Echinacoside

Echinacoside

Names
IUPAC name [(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl](E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Identifiers
CAS Number	82854-37-3=
ChemSpider	4445084
Jmol interactive 3D	Image
PubChem	5281771
InChI InChI=1S/C35H46O20/c1-14-24(42)26(44)29(47)35(51-14)55-32-30(48)34(49-9-8-16-3-6-18(38)20(40)11-16)53-22(13-50-33-28(46)27(45)25(43)21(12-36)52-33)31(32)54-23(41)7-4-15-2-5-17(37)19(39)10-15/h2-7,10-11,14,21-22,24-40,42-48H,8-9,12-13H2,1H3/b7-4+/t14-,21+,22+,24-,25+,26+,27-,28+,29+,30+,31+,32+,33+,34+,35-/m0/s1 Key: FSBUXLDOLNLABB-ISAKITKMSA-N InChI=1/C35H46O20/c1-14-24(42)26(44)29(47)35(51-14)55-32-30(48)34(49-9-8-16-3-6-18(38)20(40)11-16)53-22(13-50-33-28(46)27(45)25(43)21(12-36)52-33)31(32)54-23(41)7-4-15-2-5-17(37)19(39)10-15/h2-7,10-11,14,21-22,24-40,42-48H,8-9,12-13H2,1H3/b7-4+/t14-,21+,22+,24-,25+,26+,27-,28+,29+,30+,31+,32+,33+,34+,35-/m0/s1 Key: FSBUXLDOLNLABB-ISAKITKMBV
SMILES C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/c3ccc(c(c3)O)O)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OCCc5ccc(c(c5)O)O)O)O)O)O
Properties
Chemical formula	C35H46O20
Molar mass	786,73 g/mol
Melting point	200 to 220 °C (392 to 428 °F; 473 to 493 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Echinacoside is a natural phenol. It is a caffeic acid glycoside from the phenylpropanoid class. It is constituted from a trisaccharide consisting of two glucose and one rhamnose moieties glycosidically linked to one caffeic acid and one dihydroxyphenylethanol (hydroxytyrosol) residue at the centrally situated rhamnose. This water-soluble glycoside is a distinctive secondary metabolite of Echinacea angustifolia and Echinacea pallida (to about 1%) but only occurs in trace amounts in Echinacea purpurea. It is also isolated from Cistanche spp.

It was first isolated by Stoll et al. in 1950 from the roots of Echinacea angustifolia. It shows weak antibiotic activity in vitro against Staphylococcus aureus and Streptococci.^[1]

References

1. Stoll, A.; Renz, J.; Brack, A. (1950). "Isolierung und Konstitution des Echinacosids, eines Glykosids aus den Wurzeln von Echinacea angustifolia D. C. 6. Mitteilung über antibakterielle Stoffe". Helvetica Chimica Acta 33 (6): 1877–1893. doi:10.1002/hlca.19500330657.