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

KEGG |

* C08718 N

PubChem CID

* 441765

UNII |

* I9I120531L Y

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

Tracking categories (test):

* SizeSet

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. ↑ 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
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.

* v
* t
* e

Anthocyanidins and their anthocyanin glucosides

3-Hydroxyanthocyanidins|

* 5-Desoxy-peonidin
* Aurantinidin
* Cyanidin
* 6-Hydroxycyanidin
* Delphinidin
* Fisetinidin
* Guibourtinidin
* Pelargonidin
* Robinetinidin

3-Deoxyanthocyanidins|

* Apigeninidin
* Columnidin
* Diosmetinidin
* Gesneridin
* Luteolinidin
* Tricetinidin

O-Methylated anthocyanidins|

* 5-Desoxy-malvidin
* Capensinidin
* Europinidin
* Hirsutidin
* Kaempferidinidin
* Malvidin
* Peonidin
* Petunidin
* Pulchellidin
* Rosinidin

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)

Flavanol-anthocyanin adducts|

* Malvidin glucoside-ethyl-catechin
* Catechin(4α→8)pelargonidin 3-O-β-glucopyranoside
* Epicatechin(4α→8)pelargonidin 3-O-β-glucopyranoside
* Afzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
* Epiafzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside

Miscellaneous|

* Metalloanthocyanins (commelinin)
* Cyanosalvianin
* Protocyanin
* Protodelphin)
* Pyranoanthocyanins
* Copigmentation
* Anthocyanone A (degradation product of oenin)
* Malvone (oxidation product of malvin)

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