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Chemistry

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Also known as: 27176-87-0, 2-dodecylbenzenesulfonic acid, Dodecylbenzenesulphonic acid, Dodecyl benzene sulfonic acid, O-dodecylbenzenesulfonic acid, Benzenesulfonic acid, 2-dodecyl-
Molecular Formula
C18H30O3S
Molecular Weight
326.5  g/mol
InChI Key
WBIQQQGBSDOWNP-UHFFFAOYSA-N
FDA UNII
QMO4A07H35

27176-87-0
1 2D Structure

27176-87-0

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-dodecylbenzenesulfonic acid
2.1.2 InChI
InChI=1S/C18H30O3S/c1-2-3-4-5-6-7-8-9-10-11-14-17-15-12-13-16-18(17)22(19,20)21/h12-13,15-16H,2-11,14H2,1H3,(H,19,20,21)
2.1.3 InChI Key
WBIQQQGBSDOWNP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCCCCCCCCCC1=CC=CC=C1S(=O)(=O)O
2.2 Other Identifiers
2.2.1 UNII
QMO4A07H35
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Deterlon

2. Dobanic Acid 83

3. Dodecyl Benzene Sulfonic Acid Sodium

4. Dodecylbenzenesulfonic Acid, Potassium Salt

5. Dodecylbenzenesulfonic Acid, Sodium Salt

6. Sodium Dodecyl Benzene Sulfonate

7. Sodium Dodecylbenzenesulfonate

8. Sodium Laurylbenzenesulfonate

9. Sulfanol

10. Sulfanol Np 1

11. Sulfonol

2.3.2 Depositor-Supplied Synonyms

1. 27176-87-0

2. 2-dodecylbenzenesulfonic Acid

3. Dodecylbenzenesulphonic Acid

4. Dodecyl Benzene Sulfonic Acid

5. O-dodecylbenzenesulfonic Acid

6. Benzenesulfonic Acid, 2-dodecyl-

7. Dodecylbenzene Sulfonic Acid

8. 47221-31-8

9. 2-dodecylbenzene-1-sulfonic Acid

10. Qmo4a07h35

11. 1323-12-2

12. Unii-qmo4a07h35

13. Schembl24533

14. 2-dodecylbenzenesulphonic Acid

15. Dodecyl Benzene Sulphonic Acid

16. Dtxsid10860152

17. 2-dodecylbenzene-1-sulphonic Acid

18. Chebi:149774

19. 2-dodecylbenzenesulfonicacid

20. Zinc2014249

21. Akos015893068

22. As-76054

23. Cs-0256295

24. Ft-0698141

25. Q27287337

26. 111839-63-5

27. 124743-21-1

28. 147625-74-9

29. 27157-97-7

30. 39355-45-8

31. 54824-36-1

32. 889890-18-0

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 326.5 g/mol
Molecular Formula C18H30O3S
XLogP36.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count12
Exact Mass326.19156599 g/mol
Monoisotopic Mass326.19156599 g/mol
Topological Polar Surface Area62.8 Ų
Heavy Atom Count22
Formal Charge0
Complexity359
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Surface-Active Agents

Agents that modify interfacial tension of water; usually substances that have one lipophilic and one hydrophilic group in the molecule; includes soaps, detergents, emulsifiers, dispersing and wetting agents, and several groups of antiseptics. (See all compounds classified as Surface-Active Agents.)


Disinfectants

Substances used on inanimate objects that destroy harmful microorganisms or inhibit their activity. Disinfectants are classed as complete, destroying SPORES as well as vegetative forms of microorganisms, or incomplete, destroying only vegetative forms of the organisms. They are distinguished from ANTISEPTICS, which are local anti-infective agents used on humans and other animals. (From Hawley's Condensed Chemical Dictionary, 11th ed) (See all compounds classified as Disinfectants.)


4.2 Absorption, Distribution and Excretion

Linear alkylbenzenesulfonic acid is absorbed through the gills and body surface of fish (carp), distributed via blood to the various tissues and organs, transported to the hepatopancreas (liver for goldfish and others), and subsequently, via bile, eliminated with the feces. /Linear alkylbenzenesulfonic acid/

Kikuchi M et al; Exotoxicol Environ Safety 2 (2): 115-27 (1978) as cited in ITC/USEPA; Information Review #236 (Draft) Mono(C10-16) Alkylbenzenesulfonic Acids and Their Sodium Salts p.56 (1981)


(14)C-labeled sodium dodecylbenzenesufonate (DBS) ... administered daily in the diet at a concn of 1.4 mg/kg to male rats for 5 weeks. ... From a total uptake of 1.213 + or - 0.08 mg/animal of DBS, 81.8% was excreted during the dosing period; 52.4% in feces and 29.4% in urine. Low levels of (14)C-DBS-derived residues were detected in all tissues analyzed on day 35 of the /study/. Following 1 week on normal diet only 7.8% of the nominally stored amount of (14)C was found in the excreta. Single ip injection of 0.385 mg (14)C-DBS/rat 2.26 + or - 0.15 mg/kg body weight resulted in total elimination of 94.5% within 10 days. 84.7% of the dose was eliminated the first 24 hr. All (14)C-DBS fecal and renal metabolites were ... highly polar. /Sodium dodecylbenzenesulfonate/

PMID:6623504 Lay JP et al; Toxicol Lett 17 (1-2): 187-92 (1983)


After single oral dose of /(35)S-labeled/ sodium dodecylbenzenesulfonate, rats excreted 64% and 24% of the dose in urine and feces, respectively. A similar study of repeated doses of /(14)C-labeled/ alkylbenzenesulfonate (mean molecular wt 349, a major constituent of detergents) to rhesus monkeys has shown that radioactivity did not accumulate in the tissues. /Aromatic, sulfur-containing cmpd/

The Royal Society of Chemistry. Foreign Compound Metabolism in Mammals. Volume 6: A Review of the Literature Published during 1978 and 1979. London: The Royal Society of Chemistry, 1981., p. 354


The bioconcentration factor for (14)C alkylbenzene in bluegill sunfish (L. machrochirus) was 35. The value was significantly smaller than the predicted bioconcentration factor of 6300; the discrepancy was ascribed to metabolism. Alkylbenzene had similar patterns of tissue distribution and depuration rates when compared to its sulfonated counterpart, linear alkylbenzene sulfonate, a surfactant in laundry detergents, which had been shown to be readily metabolized.

Werner AF, Kimerle RA; Environ Toxicol Chem 1 (2): 143 (1982)


(14)C labelled sodium dodecylbenzene sulfonate was administered daily in the diet at a concentration of 1.4 mg/kg to male rats for 5 weeks. From the total uptake (1.213 +/- 0.08 mg/animal) of sodium dodecylbenzene sulfonate, 81.8% was excreted during the dosing period; 52.4% in feces and 29.4% in urine. Low levels of (14)C sodium dodecylbenzene sulfonate derived residues were detected in all tissues analyzed on day 35 of the experiment. Following 1 week on normal diet only 7.8% of the nominally stored amount of (14)C was found in the excreta. Single ip application of 0.385 mg (14)C sodium dodecylbenzene/rat (2.26 +/- 0.15 mg/kg body weight) resulted in a total elimination of 94.5% within 10 days. 84.7% of the dose was eliminated in the first 24 hours. All fecal and renal (14)C sodium dodecylbenzene derived activity consisted of highly polar metabolites.

PMID:6623504 Lay JP et al; Toxicol Lett 17 (1-2): 187 (1983)


4.3 Mechanism of Action

/A study was conducted/ to investigate the action mechanism of sulfonate anionic surfactant against plant viral infection, inhibitory action of sodium and calcium salts of branched dodecylbenzenesulfonic acid to tobacco mosaic virus (TMN) ordinary strain ... using the French bean local lesion assay method. The results suggest that the inhibitory action of dodecylbenzenesulfonic acid to TMV infection is not due to disintegration or inactivation of TMV but due to the depression of viral replication resulting from the disturbance in metabolism of the host cell and the function of the membrane at an early stage of TMV infection in that cell. /Sodium and calcium salts of dodecylbenzenesulfonic acid/

Watanabe T el al: J Pest Sci 5 (4): 503-9 (1980)


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