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Chemistry

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Also known as: 151-21-3, Sodium lauryl sulfate, Sodium dodecylsulfate, Sodium lauryl sulphate, Sodium dodecyl sulphate, Dodecyl sodium sulfate

Molecular Formula

C₁₂H₂₅NaO₄S

Molecular Weight

288.38 g/mol

InChI Key

DBMJMQXJHONAFJ-UHFFFAOYSA-M

FDA UNII

368GB5141J

An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.

1 2D Structure

Sodium Lauryl Sulfate API

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;dodecyl sulfate

2.1.2 InChI

InChI=1S/C12H26O4S.Na/c1-2-3-4-5-6-7-8-9-10-11-12-16-17(13,14)15;/h2-12H2,1H3,(H,13,14,15);/q;+1/p-1

2.1.3 InChI Key

DBMJMQXJHONAFJ-UHFFFAOYSA-M

2.1.4 Canonical SMILES

CCCCCCCCCCCCOS(=O)(=O)[O-].[Na+]

2.2 Other Identifiers

2.2.1 UNII

368GB5141J

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Dodecyl Sulfate, Sodium

2. Irium

3. Lauryl Sulfate, Sodium

4. Sodium Lauryl Sulfate

5. Sulfate, Sodium Dodecyl

6. Sulfate, Sodium Lauryl

2.3.2 Depositor-Supplied Synonyms

1. 151-21-3

2. Sodium Lauryl Sulfate

3. Sodium Dodecylsulfate

4. Sodium Lauryl Sulphate

5. Sodium Dodecyl Sulphate

6. Dodecyl Sodium Sulfate

7. Neutrazyme

8. Sodium N-dodecyl Sulfate

9. Irium

10. Sulfuric Acid Monododecyl Ester Sodium Salt

11. Dodecyl Sulfate Sodium Salt

12. Dodecyl Sulfate, Sodium Salt

13. Anticerumen

14. Duponal

15. Duponol

16. Gardinol

17. Sodium Monododecyl Sulfate

18. Dreft

19. Aquarex Methyl

20. Duponol Methyl

21. Solsol Needles

22. Stepanol Methyl

23. Duponol Waqa

24. Stepanol Wac

25. Stepanol Waq

26. Duponol Qx

27. Richonol Af

28. Perlandrol L

29. Perlankrol L

30. Sipex Sb

31. Sipex Sd

32. Standapol Wa-ac

33. Stepanol Me Dry

34. Duponol Me

35. Richonol A

36. Richonol C

37. Sintapon L

38. Duponol C

39. Maprofix Lk

40. Standapol Waq

41. Stepanol Me

42. Stepanol Wa

43. Akyposal Sds

44. Carsonol Sls

45. Maprobix Neu

46. Maprofix Neu

47. Maprofix Wac

48. Aquarex Me

49. Dupanol Waq

50. Duponol Qc

51. Duponol Wa

52. Duponol Wa Dry

53. Duponol Waq

54. Empicol Lpz

55. Hexamol Sls

56. Melanol Cl

57. Duponal Waqe

58. Duponol Waqe

59. Duponol Waqm

60. Lanette Wax-s

61. Sterling Wa Paste

62. Conco Sulfate Wa

63. Conco Sulfate Wn

64. Nikkol Sls

65. Orvus Wa Paste

66. Sipex Op

67. Sipex Sp

68. Sipex Ub

69. Sipon Ls

70. Sipon Pd

71. Sipon Wd

72. Detergent 66

73. Montopol La Paste

74. Sipon Lsb

75. Maprofix Wac-la

76. Sterling Waq-ch

77. Cycloryl 21

78. Cycloryl 31

79. Stepanol Wa Paste

80. Conco Sulfate Wag

81. Conco Sulfate Wan

82. Conco Sulfate Was

83. Quolac Ex-ub

84. Odoripon Al 95

85. Sodiumdodecylsulfate

86. Avirol 118 Conc

87. Cycloryl 580

88. Cycloryl 585n

89. Lauyl Sodium Sulfate

90. Maprofix 563

91. Sinnopon Ls 95

92. Stepanol T 28

93. Sodium Laurilsulfate

94. Steinapol Nls 90

95. Empicol Ls 30

96. Empicol Lx 28

97. Lauryl Sodium Sulfate

98. Melanol Cl 30

99. Nals

100. Rewopol Nls 30

101. Standapol Waq Special

102. Standapol Was 100

103. Sinnopon Ls 100

104. Stepanol Wa-100

105. Carsonol Sls Special

106. Standapol 112 Conc

107. Stepanol Me Dry Aw

108. Avirol 101

109. Emersal 6400

110. Monogen Y 100

111. Carsonol Sls Paste B

112. Sodium;dodecyl Sulfate

113. Stepanol Methyl Dry Aw

114. Berol 452

115. Emal 10

116. Emal O

117. Sipon Ls 100

118. N-dodecyl Sulfate Sodium

119. Sodium Monolauryl Sulfate

120. Monododecyl Sodium Sulfate

121. Sodiumlauryl Ether Sulfate

122. Lauryl Sulfate Sodium Salt

123. Conco Sulfate Wa-1200

124. Conco Sulfate Wa-1245

125. Dehydag Sulfate Gl Emulsion

126. Product No. 75

127. Product No. 161

128. Mfcd00036175

129. Emulsifier No. 104

130. Texapon K 12 P

131. Chebi:8984

132. P And G Emulsifier 104

133. Sodium Lauryl Sulfate Ether

134. Sls

135. Sodium Laurylsulfate

136. Nsc-402488

137. Texapon K 1296

138. Nci-c50191

139. Laurylsulfuric Acid Sodium Salt

140. Natriumalkyl(c8-c20)-sulfate

141. Dodecyl Alcohol, Hydrogen Sulfate, Sodium Salt

142. Dodecylsulfuric Acid Sodium Salt

143. Sodium Lauryl Sulfate, Synthetic

144. Finasol Osr2

145. Incronol Sls

146. Natriumlaurylsulfat

147. 368gb5141j

148. Ncgc00091020-03

149. E487

150. Jordanol Sl-300

151. Finasol Osr(sub 2)

152. Dodecyl Sulfate Sodium

153. Monagen Y 100

154. Perklankrol Esd 60

155. Caswell No. 779

156. Natrium Laurylsulfuricum

157. Dsstox_cid_6031

158. Dsstox_rid_77989

159. Dsstox_gsid_26031

160. 12738-53-3

161. 12765-21-8

162. 1334-67-4

163. Laurylsiran Sodny [czech]

164. Lauryl Sulfate, Sodium Salt

165. Dehydrag Sulfate Gl Emulsion

166. Dehydag Sulphate Gl Emulsion

167. Laurylsiran Sodny

168. Rhodapon Ub

169. Sodium Lauryl Sulfate 30%

170. Cas-151-21-3

171. Ccris 6272

172. Lauryl Sulfate Sodium

173. Hsdb 1315

174. Sodium Lauryl Sulfate, Dental Grade

175. Einecs 205-788-1

176. Epa Pesticide Chemical Code 079011

177. Nsc 402488

178. Cp 75424

179. Empicol

180. Ai3-00356

181. Unii-368gb5141j

182. Sodium Lauryl Sulfate [jan:nf]

183. Sodiumlauryl Sulfate

184. Sulfuric Acid Monododecyl Ester Sodium Salt (1:1)

185. Sodium Dodecylsulphate

186. Sodium Dedecyl Sulfate

187. Sodium-dodecyl-s-sds

188. Ipc-sds

189. Sodium N-dodecyl Sulphate

190. Sodium Lauryl Sulfate Nf

191. Sds (20% Solution)

192. Sodium Monododecyl Sulphate

193. Lauryl Sulphate Sodium Salt

194. Ec 205-788-1

195. Dodecyl Sulphate Sodium Salt

196. Schembl1102

197. Sodium Lauryl Sulfate, Sds

198. Sodium Dodecyl Sulfate (sds)

199. Chembl23393

200. Sodium Dodecyl Sulphate (sds)

201. Sodium Dodecyl Sulphate Solution

202. Dtxsid1026031

203. Dodecyl Sulfuric Acid Sodium Salt

204. Dodecyl Sulphuric Acid Sodium Salt

205. Sodium Lauryl Sulfate (jp17/nf)

206. Sodium Lauryl Sulfate [ii]

207. Sodium Lauryl Sulfate [mi]

208. Bcp30594

209. Cs-b1770

210. Sodium Lauryl Sulfate [fcc]

211. Sodium Lauryl Sulfate [jan]

212. Tox21_111059

213. Tox21_201614

214. Tox21_300149

215. Bdbm50530482

216. Sodium Laurilsulfate [mart.]

217. Sodium Lauryl Sulfate [hsdb]

218. Sodium Lauryl Sulfate [inci]

219. Sodium Lauryl Sulfate [vandf]

220. Akos015897278

221. Akos025147308

222. Tox21_111059_1

223. Db00815

224. Dodecyl Sulfuric Acid Ester Sodium Salt

225. Sodium Lauryl Sulfate [usp-rs]

226. Sodium Lauryl Sulfate [who-dd]

227. Ncgc00091020-01

228. Ncgc00091020-02

229. Ncgc00254225-01

230. Ncgc00259163-01

231. Ncgc00274082-01

232. As-14730

233. Sodium Laurilsulfate [ep Impurity]

234. Lauryl Sulfate, Sodium Salt (25% Aq.)

235. Sodium Laurilsulfate [ep Monograph]

236. D1403

237. Ft-0603358

238. Ft-0700721

239. I0352

240. S0588

241. D01045

242. F16341

243. S-4600

244. S-4601

245. Sodium Dodecyl Sulfate Biotech Grd 100g

246. Q422241

247. Sodium N-dodecyl Sulfate, 98%, For Electrophoresis

248. Sodium N-dodecyl Sulfate (sds), 20% Aqueous Solution

249. F0001-0539

250. Z1695728983

251. Sodium Dodecylsulfate;sodium Lauryl Sulphate;dodecyl Sodium Sulfate

252. Dodecyl Sodium Sulfate, Dodecyl Sulfate Sodium Salt, Lauryl Sulfate Sodium Salt, Sds, Sodium Lauryl Sulfate

2.4 Create Date

2005-09-08

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₂₅NaO₄S
Molecular Weight	288.38 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	12
Exact Mass	288.13712473 g/mol
Monoisotopic Mass	288.13712473 g/mol
Topological Polar Surface Area	74.8 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	249
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Therapeutic Uses

/VET/ foot & mouth disease virus is highly resistant to.../sodium lauryl sulfate/, yet TGE virus is sensitive... fungistatic (incl Candida & Trichophyton spp) & concn of 2% & over eliminated drug resistance & sex transfer factors in E coli. Inhibits growth of many G-pos bacteria...ineffective against G-neg types.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 542

/VET/ Sodium lauryl sulfate is used as a flea and tick repellant in one registered pesticide product--a flea and tick shampoo for cats and dogs. Sodium lauryl sulfate also is a widely used component of many nonpesticidal consumer products currently marketed in the United States, including shampoos and fruit juices.

USEPA/Office of Prevention, Pesticides and Toxic Substances; Registration Eligibility Decision Document - Lauryl Sulfate Salts p. 3 EPA-73B-F-93-Q09 (September 1993) Available from, as of June 16, 2014: https://www.epa.gov/pesticides/reregistration/status.htm

/VET/ as wetting agent for some antibiotics & antimicrobials (tylosin, sulfaquinoxaline, tyrothricin, etc) for oral & topical use. Widely used in ointment bases & as wetting agent for some insecticides & anthelmintics. Also useful in producing clear gel shampoos.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 542

/EXPL THER/ About 1/3 of HIV positive mothers transmit the virus to their newborns, and 1/2 of these infections occur during breastfeeding. Sodium dodecyl sulfate (SDS), an anionic surfactant, is a common ingredient of cosmetic and personal care products. SDS is "readily biodegradable" with low toxicity and "is of no concern with respect to human health". Up to 1 g of SDS/kg is the maximum safe dose for children. Alkyl sulfates, including SDS, are microbicidal against HIV types 1 and 2, herpes simplex virus type 2 (HSV-2), human papillomaviruses and chlamydia. /The study/ hypothesizes that SDS treatment of milk will inactivate HIV-1 without significant harm to its nutritional value and protective functions and may define a treatment of choice for breastwas at 37 degrees C for 10 min. SDS-PAGE and Lowry were used to analyze protein content. Antibody content and function was studied by rocket immunoelectrophoresis (RIE), immunoturbodimentric (ITM) quantitation and ELISA. The creamatocrit was also analyzed. HIV-1 infectivity was measured by MAGI assay. SDS removal was by Detergent-OutN (Geno Technology, Inc.). SDS quantitation is by methylene blue-chloroform method. Inactivation of HIV-1 with SDS occurs at or above 0.025%. In milk samples, 1% and 0.1% SDS reduced HSV-2 infectivity. At least 90% of SDS can be efficiently removed with Detergent-OutN, with protein recovery of 80%-100%. Gross protein species are conserved as indicated by PAGE analyses. Fat and energy content of SDS-treated breast milk remains unchanged. 0.1% SDS can be removed from human milk without altering the creamatocrit. ELISA of serum IgG (rubella) proved it remains functional in the presence of SDS and after its removal. sIgA, IgG and IgM in breast milk are conserved after SDS-treatment when measured by RIE and ITM. CONCLUSIONS: SDS (0.025%) can inactivate HIV-1 in vitro and HSV-2 in breast milk. SDS can be efficiently removed from milk samples. SDS treatment of milk does not significantly alter protein content. Antibody function in serum and levels in breast milk are maintained after treatment and removal of SDS. 0.1% SDS does not alter fat concentration in milk and energy content is conserved. SDS or related compounds may be used to prevent breast milk transmission of HIV-1.

Stoltzfus SU et al;Pediatr 49 (4 Pt 2 Suppl): 253A (2001)

/EXPL THER/ A broad-spectrum vaginal microbicide must be effective against a variety of sexually transmitted disease pathogens and be minimally toxic to the cell types found within the vaginal epithelium, including vaginal keratinocytes. /The study/ assessed the sensitivity of primary human vaginal keratinocytes to potential topical vaginal microbicides nonoxynol-9 (N-9), C31G, and sodium dodecyl sulfate (SDS). Direct immunofluorescence and fluorescence-activated cell sorting analyses demonstrated that primary vaginal keratinocytes expressed epithelial cell-specific keratin proteins. Experiments that compared vaginal keratinocyte sensitivity to each agent during a continuous, 48-hr exposure demonstrated that primary vaginal keratinocytes were almost five times more sensitive to N-9 than to either C31G or SDS. To evaluate the effect of multiple microbicide exposures on cell viability, primary vaginal keratinocytes were exposed to N-9, C31G, or SDS three times during a 78-hr period. In these experiments, cells were considerably more sensitive to C31G than to N-9 or SDS at lower concentrations within the range tested. When agent concentrations were chosen to result in an endpoint of 25% viability after three daily exposures, each exposure decreased cell viability at the same constant rate. When time-dependent sensitivity during a continuous 48-hr exposure was examined, exposure to C31G for 18 hr resulted in losses in cell viability not caused by either N-9 or SDS until at least 24 to 48 hr. Cumulatively, these results reveal important variations in time- and concentration-dependent sensitivity to N-9, C31G, or SDS within populations of primary human vaginal keratinocytes cultured in vitro. These investigations represent initial steps toward both in vitro modeling of the vaginal microenvironment and studies of factors that impact the in vivo efficacy of vaginal topical microbicides.

PMID:10858360 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC89991 Krebs FC et al; Antimicrob Agents Chemother. 44(7): 1954-60 (2000)

4.2 Minimum/Potential Fatal Human Dose

3. 3= Moderately toxic: probable oral lethal dose (human) 0.5-5 g/kg, between 1 oz & 1 pint (or 1 lb) for 70 kg person (150 lb). /Alkyl sodium sulfates/

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-274

4.3 Drug Indication

SLS is used as a surfactant in shampoos and toothpastes. SLS also has microbicidal activities against both enveloped (Herpes simplex viruses, HIV-1, Semliki Forest virus) and nonenveloped (papillomaviruses, reovirus, rotavirus and poliovirus) viruses, although it has not been approved for this use.

5 Pharmacology and Biochemistry

5.1 Pharmacology

SLS is an anionic surfactant. Its amphiphilic properties make it an ideal detergent.

5.2 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.)

5.3 Mechanism of Action

Like other surfactants, SLS is amphiphilic. It thus migrates to the surface of liquids, where its alignment and aggregation with other SLS molecules lowers the surface tension. This allows for easier spreading and mixing of the liquid. SLS has potent protein denaturing activity and inhibits the infectivity of viruses by by solubilizing the viral envelope and/or by denaturing envelope and/or capsid proteins.

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Pharm-RX Chemical

U.S.A

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Cosmoprof India

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Cosmoprof India

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Spectropharma

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Pet Inc

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Cosmoprof India

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Sodium Lauryl Sulfate API

About the Company : Pharm-Rx has earned an outstanding reputation since its establishment in 1991, serving as a reputable importer and distributor of active ingredients to the pharmaceutical, nutritio...

Pharm-Rx has earned an outstanding reputation since its establishment in 1991, serving as a reputable importer and distributor of active ingredients to the pharmaceutical, nutritional supplement, and food industries. The company maintains an exceptionally selective approach to its suppliers, personally visiting manufacturers overseas to ensure the highest standards. The sustained growth of Pharm-Rx can be attributed to its steadfast commitment to three core values: quality ingredients, competitive pricing, and unparalleled customer service.

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