| 词条 | Chelidonic acid |
| 释义 |
| Name = | ImageFile = Chelidonic acid Structural Formula V.1.svg | ImageSize = 200px | SystematicName = 4-Oxo-4H-pyran-2,6-dicarboxylic acid | OtherNames = Jerva acid; Jervaic acid; Jervasic acid; γ-Pyrone-2,6-dicarboxylic acid | IUPACName = | Section1 = {{Chembox Identifiers | CASNo = 99-32-1 | CASNo_Ref = {{cascite|correct|}} | PubChem = 7431 | ChemSpiderID = 7153 | SMILES = O=C\\1/C=C(\\O/C(C(=O)O)=C/1)C(=O)O | InChI = 1/C7H4O6/c8-3-1-4(6(9)10)13-5(2-3)7(11)12/h1-2H,(H,9,10)(H,11,12) | InChIKey = PBAYDYUZOSNJGU-UHFFFAOYAH | StdInChI = 1S/C7H4O6/c8-3-1-4(6(9)10)13-5(2-3)7(11)12/h1-2H,(H,9,10)(H,11,12) | StdInChIKey = PBAYDYUZOSNJGU-UHFFFAOYSA-N | Section2 = {{Chembox Properties | C=7 | H=4 | O=6 | Appearance = | Density = | MeltingPtC = 257 | MeltingPt_notes = (decomposes) | MeltingPt_ref = [1] | BoilingPt = | Solubility = | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | Section4 = {{Chembox Related | OtherCompounds = Meconic acid }} | Section5 = | Section6 = }} Chelidonic acid is a heterocyclic organic acid with a pyran skeleton. PreparationChelidonic acid can be prepared in two steps from diethyl oxalate and acetone:[1][2] {{clear left}} UsesChelidonic acid is used to synthesize 4-pyrone via thermal decarboxylation.[3] Natural occurrenceChelidonic acid was first discovered in extracts of Chelidonium majus.[4][5][6] It occurs naturally in plants of the Asparagales order.[7] Potassium chelidonate has been found to be responsible for nyctinasty in some plants; specifically, it has been found to regulate the closing of leaves of Cassia mimosoides at nightfall.[8][9] See also
References1. ^1 {{OrgSynth | author=E. Raymond Riegel and F. Zwilgmeyer | year=1937 |title=Chelidonic acid |volume=17 |pages=40 |collvol=2 |collvolpages=126 |prep=CV2P0126}} 2. ^{{cite journal |author1=G. Horvath |author2=C. Russa |author3=Z. Koentoes |author4=J. Gerencser | journal = Synth. Comm. | year = 1999 | volume = 29 | issue = 21 | pages = 3719–3732 | doi = 10.1080/00397919908086011 | title = A new Efficient Method for the Preparation of 2,6-Pyridinedihiethyl Ditosylates from Dimethyl 2,60-Pyridinedicarboxylates}} 3. ^{{cite book|last1=Weygand|first1=Conrad|editor1-last=Hilgetag|editor1-first=G.|editor2-last=Martini|editor2-first=A.|title=Weygand/Hilgetag Preparative Organic Chemistry|date=1972|publisher=John Wiley & Sons, Inc.|location=New York|isbn=0471937495|page=1009|edition=4th}} 4. ^{{cite book|last1=Roscoe|first1=H.E.|last2=Schorlemmer|first2=C.|title=A Treatise on Chemistry, Volume 3, Part 2|date=1890|publisher=D Appleton and Company|location=New York|pages=624|edition=1st|url=https://books.google.com/books?id=xM4cAQAAIAAJ&pg=PA624#v=onepage&q&f=false}} 5. ^Probst, Joseph M. A. (1839) [https://babel.hathitrust.org/cgi/pt?id=uiug.30112025845162;view=1up;seq=127 "Beschreibung und Darstellungsweise einiger bei der Analyse des Chelidonium majus aufgefundenen Stoffe"] (Description and methods of preparation of some substances found during the analysis of Chelidonium majus), Annalen der Chemie und Pharmacie, 29 (2) : 113–131 ; see especially pp. 116–118. 6. ^See also: Lerch, Joseph Udo (1846) [https://babel.hathitrust.org/cgi/pt?id=hvd.hx3bgw;view=1up;seq=291 "Untersuchung der Chelidonsäure"] (Investigation of chelidonic acid), Annalen der Chemie und Pharmacie, 57 : 273–318. 7. ^{{cite web|url=http://www.mobot.org/MOBOT/research/APweb/orders/asparagalesweb.htm#Asparagales|website=Angiosperm Phylogeny Website|title=Asparagales|publisher=Angiosperm Phylogeny Group|accessdate=30 August 2017}} 8. ^{{cite journal | doi = 10.1016/S0031-9422(98)00134-4| title = Leaf-opening substance of a nyctinastic plant, Cassia mimosoides| journal = Phytochemistry| volume = 49| issue = 3| pages = 633| year = 1998| last1 = Ueda| first1 = Minoru| last2 = Ohnuki| first2 = Takashi| last3 = Yamamura| first3 = Shosuke}} 9. ^{{cite journal | last1 = Ueda| first1 = Minoru| last2 = Yamamura| first2 = Shosuke| date = 1998 | url = https://books.google.com/books?id=aI_3BDcYKXgC&pg=PA437#v=onepage&q&f=false | title = Chemical studies on plant movement | journal = Current Organic Chemistry | volume = 2 | issue = 4 | pages = 437–461}} 2 : 4-Pyrones|Dicarboxylic acids |
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