Primulin
Names
IUPAC name
(2S ,3R ,4S ,5R ,6R )-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol chloride
Other names
Malvidin 3-galactoside
Malvidin-3-galactoside chloride
Malvidin-3-O-galactoside
Malvidin-3-O-galactoside chloride
3-(Galactosyloxy)-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1-benzopyrylium chloride
Primulin Yellow
[ 1]
Identifiers
ChemSpider
ECHA InfoCard
100.045.490
UNII
InChI=1S/C23H24O12/c1-31-14-3-9(4-15(32-2)18(14)27)22-16(7-11-12(26)5-10(25)6-13(11)33-22)34-23-21(30)20(29)19(28)17(8-24)35-23/h3-7,17,19-21,23-24,28-30H,8H2,1-2H3,(H2-,25,26,27)/p+1/t17-,19+,20+,21-,23-/m1/s1
Key: PXUQTDZNOHRWLI-XSEKTIEYSA-O
InChI=1/C23H24O12/c1-31-14-3-9(4-15(32-2)18(14)27)22-16(7-11-12(26)5-10(25)6-13(11)33-22)34-23-21(30)20(29)19(28)17(8-24)35-23/h3-7,17,19-21,23-24,28-30H,8H2,1-2H3,(H2-,25,26,27)/p+1/t17-,19+,20+,21-,23-/m1/s1
Key: PXUQTDZNOHRWLI-IRUYQYSKBI
COc1cc(cc(c1O)OC)c2c(cc3c(cc(cc3[o+]2)O)O)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O
Properties
C23 H25 ClO12 C23 H25 O12 +
Molar mass
528.89 g/mol (chloride) 493.43 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Primulin is an anthocyanin . It is the 3-galactoside of malvidin . It can be found in Primula sinensis .[ 2]
The first crystalline form of this pigment was prepared by Rose Scott-Moncrieff in about 1930. This was the first crystalline anthocyanin pigment ever identified. This was possible because of her insight into linking genetics with chemistry.[ 3]
References
3-Hydroxyanthocyanidins 3-Deoxyanthocyanidins O -Methylated anthocyanidinsAnthocyanins (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)
Idaein (Cyanidin 3-O -galactoside)
Delphinidin 3-O -rhamnoside
Petunidin 3-O -arabinoside
Petunidin 3-O -galactoside
Petunidin 3-O -rhamnoside
Petunidin 3-O -rutinoside
(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 -) 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