Violdelphin

Violdelphin
Names

IUPAC name 3′,4′,5,5′-Tetrahydroxy-7-(6-O-{4-[6-O-(4-hydroxybenzoyl)-β-D-glucopyranosyloxy]benzoyl}-β-D-glucopyranosyloxy)-3-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]flavylium
Systematic IUPAC name (1²R,1³R,1⁴R,1⁵R,1⁶S,4²R,4³S,4⁴S,4⁵R,4⁶S,8²S,8³R,8⁴S,8⁵S,8⁶R,14²S,14³R,14⁴S,14⁵S,14⁶R)-1³,1⁴,1⁵,4³,4⁴,4⁵,6⁵,8³,8⁴,8⁵,14³,14⁴,14⁵,18⁴-Tetradecahydroxy-1⁶-methyl-11,17-dioxo-6²-(3,4,5-trihydroxyphenyl)-2,5,7,10,13,16-hexaoxa-6¹λ⁴-6(3,7)-[1]benzopyrana-1(2),4,8,14(2,6)-tetrakis(oxana)-12(1,4),18(1)-dibenzenaoctadecaphan-6¹-ylium
Other names Delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-beta-D-glucosyl)oxybenzoyl)-beta-D-glucoside)
Identifiers
CAS Number	126417-59-2
3D model (JSmol)	Interactive image
ChemSpider	2340380
PubChem CID	3083066
CompTox Dashboard (EPA)	DTXSID80155183
InChI InChI=1S/C53H58O30/c1-18-34(58)39(63)43(67)50(76-18)75-17-33-38(62)42(66)46(70)53(83-33)80-30-14-25-26(55)12-24(13-29(25)79-47(30)21-10-27(56)35(59)28(57)11-21)78-52-45(69)41(65)37(61)32(82-52)16-74-49(72)20-4-8-23(9-5-20)77-51-44(68)40(64)36(60)31(81-51)15-73-48(71)19-2-6-22(54)7-3-19/h2-14,18,31-34,36-46,50-53,58,60-70H,15-17H2,1H3,(H4-,54,55,56,57,59,71)/p+1/t18-,31+,32+,33+,34-,36+,37+,38+,39+,40-,41-,42-,43+,44+,45+,46+,50+,51+,52+,53+/m0/s1 Key: YODABPUZPVYDEF-CIBWSIAMSA-O
SMILES CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C([O+]=C4C=C(C=C(C4=C3)O)OC5C(C(C(C(O5)COC(=O)C6=CC=C(C=C6)OC7C(C(C(C(O7)COC(=O)C8=CC=C(C=C8)O)O)O)O)O)O)O)C9=CC(=C(C(=C9)O)O)O)O)O)O)O)O)O
Properties
Chemical formula	C₅₃H₅₉O₃₀+
Molar mass	1176.02 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Violdelphin is an anthocyanin, a plant pigment, has been found in the purplish blue flower of Aconitum chinense,^[1] in the blue flowers in the genus Campanula^[2] and in the blue flowers of Delphinium hybridum.^[3] It is a flavenoid natural product, incorporating two p-hydroxy benzoic acid residues, one rutinoside and two glucosides associated with a delphinidin.

References

^ The anthocyanin responsible for purplish blue flower colour of Aconitum chinense. Kosaku Takeda, Syuji Sato, Hiromitsu Kobayashi, Yoko Kanaitsuka, Mariko Ueno, Takeshi Kinoshita, Hiroyuki Tazaki and Takane Fujimori, Phytochemistry, June 1994, Volume 36, Issue 3, Pages 613–616, doi:10.1016/S0031-9422(00)89784-8
^ Structure and biosynthesis of anthocyanins in flowers of Campanula. Kirsten Brandt, Tadao Kondo, Hideki Aoki and Toshio Goto, Phytochemistry, 29 April 1993, Volume 33, Issue 1, Pages 209–212, doi:10.1016/0031-9422(93)85424-P
^ Structure of Violdelphin, an Anthocyanin from Violet Flower of Delphinium hybridum. Tadao Kondo, Kaori Oki, Kumi Yoshida and Toshio Goto, Chemistry Letters,1990, Vol. 19, No. 1, pages 137-138, doi:10.1246/cl.1990.137

Anthocyanidins and their anthocyanin glucosides

3-Hydroxyanthocyanidins

3-Deoxyanthocyanidins

O-Methylated anthocyanidins

Anthocyanins
(anthocyaninidin glycosides)

Glucosides:

Callistephin (Pelargonidin 3-O-glucoside)
Chrysanthemin (Cyanidin 3-O-glucoside)
Myrtillin (Delphinidin 3-O-glucoside)
Oenin (Malvidin 3-O-glucoside)
Peonidin 3-O-glucoside
Petunidin 3-O-glucoside
Pulchellidin 3-glucoside

Diglucosides:

Cyanin (Cyanidin 3,5-O-diglucoside)
Delphin (Delphinidin 3,5-O-diglucoside)
Malvin (Malvidin 3,5-diglucoside)
Pelargonin (Pelargonidin 3,5-O-diglucoside)
Peonin (Peonidin 3,5-O-diglucoside)
Petunin (Petunidin 3,5-O-diglucoside)

Others glycosides:

Antirrhinin (Cyanidin 3-O-rutinoside)
Ideain (Cyanidin 3-O-galactoside)
Delphinidin 3-O-rhamnoside
Petunidin 3-O-arabinoside
Petunidin 3-O-galactoside
Petunidin 3-O-rhamnoside
Petunidin 3-O-rutinoside
Primulin (Malvidin 3-O-galactoside)
Pulchellidin 3-rhamnoside
Tulipanin (Delphinidin 3-O-rutinoside)

Acylated anthocyanins

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 Delphinidin 3-O-(6-p-coumaroyl)glucoside Malvidin 3-O-(6-p-coumaroyl)glucoside 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
Malonylated anthocyanins	Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)
Acylated anthocyanin diglycosides	Cyanidin 3-O-(di-p-coumarylglucoside)-5-glucoside Gentiodelphin (delphinidin 3-''O''-glucosyl-5-''O''-(6-''O''-caffeoyl-glucosyl)-3′-''O''-(6-''O''-caffeoyl-glucoside)) Nasunin (Delphinidin 3-(p-coumaroylrutinoside)-5-glucoside) Petanin (petunidin 3-[6-O-(4-O-(E)-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-D-glucopyranoside]-5-O-β-D-glucopyranoside) Violdelphin (Delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-β-D-glucosyl)oxybenzoyl)-β-D-glucoside)