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Malvidin

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Not to be confused withMalvidine.

Malvidin
Names

IUPAC name 3,4′,5,7-Tetrahydroxy-3′,5′-dimethoxyflavylium
Systematic IUPAC name 3,5,7-Trihydroxy-2-(4-hydroxy-3,5-dimethoxy)-1λ⁴-benzopyran-1-ylium
Identifiers
CAS Number	643-84-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:6674^N
ChEMBL	ChEMBL255753^Y ChEMBL592005^Y
ChemSpider	140095^Y
KEGG	C08716^Y
PubChem CID	159287
UNII	GL5KGZ4D8U^Y
CompTox Dashboard(EPA)	DTXSID30146622
InChI InChI=1S/C17H14O7/c1-22-14-3-8(4-15(23-2)16(14)21)17-12(20)7-10-11(19)5-9(18)6-13(10)24-17/h3-7H,1-2H3,(H3-,18,19,20,21)/p+1^Y Key: KZMACGJDUUWFCH-UHFFFAOYSA-O^Y InChI=1/C17H14O7/c1-22-14-3-8(4-15(23-2)16(14)21)17-12(20)7-10-11(19)5-9(18)6-13(10)24-17/h3-7H,1-2H3,(H3-,18,19,20,21)/p+1 Key: KZMACGJDUUWFCH-IKLDFBCSAG
SMILES Oc1cc2c(O)cc(O)cc2[o+]c1c3cc(OC)c(O)c(OC)c3
Properties
Chemical formula	C₁₇H₁₅O₇+
Molar mass	331.2968 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Malvidin is anO-methylated anthocyanidin, the 3',5'-methoxy derivative ofdelphinidin. As a primaryplant pigment, itsglycosides are highly abundant in nature.

Natural occurrences

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Malvidin is responsible for the blue color found in petals of thePrimula plants of thepolyanthus group. Blue flowers of the blue pimpernel (Anagallis monelli) have also a higher concentration of malvidin.

It is responsible primarily for the color of red wine,Vitis vinifera being one of its sources.^[1] It is also present in other berries, such as blueberries (Vaccinium corymbosum) or the saskatoon berries (Amelanchier alnifolia).^[2]^[3]

Chemistry

[edit]

Slightlyacidic andneutral solutions of malvidin are characteristically of a red color, whilebasic solutions of malvidin yield a blue color.

The breakdown of malvidin releasessyringic acid.

Use as a marker in archaeology

[edit]

The breakdown of malvidin releasessyringic acid as revealed in the examination of jars containingshedeh, a drink of Ancient Egypt. Malvidin is also present in the site of theAreni-1 winery, a 6,100-year-old winery discovered in 2007 in the Areni-1 cave complex in the village of Areni in the Vayots Dzor province ofArmenia.

Glycosides

[edit]

Malvin is a malvidin diglucoside.
Oenin is the malvidin-3-glucoside.
Primulin is the 3-O-galactoside of malvidin.
Malvidin 3-rutinoside is a pigment responsible for bract color inCurcuma alismatifolia (the Siam tulip).^[4]Acylated malvidin 3-rutinosides are responsible for the violet color ofPetunia integrifolia subsp. inflata.^[5]
Malvidin-3-O-glucoside-5-O-(6-acetylglucoside) is a pigment responsible for the blue color in 'Johnson's Blue' and other 'blue'geraniums^[6]

References

[edit]

^"Phytochemicals: Malvidin". Top Cultures. Archived from the original on April 1, 2010. Retrieved2009-05-20.
^Mazza G (2005)."Compositional and functional properties of saskatoon berry and blueberry".International Journal of Fruit Science.5 (3):99–118.doi:10.1300/J492v05n03_10.
^Bakowska-barczak; Marianchuk, M; Kolodziejczyk, P (2007). "Survey of bioactive components in Western Canadian berries".Canadian Journal of Physiology and Pharmacology.85 (11):1139–52.doi:10.1139/y07-102.PMID 18066116.
^Nakayama, M; Roh, MS; Uchida, K; Yamaguchi, Y; Takano, K; Koshioka, M (2000)."Malvidin 3-rutinoside as the pigment responsible for bract color in Curcuma alismatifolia".Bioscience, Biotechnology, and Biochemistry.64 (5):1093–5.doi:10.1271/bbb.64.1093.PMID 10879491.
^Tatsuzawa, F (1999). "Acylated malvidin 3-rutinosides in dusky violet flowers of Petunia integrifolia subsp. Inflata".Phytochemistry.52 (2):351–355.Bibcode:1999PChem..52..351T.doi:10.1016/S0031-9422(99)00095-3.
^Markham, Kenneth R.; Mitchell, Kevin A.; Boase, Murray R. (1997). "Malvidin-3-O-glucoside-5-O-(6-acetylglucoside) and its colour manifestation in 'Johnson's Blue' and other 'Blue' geraniums".Phytochemistry.45 (2):417–423.Bibcode:1997PChem..45..417M.doi:10.1016/S0031-9422(96)00831-X.

Anthocyanidins and their anthocyaninglucosides

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:

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- andtrans-)	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)