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| | ImageFile = malvin.svg | | ImageFile = malvin.svg | ||
| | ImageSize = 250px | | ImageSize = 250px | ||
| | IUPACName = 3,5-Bis(β-<small>D</small>-glucopyranosyloxy)- |
| 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{oxy}-1λ<sup>4</sup>-benzopyran-1-ylium | | SystematicName = 7-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3,5-bis{oxy}-1λ<sup>4</sup>-benzopyran-1-ylium | ||
| | OtherNames = Malvidin 3,5-diglucoside | | OtherNames = Malvidin 3,5-diglucoside | ||
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| }} | }} | ||
| |Section2={{Chembox Properties | |Section2={{Chembox Properties | ||
| | Formula = |
| 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 = |
| MolarMass = {{bulleted list | ||
| |655.578 mg/L (cation) | |||
| |691.031 mg/L (chloride)}} | |||
| | Appearance = Reddish blue, odorless powder<ref name=carlroth></ref> | | Appearance = Reddish blue, odorless powder<ref name=carlroth></ref> | ||
| | Density = | | Density = | ||
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| == Natural occurrences == | == Natural occurrences == | ||
| 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-( |
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> | ||
| 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. | 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. | ||
Latest revision as of 04:45, 29 January 2024
For other uses, see Malvin (disambiguation).
| |
| Names | |
|---|---|
| IUPAC name 3,5-Bis(β-D-glucopyranosyloxy)-4′,7-dihydroxy-3′,5′-dimethoxyflavylium | |
| Systematic IUPAC name 7-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3,5-bis{oxy}-1λ-benzopyran-1-ylium | |
| Other names Malvidin 3,5-diglucoside | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.037.063 
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| KEGG | |
| PubChem CID | |
| UNII | |
| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
| Chemical formula |
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| Molar mass |
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| Appearance | Reddish blue, odorless powder |
| Solubility in water | Nearly insoluble |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 N verify (what is ?)
Infobox references
| |
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
- ^ MSDS from CarlRoth (German)
- 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
- 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
- J. A. Joule, K. Mills: Heterocyclic Chemistry., S. 173, Blackwell Publishing, 2000, ISBN 978-0-632-05453-4
- 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
- Chang, S; Tan, C; Frankel, EN; Barrett, DM (2000). "Low-density lipoprotein antioxidant activity of phenolic compounds and polyphenol oxidase activity in selected clingstone peach cultivars". Journal of Agricultural and Food Chemistry. 48 (2): 147–51. doi:10.1021/jf9904564. PMID 10691607.