Delphinidin

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Delphinidin

IUPAC name 2-(3,4,5-Trihydroxyphenyl)chromenylium-3,5,7-triol
Identifiers
CAS number	13270-61-6^Y, 528-53-0 (chloride)
PubChem	68245
ChemSpider	114185^N
ChEBI	CHEBI:28436^N
ChEMBL	CHEMBL590878^Y, CHEMBL276780
Jmol-3D images	{{#if:Oc3cc(O)cc(c3CC2O)OC2c(cc1O)cc(O)c1O[Cl-].Oc1cc(cc(O)c1O)c3[o+]c2cc(O)cc(O)c2cc3O\|Image 1 Image 2
SMILES Oc3cc(O)cc(c3CC2O)OC2c(cc1O)cc(O)c1O [Cl-].Oc1cc(cc(O)c1O)c3[o+]c2cc(O)cc(O)c2cc3O
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^Y Key: FFNDMZIBVDSQFI-UHFFFAOYSA-N^Y 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
Properties
Molecular formula	C₁₅H₁₁O₇⁺
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Delphinidin is an anthocyanidin, a primary plant pigment, and also an antioxidant.^[1] 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.^[2] Delphinidin, like nearly all other anthocyanidins, is pH-sensitive, 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 purplish blue flower color of Aconitum chinense.^[3]

References

↑ 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.
↑ Ribéreau-Gayon, J.; Ribéreau-Gayon, P. (1958). "The Anthocyans and Leucoanthocyans of Grapes and Wines". American Journal of Enology and Viticulture 9: 1–9.
↑ PubChem 3083066

v t e Anthocyanidins and their anthocyanin glucosides

3-hydroxyanthocyanidins	5-Desoxy-peonidin Aurantinidin Cyanidin 6-Hydroxycyanidin Delphinidin Fisetinidin Guibourtinidin Pelargonidin Robinetinidin

3-deoxyanthocyanidins	Apigeninidin Columnidin Diosmetinidin Gesneridin Luteolinidin Tricetinidin

O-methylated anthocyanidins	5-Desoxy-malvidin Capensinidin Europinidin Hirsutidin Malvidin Peonidin Petunidin Pulchellidin Rosinidin

Anthocyanins	Antirrhinin (Cyanidin-3-O-rutinoside) Callistephin (Pelargonidin 3-O-glucoside) Chrysanthemin (Cyanidin-3-O-glucoside) Malvin (Malvidin 3,5-diglucoside) Myrtillin (Delphinidin-3-O-glucoside) Oenin (Malvidin-3-O-glucoside) Peonidin-3-O-glucoside Petunidin 3,5-O-diglucoside Petunidin 3-O-arabinoside Petunidin 3-O-galactoside Petunidin-3-O-glucoside Petunidin 3-O-rhamnoside Petunidin-3-O-rutinoside Primulin (Malvidin-3-O-galactoside) Pulchellidin 3-glucoside Pulchellidin 3-rhamnoside Tulipanin (Delphinidin 3-O-rutinoside)

Acetylated anthocyanins	Cyanidin-3-O-(6-acetyl)-glucoside Delphinidin-3-O-(6-acetyl)-glucoside Malvidin-3-O-(6-acetyl)-glucoside Petunidin-3-O-(6-acetyl)-galactoside Petunidin-3-O-(6-acetyl)-glucoside Peonidin-3-O-(6-acetyl)-glucoside

Coumaroylated anthocyanins (cis- and trans-)	Cyanidin-3-O-(6-p-coumaroyl)glucoside Cyanidin-3-O-(di-p-coumarylglucoside)-5-glucoside Delphinidin-3-O-(6-p-coumaroyl)glucoside Malvidin-3-O-(6-p-coumaroyl)glucoside Petanin (petunidin 3-[6-O-(4-O-E-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-d-glucopyranoside]-5-O-β-d-glucopyranoside) Petunidin-3-O-(6-p-coumaroyl)glucoside Peonidin-3-O-(6-p-coumaroyl)glucoside

Caffeoylated anthocyanins	Malvidin-3-O-(6-p-caffeoyl)glucoside Peonidin-3-O-(6-p-caffeoyl)glucoside Gentiodelphin (delphinidin 3-O-glucosyl-5-O-(6-O-caffeoyl-glucosyl)-3′-O-(6-O-caffeoyl-glucoside))

p-hydroxybenzoylated anthocyanins	Violdelphin

Flavanol-anthocyanin adducts	Malvidin glucoside-ethyl-catechin

Misc.	Metalloanthocyanins (Commelinin Cyanosalvianin Protocyanin Protodelphin) Pyranoanthocyanins Copigmentation

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Delphinidin

Glycosides

See also

References