| Revision as of 11:53, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 400846505 of page Periplanone_B for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 13:32, 6 May 2023 edit LegionMammal978 (talk | contribs)Extended confirmed users7,894 edits add semisystematic name |
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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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{{Chembox |
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{{Chembox |
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| verifiedrevid = 400845224 |
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| verifiedrevid = 464199257 |
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| ImageFile = Periplanone B.png |
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| ImageFile = Periplanone B.png |
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| ImageFile2 = Periplanone B ball-and-stick.png |
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| ImageSize = 200px |
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| ImageSize = 200px |
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| IUPACName = (1''S'', 2''S'',5''S'',10''S'')-(6''E'')-8-Methylidene-5-propan-2-ylspiroundec-6-ene-2,2'-oxirane]-3-one |
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| IUPACName = (5''E'')-1β,2β:10,14-Diepoxygermacra-4(15),5-dien-9-one |
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| SystematicName = (1''R'',2''R'',5''S'',6''E'',10''R'')-8-Methylidene-5-(propan-2-yl)-11-oxaspiroundecane-2,2′-oxiran]-6-en-3-one |
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| OtherNames = (1''Z'',5''E'')-1,10(14)-Diepoxy-4(15),5-germacradiene-9-one |
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| OtherNames = (1''Z'',5''E'')-1,10(14)-Diepoxy-4(15),5-germacradiene-9-one |
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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|correct|chemspider}} |
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| ChemSpiderID = 9065530 |
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| ChemSpiderID = 9065530 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = KVFSFBCTIZBPRK-KGDVWTLMSA-N |
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| StdInChIKey = KVFSFBCTIZBPRK-KGDVWTLMSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 61228-92-0 --> |
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| CASNo = 61228-92-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 8HV41M9E86 |
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| PubChem = 10890266 |
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| PubChem = 10890266 |
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| SMILES = O=C21(OC1)3O3CC(\C=C\(C(C)C)C2)=C |
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| SMILES = O=C21(OC1)3O3CC(\C=C\(C(C)C)C2)=C |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=15|H=20|O=3 |
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| C=15 | H=20 | O=3 |
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| BoilingPt = |
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| Solubility = }} |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = }} |
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'''Periplanone B''' is a ] produced by the female American cockroach,<ref>{{cite journal | author = Okada, K| title = Behavioral responses of male Periplaneta americana L. to female sex pheromone components, periplanone-A and periplanone-B | journal = Journal of Chemical Ecology | volume = 16 | issue = 9 | pages = 2605–2614 | date = September 1990 | doi = 10.1007/BF00988072 | pmid = 24264316 | s2cid = 30323914 |display-authors=etal}}</ref> '']''. It is a sexual attractant to male cockroaches, especially at short ranges.<ref>{{cite journal |author1=Chow, YF |author2=Wang, SF | title = Attraction responses of the American cockroach to synthetic periplanone-B | journal = Journal of Chemical Ecology | volume = 7 | issue = 2 | pages = 265–272 | year = 1981 | doi = 10.1007/BF00995749 |pmid=24420472 |s2cid=21794952 }}</ref> |
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== History == |
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The activity of this pheromone was first described in 1952, but it was not until 25 years later that Persoons ''et al.'' reported the gross structure of periplanones A and B. The ] configuration and first ] were reported by ]'s group at ] in 1979.<ref name="Nicolaou">{{cite book |title= Classics in Total Synthesis|last= Nicolaou|first= K. C.|author-link=K. C. Nicolaou |author2=E. J. Sorensen|year= 1996|publisher= VCH|location= Weinheim, Germany|isbn= 3-527-29284-5|page=|url=https://archive.org/details/classicstotalmet00kcni|url-access= limited}}</ref> |
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== References == |
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{{reflist}} |
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{{Ketone-stub}} |