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The pyranoanthocyanins are a type of pyranoflavonoids. They are chemical compounds formed in
red wine Red wine is a type of wine made from dark-colored grape varieties. The color of the wine can range from intense violet, typical of young wines, through to brick red for mature wines and brown for older red wines. The juice from most purple gra ...
s by
yeast Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are estimated to consti ...
during fermentation processes or during controlled oxygenation processes during the
aging of wine The aging of wine is potentially able to improve the quality of wine. This distinguishes wine from most other consumable goods. While wine is perishable and capable of deteriorating, complex chemical reactions involving a wine's sugars, acids an ...
. The different classes of pyranoanthocyanins are carboxypyranoanthocyanins, methylpyranoanthocyanins, pyranoanthocyanin-flavanols, pyranoanthocyanin-phenols, portisins,
oxovitisin Oxovitisins are a type of pyranoanthocyanin with a pyranone ( 2-pyrone) component found in aged Port wines. They do not contain an oxonium ion component ( flavylium cation), as anthocyanins do. Therefore, they do not have an absorption maximum at ...
s and pyranoanthocyanin dimers; their general structure includes an additional ring (formed between the OH group at C-5 and the C-4 of the anthocyanin pyranic ring) that may have different substituents linked directly at C-10.


Examples

* Carboxypyranoanthocyanidins, can be considered markers of
microoxygenation Micro-oxygenation is a process used in winemaking to introduce oxygen into wine in a controlled manner. Developed in 1991 by Patrick DuCournau, working with the exceptionally tannic grape Tannat in Madiran, the process gained usage in modern winema ...
techniques * Hydroxyphenyl-pyranoanthocyanins * Vitisin A and B * Pinotins *
Portosins Portosins are vinyl pyranoanthocyanins, a type of blueish phenolic pigments, found in aged port wine. See also * Wine color The color of wine is one of the most easily recognizable characteristics of wines. Color is also an element in wine t ...
(vinylpyranoanthocyanins)


Vitisin A type

* Cyanidin-3-O-glucoside-pyruvic acid (m/z of +H ion:517, λmax 506 nm) * Cyanidin-3-O-acetylglucoside-pyruvic acid (559 - 507) * Cyanidin-coumaroylglucoside-pyruvic acid (661 - 507 nm) * Delphinidin-3-O-glucoside-pyruvic acid (533 - 507 nm) * Delphinidin-3-O-acetylglucoside-pyruvic acid (575 - 509 nm) * Delphinidin-3-O-coumaroylglucoside-pyruvic acid (679 - 511 nm) * Peonidin-3-O-glucoside-pyruvic acid (531 - 509 nm) * Peonidin-3-O-acetylglucoside-pyruvic acid (573 - 510 nm) * Peonidin-3-O-coumaroylglucoside-pyruvic acid (677 - 511 nm) * Petunidin-3-O-glucoside-pyruvic acid (547 - 508 nm) * Petunidin-3-O-acetylglucoside-pyruvic acid (589 - 509 nm) * Petunidin-3-O-coumaroylglucoside-pyruvic acid (693 - 510 nm) * Malvidin-3-O-glucoside-pyruvic acid (561 - 513 nm) * Malvidin-3-O-acetylglucoside-pyruvic acid (603 - 516 nm) * Malvidin-3-O-coumaroylglucoside-pyruvic acid (707 - 513 nm)


Vitisin B type

* Malvidin-3-O-glucoside-acetaldehyde (517 - 490 nm) * Malvidin-3-O-acetylglucoside-acetaldehyde (559 - 494 nm) * Malvidin-3-O-coumaroylglucoside-acetaldehyde (663 - 497 nm)


Oxovitisins

Oxovitisin Oxovitisins are a type of pyranoanthocyanin with a pyranone ( 2-pyrone) component found in aged Port wines. They do not contain an oxonium ion component ( flavylium cation), as anthocyanins do. Therefore, they do not have an absorption maximum at ...
s are
pyranone Pyrones or pyranones are a class of heterocyclic chemical compounds. They contain an unsaturated six-membered ring containing one oxygen atom and a ketone functional group. There are two isomers denoted as 2-pyrone and 4-pyrone. The 2-pyrone (o ...
-anthocyanin derivatives * Pyranone-malvidin-3-glucoside ( Oxovitisin A) * Pyranone-malvidin-3-coumaroylglucoside


Pinotin type

* Delphinidin-3-O-glucoside-4-vinylcatechol (597 - 510 nm) * Delphinidin-3-O-acetylglucoside-4-vinylcatechol (639 - 512 nm) * Delphinidin-3-O-coumaroylglucoside-4-vinylcatechol (743 - 514 nm) * Peonidin-3-O-glucoside-4-vinylcatechol (595 - 504 nm) * Peonidin-3-O-acetylglucoside-4-vinylcatechol (637 - 506 nm) * Peonidin-3-O-coumaroylglucoside-4-vinylcatechol (741 - 508 nm) * Petunidin-3-O-glucoside-4-vinylcatechol (611 - 510 nm) * Petunidin-3-O-acetylglucoside-4-vinylcatechol (653 - 512 nm) * Petunidin-3-O-coumaroylglucoside-4-vinylcatechol (757 - 516 nm) * Malvidin-3-O-glucoside-4-vinylcatechol (625 - 512 nm) * Malvidin-3-O-acetylglucoside-4-vinylcatechol (667 - 514 nm) * Malvidin-3-O-coumaroylglucoside-4-vinylcatechol (771 - 514 nm) * Delphinidin-3-O-glucoside-4-vinylphenol (581 - 504 nm) * Delphinidin-3-O-acetylglucoside-4-vinylphenol (623 - 506 nm) * Delphinidin-3-O-coumaroylglucoside-4-vinylphenol (727 - 506 nm) * Peonidin-3-O-glucoside-4-vinylphenol (579 - 499 nm) * Peonidin-3-O-acetylglucoside-4-vinylphenol (621 - 504 nm) * Peonidin-3-O-coumaroylglucoside-4-vinylphenol (725 - 505 nm) * Petunidin-3-O-glucoside-4-vinylphenol (595 - 504 nm) * Petunidin-3-O-acetylglucoside-4-vinylphenol (636 - 506 nm) * Petunidin-3-O-coumaroylglucoside-4-vinylphenol (741 - 507 nm) * Malvidin-3-O-glucoside-4-vinylphenol (609 - 504 nm) * Malvidin-3-O-acetylglucoside-4-vinylphenol (651 - 507 nm) * Malvidin-3-O-coumaroylglucoside-4-vinylphenol (755 - 509 nm) * Malvidin-3-O-caffeoylglucoside-4-vinylphenol (771 - 532 nm) * Delphinidin-3-O-glucoside-4-vinylguaiacol (611 - 502 nm) * Peonidin-3-O-glucoside-4-vinylguaiacol (609 - 499 nm) * Petunidin-3-O-glucoside-4-vinylguaiacol (625 - 502 nm) * Malvidin-3-O-glucoside-4-vinylguaiacol (639 - 504 nm) * Malvidin-3-O-acetylglucoside-4-vinylguaiacol (681 - 506 nm) * Malvidin-3-O-coumaroylglucoside-vinylguaiacol (755 477 508 nm)


Flavanyl-pyranoanthocyanin type

* Delphinidin-3-O-glucoside-4-vinyl(epi)catechin (777 - 501 nm) * Delphinidin-3-O-acetylglucoside-4-vinyl(epi)catechin (819 - 503 nm) * Peonidin-3-O-glucoside-4-vinyl(epi)catechin (775 - 199 nm) * Peonidin-3-O-acetylglucoside-4-vinyl(epi)catechin (817 - 501 nm) * Petunidin-3-O-glucoside-4-vinyl(epi)catechin (791 - 502 nm) * Petunidin-3-O-acetylglucoside-4-vinyl(epi)catechin (833 - 504 nm) * Malvidin-3-O-glucoside-4-vinyl(epi)catechin (805 - 503 nm) * Malvidin-3-O-acetylglucoside-4-vinyl(epi)catechin (847 - 508 nm) * Malvidin-3-O-coumaroylglucoside-4-vinyl(epi)catechin (951 - 503 nm)Anthocyanins and Their Variation in Red Wines II. Anthocyanin Derived Pigments and Their Color Evolution. Fei He, Na-Na Liang, Lin Mu, Qiu-Hong Pan, Jun Wang, Malcolm J. Reeves and Chang-Qing Duan, Molecules, 2012, 17, pages 1483-1519,


References


See also

*
Phenolic compounds in wine The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include ...
{{Pyranoanthocyanidin