Delphinidin-3-O-(6-p-coumaroyl)glucoside

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Delphinidin-3-O-(6-p-coumaroyl)glucoside - Wikipedia

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Delphinidin-3-O-(6-p-coumaroyl)glucoside
Names

IUPAC name 3′,4′,5,5′,7-Pentahydroxy-3-{6-O-[3-(4-hydroxyphenyl)prop-2-enoyl]-β-D-galactopyranosyloxy}flavylium
Systematic IUPAC name (4²S,4³R,4⁴S,4⁵S,4⁶R,8E)-1³,1⁴,1⁵,2⁵,2⁷,4³,4⁴,4⁵,10⁴-Nonahydroxy-7-oxo-3,6-dioxa-2¹λ⁴-2(2,3)-[1]benzopyrana-4(2,6)-oxana-1,10(1)-dibenzenadecaphan-8-en-2¹-ylium
Other names Delphinidin-3-O-p-coumaroyl glucoside
Identifiers
CAS Number	339080-03-4^[1]^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:75677
ChemSpider	26559505
KEGG	C16370
PubChem CID	15922818
CompTox Dashboard (EPA)	DTXSID801030109
InChI InChI=1S/C30H26O14/c31-15-4-1-13(2-5-15)3-6-24(36)41-12-23-26(38)27(39)28(40)30(44-23)43-22-11-17-18(33)9-16(32)10-21(17)42-29(22)14-7-19(34)25(37)20(35)8-14/h1-11,23,26-28,30,38-40H,12H2,(H5-,31,32,33,34,35,36,37)/p+1/t23-,26-,27+,28-,30-/m1/s1 Key: DHTPVCYNNWQRMN-LHRGPQAGSA-O InChI=1/C30H26O14/c31-15-4-1-13(2-5-15)3-6-24(36)41-12-23-26(38)27(39)28(40)30(44-23)43-22-11-17-18(33)9-16(32)10-21(17)42-29(22)14-7-19(34)25(37)20(35)8-14/h1-11,23,26-28,30,38-40H,12H2,(H5-,31,32,33,34,35,36,37)/p+1/t23-,26-,27+,28-,30-/m1/s1 Key: DHTPVCYNNWQRMN-LEURJHHLBH
SMILES c1cc(ccc1/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)Oc3cc4c(cc(cc4[o+]c3c5cc(c(c(c5)O)O)O)O)O)O)O)O)O
Properties
Chemical formula	C ₃₀H ₂₇O⁺ ₁₄
Molar mass	611.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Delphinidin 3-O-(6-p-coumaroyl)glucoside is a p-coumaroylated anthocyanin. It can be found in some red Vitis vinifera grape cultivars (like Graciano^[2]) and in red wine.^[3]

References

^ "Showing Compound Delphinidin 3-(6-p-coumaroylglucoside) (FDB017204) - FooDB". foodb.ca.
^ Núñez, V.; Monagas, M.; Gomez Cordovés, M. C.; Bartolomé, B. (2004). "Vitis vinifera L. cv. Graciano grapes characterized by its anthocyanin profile". Postharvest Biology and Technology. 31: 69–79. doi:10.1016/S0925-5214(03)00140-6.
^ "Delphinidin 3-(6-p-coumaroyl)glucoside on www.phenol-explorer.eu". Archived from the original on 2011-12-30. Retrieved 2012-02-21.
^ Delphinidin 3-(6-p-coumaroyl)glucoside synthesis reaction on www.kegg.jp

3-Hydroxyanthocyanidins

O-Methylated anthocyanidins

Anthocyanins
(anthocyaninidin glycosides)

Glucosides:

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:

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)

Miscellaneous

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