| Revision as of 18:16, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 439885038 of page 4-Hydroxycoumarins for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 12:08, 14 January 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,043 edits Added s2cid. |
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{{about|the chemical compound|the class of drugs derived from it|4-Hydroxycoumarins}} |
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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 = 413272253 |
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| verifiedrevid = 477222305 |
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| Name = 4-Hydroxycoumarin |
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| ImageFile = 4-Hydroxycoumarin.PNG |
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| ImageFile = 4-Hydroxycoumarin.PNG |
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| ImageName = Chemical structure of 4-hydroxycoumarin |
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| ImageSize = 200px |
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| PIN = 4-Hydroxy-2''H''-1-benzopyran-2-one |
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| ImageName = Chemical structure of |
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| OtherNames = 4-Coumarinol<br>Benzotetronic acid |
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| IUPACName = 2-hydroxychromen-4-one |
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|Section1={{Chembox Identifiers |
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| OtherNames = 4-Coumarinol<br>Benzotetronic acid<br>4-hydroxycoumarin |
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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 = 10254753 |
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| ChemSpiderID = 10254753 |
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| InChIKey = PTNLHDGQWUGONS-OWOJBTEDBL |
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| InChIKey = PTNLHDGQWUGONS-OWOJBTEDBL |
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| SMILES1 = O/C2=C/C(=O)Oc1ccccc12 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 301141 |
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| ChEMBL = 301141 |
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| CASNo = 1076-38-6 |
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| CASNo = 1076-38-6 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 14101 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = X954ZLL2RD |
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| PubChem = 54682930 |
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| SMILES = Oc1ccc(/C=C/CO)cc1 |
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| SMILES = Oc1ccc(/C=C/CO)cc1 |
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| InChI = 1/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+ |
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| InChI = 1/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+ |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=9|H=6|O=3 |
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| Formula = C<sub>9</sub>H<sub>6</sub>O<sub>3</sub> |
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| Appearance = |
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| MolarMass = 162.14 g/mol |
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| Density = |
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| ExactMass = 162.031694 u |
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'''4-Hydroxycoumarin''' is a ] with a ] at the 4-position. |
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==Occurrence== |
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4-Hydroxycoumarin is an important fungal metabolite from the precursor coumarin, and its production leads to further fermentative production of the natural ] ]. This happens in the presence of naturally occurring ], which allows attachment of a second 4-hydroxycoumarin molecule through the linking carbon of the formaldehyde, to the 3-position of the first 4-hydroxycoumarin molecule, to give the semi-dimer the motif of the drug class. Dicoumarol appears as a fermentation product in spoiled ] silages and is considered a ].<ref>{{cite journal | author = Bye, A. | author2 = King, H. K. | date = 1970 | title = The biosynthesis of 4-hydroxycoumarin and dicoumarol by Aspergillus fumigatus Fresenius | journal = Biochemical Journal | volume = 117 | issue = 2 | pages = 237–245| pmid = 4192639 | pmc = 1178855 | doi=10.1042/bj1170237}}</ref> |
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4-Hydroxycoumarin is ] from ] and ] by the enzyme ].<ref>{{cite journal | title = A novel 4-hydroxycoumarin biosynthetic pathway |author = Liu, B. |author2 = Raeth, T. |author3 = Beuerle, T. |author4 = Beerhues, L. |name-list-style = amp |journal = Plant Mol. Biol. |year = 2010 |volume = 72 |issue = 1–2 |pages = 17–25 |pmid = 19757094 |doi=10.1007/s11103-009-9548-0|s2cid = 24313989 }}</ref> |
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==Anticoagulants== |
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After the identification of dicoumarol and its anticoagulant activity, it became the prototype for a class of drugs. 4-Hydroxycoumarin forms the core of the chemical structure of anticoagulants known collectively as ]. They include, for example, ], a pharmaceutical drug used to prevent formation of blood clots, and ], a widely used ]. |
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==See also== |
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*] |
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*] |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Hydroxycoumarin, 4-}} |
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] |