Malvin

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For other uses, see Malvin (disambiguation).

Malvin

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^Y
PubChem	441765
	ChEBI	CHEBI:75030^N
Jmol-3D images	{{#if:COC1=CC(=CC(=C1O)OC)C2=C(C=C3C(=CC(=CC3=[O+]2)O)OC4 C(C(C(C(O4)CO)O)O)O)OC5C(C (C(C(O5)CO)O)O)O\|Image 1
SMILES COC1=CC(=CC(=C1O)OC)C2=C(C=C3C(=CC(=CC3=[O+]2)O)OC4 C(C(C(C(O4)CO)O)O)O)OC5C(C (C(C(O5)CO)O)O)O
Properties
Molecular 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]
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Malvin is a naturally occurring chemical of the Anthocyanin family. It is a diglucoside of malvidin mainly found as a pigment in herbs like Malva (Malva sylvestris), Primula and Rhododendron.^[2] 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 but not limited to the following:^{[citation needed]}

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^[3]), 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.^{[citation needed]}

References

↑ 1.0 1.1 MSDS from CarlRoth (German)
↑ J. A. Joule, K. Mills: Heterocyclic Chemistry., S. 173, Blackwell Publishing, 2000, ISBN 978-0-632-05453-4
↑ 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 Malvidin Peonidin Petunidin Pulchellidin Rosinidin

Anthocyanins	Antirrhinin (Cyanidin-3-O-rutinoside) Callistephin (Pelargonidin 3-O-glucoside) Chrysanthemin (Cyanidin-3-O-glucoside) Malvin (Malvidin 3,5-diglucoside) Myrtillin (Delphinidin-3-O-glucoside) Oenin (Malvidin-3-O-glucoside) Peonidin-3-O-glucoside Petunidin 3,5-O-diglucoside Petunidin 3-O-arabinoside Petunidin 3-O-galactoside Petunidin-3-O-glucoside Petunidin 3-O-rhamnoside Petunidin-3-O-rutinoside Primulin (Malvidin-3-O-galactoside) Pulchellidin 3-glucoside Pulchellidin 3-rhamnoside Tulipanin (Delphinidin 3-O-rutinoside)

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 Cyanidin-3-O-(di-p-coumarylglucoside)-5-glucoside Delphinidin-3-O-(6-p-coumaroyl)glucoside Malvidin-3-O-(6-p-coumaroyl)glucoside Petanin (petunidin 3-[6-O-(4-O-E-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-d-glucopyranoside]-5-O-β-d-glucopyranoside) 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 Gentiodelphin (delphinidin 3-O-glucosyl-5-O-(6-O-caffeoyl-glucosyl)-3′-O-(6-O-caffeoyl-glucoside))

p-hydroxybenzoylated anthocyanins	Violdelphin

Flavanol-anthocyanin adducts	Malvidin glucoside-ethyl-catechin

Misc.	Metalloanthocyanins (Commelinin Cyanosalvianin Protocyanin Protodelphin) Pyranoanthocyanins Copigmentation

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