Primulin (anthocyanin) (original) (raw)

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Primulin
Names
IUPAC name (2_S_,3_R_,4_S_,5_R_,6_R_)-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol chloride
Other namesMalvidin 3-galactosideMalvidin-3-galactoside chlorideMalvidin-3-O-galactosideMalvidin-3-O-galactoside chloride3-(Galactosyloxy)-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1-benzopyrylium chloridePrimulin Yellow[1]
Identifiers
CAS Number 30113-37-2 checkY
3D model (JSmol) Interactive image
ChemSpider 85201
ECHA InfoCard 100.045.490 Edit this at Wikidata
PubChem CID 94409
UNII MB4022065G checkY
CompTox Dashboard (EPA) DTXSID90952524 Edit this at Wikidata
InChI 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/s1Key: PXUQTDZNOHRWLI-XSEKTIEYSA-OInChI=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/s1Key: PXUQTDZNOHRWLI-IRUYQYSKBI
SMILES 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
Chemical formula C23H25ClO12C23H25O12+
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). checkY verify (what is checkY☒N ?) Infobox references

Chemical compound

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