{{other uses|Malvin (disambiguation)}} {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424866738 | ImageFile = malvin.svg | ImageSize = 250px | IUPACName = 3,5-Bis(β-<small>D</small>-glucopyranosyloxy)-4{{prime}},7-dihydroxy-3{{prime}},5{{prime}}-dimethoxyflavylium | SystematicName = 7-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3,5-bis{[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ<sup>4</sup>-benzopyran-1-ylium | OtherNames = Malvidin 3,5-diglucoside |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 16727-30-3 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = I9I120531L | PubChem = 441765 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 75030 | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = C08718 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 390365 | ChemSpiderID_Comment = (cation) | ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID1 = 16498815 | ChemSpiderID1_Comment = (chloride) | SMILES = COC1=CC(=CC(=C1O)OC)C2=C(C=C3C(=CC(=CC3=[O+]2)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O | SMILES_Comment = (cation) | SMILES1 = [Cl-].O[C@@H]5[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]5Oc2cc(O)cc3[o+]c(c(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)cc23)c4cc(OC)c(O)c(OC)c4 | SMILES1_Comment = (chloride) | 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 | InChI_Comment = (cation) | InChIKey = CILLXFBAACIQNS-BTXJZROQSA-O | 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 | InChI1_Comment = (chloride) | InChIKey1 = RHKJIVJBQJXLBY-FTIBDFQESA-N }} |Section2={{Chembox Properties | Formula = {{bulleted list |C<sub>29</sub>H<sub>35</sub>O<sub>17</sub><sup>+</sup> (cation) |C<sub>29</sub>H<sub>35</sub>O<sub>17</sub>Cl (chloride)}} | MolarMass = {{bulleted list |655.578 mg/L (cation) |691.031 mg/L (chloride)}} | Appearance = Reddish blue, odorless powder<ref name=carlroth>[http://www.carl-roth.de/jsp/de-de/sdpdf/K013.PDF ''MSDS from CarlRoth'' (German)]</ref> | Density = | MeltingPt= | BoilingPt= | Solubility= Nearly insoluble<ref name=carlroth/> }} |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} }} '''Malvin''' is a naturally occurring chemical of the anthocyanin family.
Malvin reacts in the presence of H<sub>2</sub>O<sub>2</sub> to form malvone.<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>
== Natural occurrences == It is a diglucoside of malvidin mainly found as a pigment in herbs like Malva (''Malva sylvestris''), ''Primula'' and ''Rhododendron''.<ref>J. A. Joule, K. Mills: ''Heterocyclic Chemistry.'', S. 173, Blackwell Publishing, 2000, {{ISBN|978-0-632-05453-4}}</ref> ''M. sylvestris'' also contains malonylmalvin (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>
The characteristic floral jade coloration of ''Strongylodon macrobotrys'' has been shown to be an example of copigmentation, a result of the presence of malvin and saponarin (a flavone glucoside) in the ratio 1:9.
=== Presence in food === Malvin can be found in a variety of common foods, including peaches (''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>).
== References == <references/>
{{Anthocyanins}}
Category:O-methylated anthocyanins Category:Phenol ethers