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{{otheruses|Malvin (disambiguation)}} |
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{{other uses|Malvin (disambiguation)}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 400998953 |
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|ImageFile=malvin.png |
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| verifiedrevid = 424866738 |
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|ImageSize=200px |
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| ImageFile = malvin.svg |
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|IUPACName= <small>(2S,3R,4S,5S,6R)-2-oxy]-3-chromenyliumyl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol</small>|OtherNames= |
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| ImageSize = 250px |
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|Section1= {{Chembox Identifiers |
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| IUPACName = 3,5-Bis(β-<small>D</small>-glucopyranosyloxy)-4{{prime}},7-dihydroxy-3{{prime}},5{{prime}}-dimethoxyflavylium |
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| CASNo=16727-30-3 |
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| SystematicName = 7-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3,5-bis{oxy}-1λ<sup>4</sup>-benzopyran-1-ylium |
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| PubChem=441765 |
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| OtherNames = Malvidin 3,5-diglucoside |
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| SMILES=COC1=CC(=CC(=C1O)OC)C2=C (C=C3C(=CC(=CC3=2)O)OC4 C(C(C(C(O4)CO)O)O)O)OC5C(C (C(C(O5)CO)O)O)O |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 16727-30-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = I9I120531L |
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| PubChem = 441765 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 75030 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = C08718 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 390365 |
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| ChemSpiderID_Comment = (cation) |
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| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID1 = 16498815 |
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| ChemSpiderID1_Comment = (chloride) |
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| SMILES = COC1=CC(=CC(=C1O)OC)C2=C(C=C3C(=CC(=CC3=2)O)O4((((O4)CO)O)O)O)O5((((O5)CO)O)O)O |
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| SMILES_Comment = (cation) |
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| SMILES1 = .O5(O)(O)(CO)O5Oc2cc(O)cc3c(c(O1O(CO)(O)(O)1O)cc23)c4cc(OC)c(O)c(OC)c4 |
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| SMILES1_Comment = (chloride) |
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| InChI = 1S/C29H34O17/c1-40-15-3-10(4-16(41-2)20(15)33)27-17(44-29-26(39)24(37)22(35)19(9-31)46-29)7-12-13(42-27)5-11(32)6-14(12)43-28-25(38)23(36)21(34)18(8-30)45-28/h3-7,18-19,21-26,28-31,34-39H,8-9H2,1-2H3,(H-,32,33)/p+1/t18-,19-,21-,22-,23+,24+,25-,26-,28-,29-/m1/s1 |
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| InChI_Comment = (cation) |
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| InChIKey = CILLXFBAACIQNS-BTXJZROQSA-O |
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| InChI1 = 1S/C29H34O17.ClH/c1-40-15-3-10(4-16(41-2)20(15)33)27-17(44-29-26(39)24(37)22(35)19(9-31)46-29)7-12-13(42-27)5-11(32)6-14(12)43-28-25(38)23(36)21(34)18(8-30)45-28;/h3-7,18-19,21-26,28-31,34-39H,8-9H2,1-2H3,(H-,32,33);1H/t18-,19-,21-,22-,23+,24+,25-,26-,28-,29-;/m1./s1 |
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| InChI1_Comment = (chloride) |
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| InChIKey1 = RHKJIVJBQJXLBY-FTIBDFQESA-N |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=• C<sub>29</sub>H<sub>35</sub>O<sub>17</sub><sup>+</sup> (cation) |
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| Formula = {{bulleted list |
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|C<sub>29</sub>H<sub>35</sub>O<sub>17</sub><sup>+</sup> (cation) |
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• C<sub>29</sub>H<sub>35</sub>O<sub>17</sub>Cl (chloride) |
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|C<sub>29</sub>H<sub>35</sub>O<sub>17</sub>Cl (chloride)}} |
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| MolarMass=• 655.578 (cation) |
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| MolarMass = {{bulleted list |
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|655.578 mg/L (cation) |
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• 691.031 (chloride) |
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|691.031 mg/L (chloride)}} |
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| ExactMass = 655.187425 |
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| Appearance=reddish blue, odourless powder <ref name=carlroth></ref> |
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| Appearance = Reddish blue, odorless powder<ref name=carlroth></ref> |
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| Solubility= nearly unsoluble <ref name=carlroth/> |
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| Solubility= Nearly insoluble<ref name=carlroth/> |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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'''Malvin''' is a naturally occurring ] of the ] family. |
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Malvin reacts in the presence of H<sub>2</sub>O<sub>2</sub> to form ].<ref>Oxidation of the anthocyanidin-3,5-diglucosides with H2O2: The structure of malvone. G. Hrazdina, Phytochemistry, July 1970, Volume 9, Issue 7, Pages 1647–1652, {{doi|10.1016/S0031-9422(00)85290-5}}</ref> The ortho-benzoyloxyphenylacetic acid esters reaction product is dependant of the pH: it is obtained under acidic conditions whereas under neutral conditions, the reaction product is the 3-O-acyl-glucosyl-5-O-glucosyl-7-hydroxy coumarin.<ref>Oxidation products of acylated anthocyanins under acidic and neutral conditions. Géza Hrazdina and Angeline J. Franzese, Phytochemistry, January 1974, Volume 13, Issue 1, Pages 231–234, {{doi|10.1016/S0031-9422(00)91300-1}}</ref> |
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'''Malvin''' is a naturally occurring ] of the ] family. It is a ] of ] mainly found as a ] in herbs like ] ('']''), ] and ].<ref>J. A. Joule, K. Mills: ''Heterocyclic Chemistry.'', S. 173, Blackwell Publishing, 2000, ISBN 9780632054534</ref> It can be found in a variety of common foods, including but not limited to the following:{{Citation needed|date=November 2007}} |
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== Natural occurrences == |
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*Vegetables: ], ], ], ], ], ], ], ] (green and black), ], ], ], ], ], ], ] |
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It is a ] of ] mainly found as a ] in herbs like ] ('']''), '']'' and '']''.<ref>J. A. Joule, K. Mills: ''Heterocyclic Chemistry.'', S. 173, Blackwell Publishing, 2000, {{ISBN|978-0-632-05453-4}}</ref> ''M. sylvestris'' also contains ] (malvidin 3-(6{{pprime}}-malonylglucoside)-5-glucoside).<ref>Malonated anthocyanins in malvaceae: Malonylmalvin from Malva sylvestris. Kosaku Takeda, Shigeki Enoki, Jeffrey B. Harborne and John Eagles, Phytochemistry, 1989, Volume 28, Issue 2, Pages 499–500, {{doi|10.1016/0031-9422(89)80040-8}}</ref> |
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*Nuts: ], ] |
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*Herbs/Spices: ], ], ] |
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*Fruit: ], ], ], ], ], ], ], ], ] (red and green), ], ], ], ], ], ], ], ], ] |
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*Fish: ] |
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*Dairy: ] (]), ], ], ] |
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*Sugar: ], ] |
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The characteristic floral ] of '']'' has been shown to be an example of ], a result of the presence of malvin and ] (a ] ]) in the ratio 1:9. |
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Malvin is not dangerous to ingest unless one develops an ] toward it. An allergy to malvin may result in ], severe ], ] or ] when foods containing it are ingested in large amounts.{{Citation needed|date=November 2007}} |
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=== Presence in food === |
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==References== |
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Malvin can be found in a variety of common foods, including ] (''Clingstone'' variety<ref name=Chang>{{cite journal | pmid = 10691607 | year = 2000 | last1 = Chang | first1 = S | last2 = Tan | first2 = C | last3 = Frankel | first3 = EN | last4 = Barrett | first4 = DM | title = Low-density lipoprotein antioxidant activity of phenolic compounds and polyphenol oxidase activity in selected clingstone peach cultivars | volume = 48 | issue = 2 | pages = 147–51 | journal = Journal of Agricultural and Food Chemistry | doi = 10.1021/jf9904564}}</ref>). |
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== References == |
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<references/> |
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<references/> |
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{{Anthocyanins}} |
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{{Anthocyanins}} |
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] |
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] |
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] |
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