Malvin

Malvin
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{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ4-benzopyran-1-ylium
	Other names Malvidin 3,5-diglucoside
Identifiers
CAS Number	16727-30-3 ;
3D model (JSmol)	(cation): Interactive image; (chloride): Interactive image;
ChEBI	CHEBI:75030 ;
ChemSpider	390365 (cation) ; 16498815 (chloride) ;
KEGG	C08718 ;
PubChem CID	441765;
UNII	I9I120531L ;
	InChI (cation): 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 Key: CILLXFBAACIQNS-BTXJZROQSA-O; (chloride): InChI=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 Key: RHKJIVJBQJXLBY-FTIBDFQESA-N;
	SMILES (cation): 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; (chloride): [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;
Properties
Chemical formula	C29H35O17+ (cation); C29H35O17Cl (chloride);
Molar mass	655.578 mg/L (cation); 691.031 mg/L (chloride);
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 [77 °F], 100 kPa).
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	Infobox references

Malvin is a naturally occurring chemical of the anthocyanin family.

Malvin reacts in the presence of H₂O₂ to form malvone.^[2] 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.^[3]

Natural occurrences

It is a diglucoside of malvidin mainly found as a pigment in herbs like Malva (Malva sylvestris), Primula and Rhododendron.^[4] M. sylvestris also contains malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside).^[5]

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^[6]).

References

↑ ^1.0 ^1.1 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.

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[carlroth-1] 1.0 ^1.1 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

[Chang-6] 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.