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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{oxy}-1λ-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)
ECHA InfoCard	100.037.063
KEGG	C08718
PubChem CID	441765
UNII	I9I120531L
CompTox Dashboard (EPA)	DTXSID201341471 DTXSID80895052, DTXSID201341471
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/s1Key: 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./s1Key: RHKJIVJBQJXLBY-FTIBDFQESA-N
SMILES (cation): COC1=CC(=CC(=C1O)OC)C2=C(C=C3C(=CC(=CC3=2)O)O4((((O4)CO)O)O)O)O5((((O5)CO)O)O)O (chloride): .O5(O)(O)(CO)O5Oc2cc(O)cc3c(c(O1O(CO)(O)(O)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 , 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

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
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.

• O-methylated anthocyanins
• Phenol ethers