Delphinidin

Delphinidin
Names
	IUPAC name 3,3′,4′,5,5′,7-Hexahydroxyflavylium
	Systematic IUPAC name 3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-1λ4-1-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);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 C1=C(C=C(C(=C1O)O)O)C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)O.[Cl-];
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). verify (what is ?) 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 variety 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, 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.^[6]
Nasunin (delphinidin-3-(p-coumaroylrutinoside)-5-glucoside) is responsible for the colour of the eggplant fruit's purple skin.^[7]
Delphinidin ternatins including Clitoria ternatea ternatins

References

^ "Delphinidine".
^ "Delphinidine".
^ 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.
^ 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.
^ CID 3083066 from PubChem
^ 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)

[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)

[1]

[2]

[3]

[4]

[5]

[6]

[7]

Glycosides

See also

References