jump up to:a b c “Dioctyl Sulfosuccinate or Docusate (Calcium or Sodium) for the Prevention or Management of Constipation: A Review of the Clinical Effectiveness”CADTH Rapid Response Reports. 26 June 2014. PMID 25520993.
  9. Jump up to:a b Candy B, Jones L, Larkin PJ, Vickerstaff V, Tookman A, Stone P (May 2015). “Laxatives for the management of constipation in people receiving palliative care” (PDF). The Cochrane Database of Systematic Reviews13 (5): CD003448. doi:10.1002/14651858.CD003448.pub4PMC 6956627PMID 25967924.
  10. Jump up to:a b c d Ramkumar D, Rao SS (April 2005). “Efficacy and safety of traditional medical therapies for chronic constipation: systematic review”. The American Journal of Gastroenterology100 (4): 936–71. PMID 15784043.
  11. Jump up to:a b c 2013 Nurse’s Drug Handbook. Burlington, MA: Jones & Bartlett Learning. 2013. p. 366ISBN 9781449642846.
  12. ^ Ash M, Ash I (2004). Handbook of preservatives. Endicott, N.Y.: Synapse information resources. p. 375. ISBN 9781890595661.
  13. ^ Friedman M (October 1956). “Dioctyl sodium sulfosuccinate (doxinate) in chronic functional constipation”. American Practitioner and Digest of Treatment7 (10): 1588–91. PMID 13362832.
  14. ^ “Docusate sodium”. 18 December 2004. Archived from the original on 21 July 2011. Retrieved 6 March 2019.
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  16. Jump up to:a b c d e f Dinnendahl V, Fricke U, eds. (2010). Arzneistoff-Profile(in German). 2 (23 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.
  17. ^ “How effective is docusate as a cerumenolytic agent?” Archived from the original on 23 November 2010.
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  19. ^ Yaffe SJ (2011). Drugs in pregnancy and lactation : a reference guide to fetal and neonatal risk (9 ed.). Philadelphia: Wolters Kluwer Health/Lippincott Williams & Wilkins. p. 1651. ISBN 9781608317080.
  20. ^ Mahadevan U, Kane S (July 2006). “American gastroenterological association institute medical position statement on the use of gastrointestinal medications in pregnancy”. Gastroenterology131(1): 278–82. doi:10.1053/j.gastro.2006.04.048PMID 16831610.
  21. ^ Docusate Archived 16 July 2010 at the Wayback Machine
  22. ^ Hamilton RJ (2013). Tarascon pocket pharmacopoeia : 2013 classic shirt-pocket edition (27 ed.). Burlington, Ma.: Jones & Bartlett Learning. p. 112. ISBN 9781449665869.
  23. ^ Whiffen AJ (1946). “Aerosol OT in the preparation of microscopic mounts of fungi”. Mycologia38: 346. doi:10.1080/00275514.1946.12024063PMID 20983186.
  24. ^ Nave S, Eastoe J, Penfold J (November 2000). “What Is So Special about Aerosol-OT? 1. Aqueous Systems”. Langmuir16(23): 8733–8740. doi:10.1021/la000341q.
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  26. ^ “CFR – Code of Federal Regulations Title 21” Retrieved 29 January 2020.
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  29. ^ Docusate sodium Material Safety Data SheetArchived 2006-10-17 at the Wayback Machine
  30. ^ Rosal R, Rodea-Palomares I, Boltes K, Fernández-Piñas F, Leganés F, Petre A (September 2010). “Ecotoxicological assessment of surfactants in the aquatic environment: combined toxicity of docusate sodium with chlorinated pollutants”. Chemosphere81 (2): 288–93. Bibcode:2010Chmsp..81..288Rdoi:10.1016/j.chemosphere.2010.05.050PMID 20579683.

External links

Docusate sodium
Clinical data
Trade namesColace, Ex-Lax Stool Softener, others
Other namesDioctyl sulfosuccinate
License dataUSDailyMedDocusate
Routes of
By mouthrectal
Drug classStool softener
ATC codeA06AA02 (WHO)
Legal status
Legal statusUK:General sales list (GSL, OTC)US:OTCIn general: Over-the-counter (OTC)
Pharmacokinetic data
Onset of action12 hrs to 5 days[1]
Duration of action3 days[1]
showIUPAC name
CAS Number10041-19-7as salt: 577-11-7
PubChemCID11339as salt: 23673837
DrugBankDB11089as salt: DBSALT001500
ChemSpider10862as salt: 10861
UNIIM7P27195AGas salt: F05Q2T2JA0
KEGGas salt: D00305
ChEBICHEBI:534as salt: CHEBI:4674
ChEMBLChEMBL1477036as salt: ChEMBL1905872
E numberE480 (thickeners, …)
CompTox Dashboard (EPA)DTXSID8022959 
ECHA InfoCard100.008.553
Chemical and physical data
Molar mass421.57 g·mol−1
3D model (JSmol)Interactive imageas salt: Interactive image
Density1.1 g/cm3
Melting point153 to 157 °C (307 to 315 °F) 173-179 °C
Solubility in water1 in 70 parts mg/mL (20 °C)

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DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with AFRICURE PHARMA, ROW2TECH, NIPER-G, Department of Pharmaceuticals, Ministry of Chemicals and Fertilizers, Govt. of India as ADVISOR, earlier assignment was with GLENMARK LIFE SCIENCES LTD, as CONSUlTANT, Retired from GLENMARK in Jan2022 Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 32 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 32 PLUS year tenure till date Feb 2023, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 100 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 100 Lakh plus views on dozen plus blogs, 227 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 38 lakh plus views on New Drug Approvals Blog in 227 countries...... , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc He has total of 32 International and Indian awards

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