| Revision as of 17:30, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 413644799 of page 2-Octyl_cyanoacrylate for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 01:15, 2 January 2025 edit Timothytomato (talk | contribs)15 edits capitalized iTag: Visual edit |
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{{Distinguish|Octyl cyanoacrylate}}{{Chembox |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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| Verifiedfields = changed |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 399299649 |
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| verifiedrevid = 477215083 |
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| ImageFile = 2-octyl cyanoacrylate.png |
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| ImageFile = 2-Octylcyanacrylat.svg |
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| ImageSize = 200px |
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| ImageAlt = |
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| ImageSize = 200px |
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| ImageAlt = |
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| IUPACName = Octan-2-yl 2-cyanoacrylate |
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| PIN = Octan-2-yl 2-cyanoprop-2-enoate |
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| OtherNames = 2-Octyl 2-cyanoacrylate; 1-Methylheptyl cyanoacrylate |
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| OtherNames = 2-Octyl 2-cyanoacrylate; 1-Methylheptyl cyanoacrylate |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 10632587 |
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| ChemSpiderID = 7991439 |
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| InChI = 1/C12H19NO2/c1-2-3-4-5-6-7-8-11(9-10-13)12(14)15/h9H,2-8H2,1H3,(H,14,15)/p-1/b11-9- |
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| InChI = 1/C12H19NO2/c1-4-5-6-7-8-11(3)15-12(14)10(2)9-13/h11H,2,4-8H2,1,3H3 |
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| InChIKey = IYPUCXCSXNMZHP-IJTYZBEIBF |
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| InChIKey = CQVWXNBVRLKXPE-UHFFFAOYAO |
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| SMILES1 = (=O)C(/CCCCCCCC)=C\C#N |
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| SMILES = C=C(C#N)C(OC(C)CCCCCC)=O |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C12H19NO2/c1-2-3-4-5-6-7-8-11(9-10-13)12(14)15/h9H,2-8H2,1H3,(H,14,15)/p-1/b11-9- |
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| StdInChI = 1S/C12H19NO2/c1-4-5-6-7-8-11(3)15-12(14)10(2)9-13/h11H,2,4-8H2,1,3H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = IYPUCXCSXNMZHP-LUAWRHEFSA-M |
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| StdInChIKey = CQVWXNBVRLKXPE-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|PubChem}} |
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| CASNo = <!-- blanked - oldvalue: 133978-15-1 --> |
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| PubChem = |
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| CASNo = 133978-15-1 |
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| PubChem = 9815689 |
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| SMILES = C=C(C#N)C(OC(C)CCCCCC)=O}} |
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| EC_number = 700-845-1 |
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| Section2 = {{Chembox Properties |
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| DrugBank = DB12040 |
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| C=12|H=19|N=1|O=2 |
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| DTXSID = DTXSID30888954 |
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| Appearance = |
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| Density = |
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| UNII = L23GHX71SK |
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| MeltingPt = |
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| Beilstein = 11343617 |
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}} |
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| BoilingPt = |
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|Section2={{Chembox Properties |
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| Solubility = }} |
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| C=12 | H=19 | N=1 | O=2 |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| Appearance = |
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| FlashPt = |
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| Density = |
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| Autoignition = }} |
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| MeltingPt = |
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| BoilingPt = |
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| Solubility = }} |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = }} |
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}} |
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}} |
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'''2-Octyl cyanoacrylate''' is a ] ] typically used as a ] adhesive (under the brand name Dermabond).<ref name=fda>{{cite web|url=http://www.accessdata.fda.gov/cdrh_docs/pdf/P960052b.pdf|title=Summary of Safety and Effectiveness Data|publisher=Food and Drug Administration|date=1998}}</ref> It is closely related to ]. The use of 2-octyl cyanoacrylate was approved in 1998; offered as an alternative to stitches, sutures, and or adhesive strips.<ref name=":0">{{Citation |last=Perera |first=AG Nuwan |title=2-Octyl Cyanoacrylate |date=2022 |url=http://www.ncbi.nlm.nih.gov/books/NBK532293/ |work=StatPearls |place=Treasure Island (FL) |publisher=StatPearls Publishing |pmid=30335326 |access-date=2022-08-19 |last2=Tavarez |first2=Melissa M.}}</ref> |
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== Adhesion mechanism == |
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When the 2-octyl cyanoacrylate monomers are exposed to anions, provided either by moisture from the skin or ] they quickly polymerize causing an ] binding to the most superficial layer of ]. The seal formed by the cyanoacrylate is water tight allowing for the wound to heal uninterrupted.<ref name=":0" /> |
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=== Anti-microbial properties === |
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Anti-microbial properties have been observed against ] and non-] ], but are not fully understood. It is believed that the interaction between the positively charged ] and the negatively charged 8-octyl cyanoacrylate destabilizes the ] of the bacteria, killing it. <ref name=":0" /> |
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== References == |
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{{reflist}} |
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==See also== |
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* ] |
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* ] |
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* ] |
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* ] |
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{{DEFAULTSORT:Octyl cyanoacrylate, 2-}} |
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] |
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] |
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] |