Malvin

Malvin
Names
	IUPAC name (S,3R,4S,5S,6R)-2-[[7-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-3chromenyliumyl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
	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)	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/(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).
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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:

Vegetables: avocado, beet, black-eyed pea, cabbage, carrot, eggplant, green pea, maize, olive (green and black), onion, pimento, potato, radish, tomato, turnip
Nuts: cashew, walnut
Herbs/Spices: paprika, mustard seed, cinnamon
Fruit: apple, fig, watermelon, rhubarb, strawberry, quince, peach (Clingstone variety[6]), pear, plum, grape (red and green), apricot, banana, blackberry, blueberry, boysenberry, cherry, cranberry, black currant
Fish: crabmeat
Dairy: albumin (cow's milk), cheese, yogurt, butter
Sugar: sugar beet, honey

Malvin is not dangerous to ingest unless one develops an allergy toward it. An allergy to malvin may result in constipation, severe gas, vomiting or diarrhea when foods containing it are ingested in large amounts.

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.

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[carlroth-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.