Delphinidin

Delphinidin

Names
IUPAC name 2-(3,4,5-Trihydroxyphenyl)chromenylium-3,5,7-triol
Identifiers
CAS Number	13270-61-6 528-53-0 (chloride)
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:28436
ChEMBL	ChEMBL590878 ChEMBL276780
ChemSpider	114185
ECHA InfoCard	100.007.671
PubChem	68245
InChI InChI=1S/C15H10O7.ClH/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6;/h1-5H,(H5-,16,17,18,19,20,21);1H Key: FFNDMZIBVDSQFI-UHFFFAOYSA-N InChI=1/C15H10O7.ClH/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6;/h1-5H,(H5-,16,17,18,19,20,21);1H Key: FFNDMZIBVDSQFI-UHFFFAOYAW
SMILES Oc3cc(O)cc(c3CC2O)OC2c(cc1O)cc(O)c1O [Cl-].Oc1cc(cc(O)c1O)c3[o+]c2cc(O)cc(O)c2cc3O
Properties
Chemical formula	C15H11O7^+
Molar mass	303.24 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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Infobox references

Delphinidin (also delphinidine^[1][2]) is an anthocyanidin, a primary plant pigment, and also an antioxidant.^[3] Delphinidin gives blue hues to flowers in the genera Viola and Delphinium. It also gives the blue-red color of the grape that produces Cabernet Sauvignon, and can be found in cranberries and Concord grapes as well as pomegranates,^[4] and bilberries.^[5]

Delphinidin, like nearly all other anthocyanidins, is pH-sensitive, ie. a natural pH indicator, and changes from red in acidic solution to blue in basic solution.

Glycosides

Several glycosides derived from delphinidin are known.

Myrtillin (delphinidin-3-O-glucoside) and tulipanin (delphinidin-3-O-rutinoside) can be found in blackcurrant pomace.

Violdelphin (delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-β-D-glucosyl)oxybenzoyl)-β-D-glucoside) is responsible for purplish blue flower color of Aconitum chinense.^[6]
Nasunin (delphinidin-3-(p-coumaroylrutinoside)-5-glucoside) is responsible for the colour of the eggplant fruit purple skin.^[7]

See also

• Prodelphinidin, a type of condensed tannins

References

1. "Delphinidine".
2. "Delphinidine".
3. Afaq, F.; Syed, D. N.; Malik, A.; Hadi, N.; Sarfaraz, S.; Kweon, M.-H.; Khan, N.; Zaid, M. A.; Mukhtar, H. (2007). "Delphinidin, an Anthocyanidin in Pigmented Fruits and Vegetables, Protects Human HaCaT Keratinocytes and Mouse Skin Against UVB-Mediated Oxidative Stress and Apoptosis". Journal of Investigative Dermatology. 127 (1): 222–232. doi:10.1038/sj.jid.5700510. PMID 16902416.
4. Ribéreau-Gayon, J.; Ribéreau-Gayon, P. (1958). "The Anthocyans and Leucoanthocyans of Grapes and Wines". American Journal of Enology and Viticulture. 9: 1–9.
5. Lätti AK, Riihinen KR, Kainulainen PS (2008). "Analysis of anthocyanin variation in wild populations of bilberry (Vaccinium myrtillus L.) in Finland". J Agric Food Chem. 56 (1): 190–6. doi:10.1021/jf072857m. PMID 18072741.
6. CID 3083066 from PubChem
7. Antioxidant activity of nasunin, an anthocyanin in eggplant peels. Noda Y, Kneyuki T, Igarashi K, Mori A and Packer L, Toxicology, 7 Aug 2000, volume 148, issues 2-3, pages 119-123, PMID 10962130, doi:10.1016/S0300-483X(00)00202-X