Anthocyanone A
Anthocyanone A
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Names
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IUPAC name
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2-(2,6-dihydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)acetate
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Other names
8-β-d-glucopyranosyl-2,4-dihydroxy-6-oxo-cyclohexa-2,4-dienyl acetic acid
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Identifiers
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ChemSpider
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InChI=1S/C14H16O10/c15-4-9-11(20)12(21)13(22)14(23-9)24-10(19)3-6-7(17)1-5(16)2-8(6)18/h1-3,9,11-17,20-22H,4H2/b6-3+/t9-,11-,12+,13-,14+/m1/s1 Key: VOWKJMFKRCLSJJ-BFYJNFCASA-N InChI=1/C14H16O10/c15-4-9-11(20)12(21)13(22)14(23-9)24-10(19)3-6-7(17)1-5(16)2-8(6)18/h1-3,9,11-17,20-22H,4H2/b6-3+/t9-,11-,12+,13-,14+/m1/s1 Key: VOWKJMFKRCLSJJ-BFYJNFCABS
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C1=C(C=C(/C(=C\C(=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)/C1=O)O)O
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Properties
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C14H16O10
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Molar mass
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344.272 g·mol−1
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Anthocyanone A is a degradation product of malvidin 3-O-glucoside under acidic conditions.[1] It is found in wine.[2]
References
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3-Hydroxyanthocyanidins | |
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3-Deoxyanthocyanidins | |
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O-Methylated anthocyanidins | |
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Anthocyanins (anthocyaninidin glycosides) | Glucosides:
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)
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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
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Coumaroylated anthocyanins (cis- and trans-) | |
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Caffeoylated anthocyanins |
- Malvidin 3-O-(6-p-caffeoyl)glucoside
- Peonidin 3-O-(6-p-caffeoyl)glucoside
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Malonylated anthocyanins |
- Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)
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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)
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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
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Miscellaneous | |
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