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^Y
3D model (JSmol)	(cation): Interactive image (chloride): Interactive image
ChEBI	CHEBI:75030^N
ChemSpider	390365 (cation)^N 16498815 (chloride)^N
ECHA InfoCard	100.037.063
KEGG	C08718^N
PubChem CID	441765
UNII	I9I120531L^Y
CompTox Dashboard (EPA)	DTXSID80895052
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^[1]
Solubility in water	Nearly insoluble^[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

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

^ ^a ^b 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.

Anthocyanidins and their anthocyanin glucosides

3-Hydroxyanthocyanidins

3-Deoxyanthocyanidins

O-Methylated anthocyanidins

Anthocyanins
(anthocyaninidin glycosides)

Glucosides:

Callistephin (Pelargonidin 3-O-glucoside)
Chrysanthemin (Cyanidin 3-O-glucoside)
Myrtillin (Delphinidin 3-O-glucoside)
Oenin (Malvidin 3-O-glucoside)
Peonidin 3-O-glucoside
Petunidin 3-O-glucoside
Pulchellidin 3-glucoside

Diglucosides:

Cyanin (Cyanidin 3,5-O-diglucoside)
Delphin (Delphinidin 3,5-O-diglucoside)
Malvin (Malvidin 3,5-diglucoside)
Pelargonin (Pelargonidin 3,5-O-diglucoside)
Peonin (Peonidin 3,5-O-diglucoside)
Petunin (Petunidin 3,5-O-diglucoside)

Others glycosides:

Antirrhinin (Cyanidin 3-O-rutinoside)
Ideain (Cyanidin 3-O-galactoside)
Delphinidin 3-O-rhamnoside
Petunidin 3-O-arabinoside
Petunidin 3-O-galactoside
Petunidin 3-O-rhamnoside
Petunidin 3-O-rutinoside
Primulin (Malvidin 3-O-galactoside)
Pulchellidin 3-rhamnoside
Tulipanin (Delphinidin 3-O-rutinoside)

Acylated anthocyanins

Acetylated anthocyanins	Cyanidin 3-O-(6-acetyl)glucoside Delphinidin 3-O-(6-acetyl)glucoside Malvidin 3-O-(6-acetyl)glucoside Petunidin 3-O-(6-acetyl)galactoside Petunidin 3-O-(6-acetyl)glucoside Peonidin 3-O-(6-acetyl)glucoside
Coumaroylated anthocyanins (cis- and trans-)	Cyanidin 3-O-(6-p-coumaroyl)glucoside Delphinidin 3-O-(6-p-coumaroyl)glucoside Malvidin 3-O-(6-p-coumaroyl)glucoside Petunidin 3-O-(6-p-coumaroyl)glucoside Peonidin 3-O-(6-p-coumaroyl)glucoside
Caffeoylated anthocyanins	Malvidin 3-O-(6-p-caffeoyl)glucoside Peonidin 3-O-(6-p-caffeoyl)glucoside
Malonylated anthocyanins	Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)
Acylated anthocyanin diglycosides	Cyanidin 3-O-(di-p-coumarylglucoside)-5-glucoside Gentiodelphin (delphinidin 3-''O''-glucosyl-5-''O''-(6-''O''-caffeoyl-glucosyl)-3′-''O''-(6-''O''-caffeoyl-glucoside)) Nasunin (Delphinidin 3-(p-coumaroylrutinoside)-5-glucoside) Petanin (petunidin 3-[6-O-(4-O-(E)-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-D-glucopyranoside]-5-O-β-D-glucopyranoside) Violdelphin (Delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-β-D-glucosyl)oxybenzoyl)-β-D-glucoside)