Delphinidin

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 414413412 | ImageFile=Delphinidin.svg | ImageSize=200px | ImageClass=skin-invert-image | IUPACName=3,3′,4′,5,5′,7-Hexahydroxyflavylium | SystematicName=3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-1λ4-1-benzopyran-1-ylium | OtherNames= |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 114185 | 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 | InChIKey = FFNDMZIBVDSQFI-UHFFFAOYAW | SMILES = C1=C(C=C(C(=C1O)O)O)C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)O.[Cl-] | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 28436 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 590878 | ChEMBL2_Ref = {{ebicite|changed|EBI}} | ChEMBL2 = 276780 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = FFNDMZIBVDSQFI-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo=13270-61-6 | CASNo1_Ref = {{cascite|correct|CAS}} | CASNo1=528-53-0 | CASNo1_Comment = (chloride) | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 031A4BN94T | UNII1_Ref = {{fdacite|correct|FDA}} | UNII1 = EM6MD4AEHE | UNII1_Comment = (chloride) | PubChem = 68245 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C05908 }} |Section2={{Chembox Properties | Formula=C15H11O7+ | MolarMass = 303.24 g/mol | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= }} |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} }}

'''Delphinidin''' (also '''delphinidine'''<ref>{{cite web | url = https://www.chemindustry.com/chemicals/0934666.html | title = Delphinidine }}</ref><ref>{{cite web | url = http://en.chembase.cn/substance-136982.html | title = Delphinidine }}</ref>) is an anthocyanidin, a primary plant pigment, and also an antioxidant.<ref>{{cite journal | title = Delphinidin, an Anthocyanidin in Pigmented Fruits and Vegetables, Protects Human HaCaT Keratinocytes and Mouse Skin Against UVB-Mediated Oxidative Stress and Apoptosis |author1=Afaq, F. |author2=Syed, D. N. |author3=Malik, A. |author4=Hadi, N. |author5=Sarfaraz, S. |author6=Kweon, M.-H. |author7=Khan, N. |author8=Zaid, M. A. |author9=Mukhtar, H. | journal = Journal of Investigative Dermatology | year = 2007 | volume = 127 | issue = 1 | pages = 222–232 | doi = 10.1038/sj.jid.5700510 | pmid = 16902416 |doi-access=free }}</ref> 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,<ref>{{ cite journal |author1=Ribéreau-Gayon, J. |author2=Ribéreau-Gayon, P. | title = The Anthocyans and Leucoanthocyans of Grapes and Wines | journal = American Journal of Enology and Viticulture | year = 1958 | volume = 9 | pages = 1–9 }}</ref> and bilberries.<ref>{{cite journal |journal=J Agric Food Chem|vauthors=Lätti AK, Riihinen KR, Kainulainen PS |title=Analysis of anthocyanin variation in wild populations of bilberry (Vaccinium myrtillus L.) in Finland |year=2008 |volume=56 |issue=1|pages=190–6 |pmid=18072741 |doi=10.1021/jf072857m}}</ref>

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. {{Ph indicator template|high_pH=11|high_pH_color=blue|indicator_name=Delfinidin|low_pH=3|low_pH_text=white|low_pH_color=red|high_pH_text=white}}

== 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''.<ref>{{PubChem|3083066}}</ref> *Nasunin (delphinidin-3-(''p''-coumaroylrutinoside)-5-glucoside) is responsible for the colour of the eggplant fruit's purple skin.<ref>{{cite journal | pmid = 10962130 | volume=148 | title=Antioxidant activity of nasunin, an anthocyanin in eggplant peels | year=2000 | journal=Toxicology | pages=119–23 | author=Noda Y, Kneyuki T, Igarashi K, Mori A, Packer L | issue=2–3 | doi=10.1016/s0300-483x(00)00202-x }}</ref> *{{visible anchor|Delphinidin ternatin}}s including ''Clitoria ternatea'' ternatins

== See also == * Prodelphinidin, a type of condensed tannins

==References== {{reflist}}

Category:Anthocyanidins