Idaein

Idaein
Structure of ideain chloride
Names
IUPAC name
(2S,4S,5R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride
Other names
Ideain, cyanidin 3-O-galactoside, Cy3Gal
Identifiers
3D model (JSmol)
ChemSpider
KEGG
UNII
  • InChI=1S/C21H20O11.ClH/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8;/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26);1H/t16?,17-,18-,19?,21+;/m0./s1
    Key: YTMNONATNXDQJF-DJBUQWCWSA-N
  • C1=CC(=C(C=C1C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O.[Cl-]
Properties
C21H21ClO11 (chloride), C21H21O11+ (cation)
Molar mass 484.83 g/mol (chloride), 449.38 g/mol (cation)
UV-vis (λmax) 528 nm (in methanol)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Idaein, also known as ideain, cyanidin 3-O-galactoside, or Cy3Gal, is a type of anthocyanin, a class of plant pigment compounds.

Natural occurrences

Idaein is the main anthocyanin compound in lingonberries (Vaccinium vitis-idaea), and the name of the compound is derived from the Latin name of the plant. It is also present as one of the many anthocyanins compounds found in bilberries (Vaccinium myrtillus) and cranberries (Vaccinium macrocarpon).

Idaein is the main anthocyanin in red-skinned or red-fleshed (for example Weirouge or Surprise) apple varieties. It is also found in Chinese hawthorn fruits (Crataegus spp.). It is also the pigment in the copper beech (cultivar of Fagus sylvatica), that was identified in 1932.

Quintinia serrata, the tawheowheo, a species of evergreen trees endemic to New Zealand, has different patterns of anthocyanins (cyanidin 3-O-glucoside and cyanidin 3-O-galactoside) in its leaves to protect the shade-adapted chloroplasts from direct sunlight.

References

  1. 1 2 Willstätter, Richard; Mallison, Heinrich (1915). "Untersuchungen über die Anthocyane. III. Über den Farbstoff der Preiselbeere" [Studies on anthocyanins. III. On the pigment of lingonberries]. Justus Liebigs Annalen der Chemie. 408 (1): 15–41. doi:10.1002/jlac.19154080103.
  2. ↑ Lehtonen, Henna-Maria; Rantala, Milla; Suomela, Jukka-Pekka; Viitanen, Matti; Kallio, Heikki (2009). "Urinary excretion of the main anthocyanin in lingonberry (Vaccinium vitis-idaea), cyanidin 3-O-galactoside, and its metabolites". Journal of Agricultural and Food Chemistry. 57 (10): 4447–4451. doi:10.1021/jf900894k.
  3. ↑ Grove, Kathryn E.; Robinson, Robert (1931). "An anthocyanin of Oxycoccus macrocarpus Pers". Biochemical Journal. 25 (5): 1706–1711. doi:10.1042/bj0251706. PMC 1260798. PMID 16744736.
  4. ↑ Baj, A; Bombardelli, E; Gabetta, B; Martinelli, EM (1983). "Qualitative and quantitative evaluation of Vaccinium myrtillus anthocyanins by high-resolution gas chromatography and high-performance liquid chromatography". Journal of Chromatography A. 279: 365–372. doi:10.1016/S0021-9673(01)93636-2.
  5. ↑ Ohnishi, Ryoko; Ito, Hideyuki; Kasajima, Naoki; Kaneda, Miyuki; Kariyama, Reiko; Kumon, Hiromi; Hatano, Tsutomu; Yoshida, Takashi (2006). "Urinary excretion of anthocyanins in humans after cranberry juice ingestion". Bioscience, Biotechnology, and Biochemistry. 70 (7): 1681–1687. doi:10.1271/bbb.60023.
  6. ↑ Sadilova, E; Stintzing, FC; Carle, R (2012). "Chemical quality parameters and anthocyanin pattern of red-fleshed Weirouge apples". Journal of Applied Botany and Food Quality. 80 (1): 82–87. doi:10.5073/JABFQ.2006.080.012.
  7. ↑ Würdig, Juliane; Flachowsky, Henryk; Höfer, Monika; Peil, Andreas; Eldin Ali, Mohammed Ali Mohammed Saad; Hanke, Magda-Viola (2014). "Phenotypic and genetic analysis of the German Malus Germplasm Collection in terms of type 1 and type 2 red-fleshed apples". Gene. 544 (2): 198–207. doi:10.1016/j.gene.2014.04.045. PMID 24768720.
  8. ↑ Sato, Hideto; Otagaki, Shungo; Saelai, Parichat; Kondo, Satoru; Shiratake, Katsuhiro; Matsumoto, Shogo (2017). "Varietal differences in phenolic compounds metabolism of type 2 red-fleshed apples" (PDF). Scientia Horticulturae. 219: 1–9. Bibcode:2017ScHor.219....1S. doi:10.1016/j.scienta.2017.02.041.
  9. ↑ Liang, Zhongxin; Liang, Hongrui; Guo, Yizhan; Yang, Dong (2021). "Cyanidin 3-O-galactoside: A natural compound with multiple health benefits". International Journal of Molecular Sciences. 22 (5): 2261. doi:10.3390/ijms22052261. PMC 7956414. PMID 33668383.
  10. ↑ Liu, Pengzhan; Kallio, Heikki; Lü, Deguo; Zhou, Chuansheng; Yang, Baoru (2011). "Quantitative analysis of phenolic compounds in Chinese hawthorn (Crataegus spp.) fruits by high performance liquid chromatography–electrospray ionisation mass spectrometry". Food Chemistry. 127 (3): 1370–1377. doi:10.1016/j.foodchem.2011.01.103.
  11. ↑ Robinson, R; Smith, H (1955). "Anthocyanins of the leaf of the copper beech (Fagus sylvatica) and the fruit of the cultivated strawberry (Fragaria virginiana)". Nature. 175 (4458): 634. doi:10.1038/175634a0.
  12. ↑ Gould, Kevin S; Markham, Kenneth R; Smith, Richard H; Goris, Jessica J (2000). "Functional role of anthocyanins in the leaves of Quintinia serrata A. Cunn". Journal of Experimental Botany. 51 (347): 1107–1115. doi:10.1093/jexbot/51.347.1107.