| Revision as of 11:27, 13 April 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
Latest revision as of 17:48, 15 June 2023 edit undoZander12321 (talk | contribs)44 edits The wikipedia page incorrectly stated that an article showed micelle formation with a synergistic surfactant in water, and said that sarcosinate alone does not form micelles in water (which is incorrect). The article referenced was in a buffered water:ethanol mixture, and the paragraph has been updated accordingly. |
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{{Short description|Surfactant}} |
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{{Chembox |
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| Name = Sodium lauroyl sarcosinate |
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| Name = Sodium lauroyl sarcosinate |
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| ImageFile = Sodium lauroyl sarcosinate.svg |
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| ImageFile = Sodium lauroyl sarcosinate.svg |
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| ImageSize=250px |
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| ImageSize = 250px |
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| IUPACName =sodium acetate |
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| IUPACName = Sodium ''N''-(Dodecanoyl)-''N''-methylglycinate |
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| SystematicName = Sodium (''N''-methyldodecanamido)acetate |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 137-16-6 |
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| CASNo = 137-16-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 8716 |
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| SMILES = |
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| UNII = 632GS99618 |
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| PubChem = 23668817 |
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| InChI = 1S/C15H29NO3.Na/c1-3-4-5-6-7-8-9-10-11-12-14(17)16(2)13-15(18)19;/h3-13H2,1-2H3,(H,18,19);/q;+1/p-1 |
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| SMILES = CCCCCCCCCCCC(=O)N(C)CC(=O). |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=15|H=28|N=1|Na=1|O=3 |
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| C=15|H=28|N=1|Na=1|O=3 |
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| MeltingPtC = -1 |
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| MeltingPtC = 140 |
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| BoilingPtC = 100 |
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'''Sodium lauroyl sarcosinate''' (]), also known as '''sarkosyl''', is an ] derived from ], used as a foaming and cleansing agent in ], ] and foam wash products. |
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'''Sodium lauroyl sarcosinate''' (]), also known as '''sarcosyl''', is an ] derived from ] used as a foaming and cleansing agent in ], ], toothpaste, and foam wash products.<ref>{{cite journal|title = Some properties of N-acyl sarcosinate lipid vesicles | last=Wallach|first=D.F.H |author2=R. Mathur |author3=G.J.M. Redziniak |author4=J.F. Tranchant|journal=J. Soc.Cosmetic Chemists|year=1992|volume=43|pages=113–118}}</ref> |
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This surfactant is ] due to the ] 12-carbon chain (]) and the ] ]. Since the nitrogen atom is in an ] linkage, the nitrogen is not pH active and is neutrally charged in all aqueous solutions regardless of pH. The carboxylate has a ] of about 3.6 and is therefore negatively charged in solutions of pH greater than about 5.5. |
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In ] experiments, sarkosyl is used as an inhibitor of the initiation of ]<references/>. |
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]-sensitive ] can be prepared using this surfactant with another ]ic or water-insoluble ]s such as ].<ref>{{cite journal|title=Ternary phase behaviour and vesicle formation of a sodium N-lauroylsarcosinate hydrate/1-decanol/water system|last=Akter|first=N |author2=S. Radiman |author3=F. Mohamed |author4=I.A. Rahman |author5=M.I.H. Reza|journal=Scientific Reports|year=2011|volume=1|pages=71|doi=10.1038/srep00071 |pmid=22355590 |pmc=3216558|bibcode=2011NatSR...1E..71A}}</ref><ref>{{cite journal|last=Ambühl|first=M |author2=F. Bangerter |author3=P.L. Luisi |author4=P. Skrobal |author5=H.J. Watzke |journal=Langmuir |year=1993 |volume=9 |pages=36–38 |doi=10.1021/la00025a011 |title=Configurational changes accompanying vesiculation of mixed single-chain amphiphiles}}</ref><ref>{{cite journal |last=Ghosh |first=S |author2=J.Dey |journal=J. Colloid Interface Sci. |year=2011 |volume=358 |issue=1 |pages=208–216 |doi=10.1016/j.jcis.2011.02.054 |pmid=21420688 |title=Interaction of sodium N-lauroylsarcosinate with N-alkylpyridinium chloride surfactants: Spontaneous formation of pH-responsive, stable vesicles in aqueous mixtures|bibcode=2011JCIS..358..208G }}</ref> |
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Addition of an mixture of equal parts of sodium lauroyl sarcosinate and the non-ionic surfactant ] (S20) to a buffered water:ethanol solution led to the formation of micelle-like aggregates, even though neither surfactant formed micelles when present alone. Such aggregates can help carry other ], such as drugs, through the skin.<ref>{{cite journal| title = Synergistic effects of chemical enhancers on skin permeability: a case study of sodium lauroylsarcosinate and sorbitan monolaurate | last=Karande|first=P |author2=A.Jain |author3=A. Arora |author4=M.J.Ho |author5=S. Mitragotri |journal=Eur. J. Pharm. Sci.|year=2007|volume=31| issue=1|pages=1–7 |doi=10.1016/j.ejps.2007.01.004| pmid=17368869}}</ref> |
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==In culture== |
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Sodium lauroyl sarcosinate was sold as a special ingredient called "Gardol" in ] "Dental Cream", as ] was then called, during the 1950s<ref></ref><ref></ref><ref></ref> |
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through the mid-1960s in the US<ref></ref><ref></ref> |
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and the mid-1970s in France.<ref></ref> |
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Its current use as a preventive ] is in ] Baking Soda Toothpaste, a Church & Dwight product, where it is used as a ].<ref>{{cite web |url=https://churchdwight.com/ingredient-disclosure/dental-care/40002529-arm-hammer-toothpaste-dental-care.aspx |title=C&D Corporate - Ingredient Disclosure |author=<!--Not stated--> |date= |website=churchdwight.com |publisher=Church & Dwight Co., Inc. |access-date=November 24, 2021 |quote=}}</ref> |
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==References== |
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{{Reflist}} |
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==External links== |
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* Zemtsov, Alexander MD, MSC; Fett, Deborah MD, ''Dermatitis'', June 2005, Volume 16, Issue 2, p. 97 |
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{{organic-compound-stub}} |
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