Primulin (anthocyanin)

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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.045.490 Edit this at Wikidata
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
C23H25ClO12
C23H25O12+
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).
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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]

  1. ^ Primulin Yellow on chemicalregister.com
  2. ^ J. B. Harborne; H. S. A. Sherratt (1961). "Plant Polyphenols: 3. Flavonoids in genotypes of Primula sinensis" (PDF). Biochem. J. 78 (2): 298–306. doi:10.1042/bj0780298. PMC 1205266. PMID 13711452.
  3. ^ Rose Scott-Moncrieff and the dawn of (Bio) Chemical Genetics, Cathie Martin, April 2016, Biochemical classics, Biochemist.org, Retrieved 5 July 2016