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Delphinidin

Names
IUPAC name 3,3′,4′,5,5′,7-Hexahydroxyflavylium
Systematic IUPAC name 3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-1λ-1-benzopyran-1-ylium
Identifiers
CAS Number	13270-61-6 528-53-0 (chloride)
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28436
ChEMBL	ChEMBL590878 ChEMBL276780
ChemSpider	114185
ECHA InfoCard	100.007.671
E number	E163b (colours)
KEGG	C05908
PubChem CID	68245
UNII	031A4BN94T EM6MD4AEHE (chloride)
CompTox Dashboard (EPA)	DTXSID701019982
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);1HKey: 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);1HKey: FFNDMZIBVDSQFI-UHFFFAOYAW
SMILES C1=C(C=C(C(=C1O)O)O)C2=C(C=C3C(=CC(=CC3=2)O)O)O.
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 , 100 kPa). N verify (what is  ?) Infobox references

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

Delphinidin, like nearly all other anthocyanidins, is pH-sensitive, i.e. a natural pH indicator, and changes from blue in basic solution to red in acidic 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 the purplish-blue flower color of Aconitum chinense.
• Nasunin (delphinidin-3-(p-coumaroylrutinoside)-5-glucoside) is responsible for the colour of the eggplant fruit's purple skin.
• Delphinidin ternatins including Clitoria ternatea ternatins

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. Noda Y, Kneyuki T, Igarashi K, Mori A, Packer L (2000). "Antioxidant activity of nasunin, an anthocyanin in eggplant peels". Toxicology. 148 (2–3): 119–23. doi:10.1016/s0300-483x(00)00202-x. PMID 10962130.{{cite journal}}: CS1 maint: multiple names: authors list (link)

• Anthocyanidins