Malvin

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title: "Malvin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["o-methylated-anthocyanins", "phenol-ethers"] topic_path: "general/o-methylated-anthocyanins" source: "https://en.wikipedia.org/wiki/Malvin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424866738 | ImageFile = malvin.svg | ImageSize = 250px | IUPACName = 3,5-Bis(β-D-glucopyranosyloxy)-4,7-dihydroxy-3,5-dimethoxyflavylium | SystematicName = 7-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3,5-bis{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ4-benzopyran-1-ylium | OtherNames = Malvidin 3,5-diglucoside |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo = 16727-30-3 | UNII_Ref = | UNII = I9I120531L | PubChem = 441765 | ChEBI_Ref = | ChEBI = 75030 | KEGG_Ref = | KEGG = C08718 | ChemSpiderID_Ref = | ChemSpiderID = 390365 | ChemSpiderID_Comment = (cation) | ChemSpiderID1_Ref = | ChemSpiderID1 = 16498815 | ChemSpiderID1_Comment = (chloride) | SMILES = COC1=CC(=CC(=C1O)OC)C2=C(C=C3C(=CC(=CC3=[O+]2)O)O[C@H]4C@@HO)O[C@H]5C@@HO | SMILES_Comment = (cation) | SMILES1 = [Cl-].O[C@@H]5C@@HC@HC@@HO[C@H]5Oc2cc(O)cc3[o+]c(c(O[C@@H]1OC@HC@@HC@H[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 |C29H35O17+ (cation) |C29H35O17Cl (chloride)}} | MolarMass = {{bulleted list |655.578 mg/L (cation) |691.031 mg/L (chloride)}} | Appearance = Reddish blue, odorless powder | Density = | MeltingPt= | BoilingPt= | Solubility= Nearly insoluble |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = Malvin is a naturally occurring chemical of the anthocyanin family.

Malvin reacts in the presence of H2O2 to form malvone. 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.

Natural occurrences

It is a diglucoside of malvidin mainly found as a pigment in herbs like Malva (Malva sylvestris), Primula and Rhododendron. M. sylvestris also contains malonylmalvin (malvidin 3-(6-malonylglucoside)-5-glucoside).

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).

References

References

  1. [http://www.carl-roth.de/jsp/de-de/sdpdf/K013.PDF ''MSDS from CarlRoth'' (German)]
  2. 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
  3. 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
  4. J. A. Joule, K. Mills: ''Heterocyclic Chemistry.'', S. 173, Blackwell Publishing, 2000, {{ISBN. 978-0-632-05453-4
  5. 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
  6. (2000). "Low-density lipoprotein antioxidant activity of phenolic compounds and polyphenol oxidase activity in selected clingstone peach cultivars". Journal of Agricultural and Food Chemistry.

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