Echinacoside

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.^[1] 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.

Echinacoside

Names
IUPAC name 2-(3,4-Dihydroxyphenyl)ethyl α-L-rhamnopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside 4-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate]
Systematic IUPAC name (2R,3R,4R,5R,6R)-5-Hydroxy-2-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Identifiers
CAS Number	82854-37-3 Y
3D model (JSmol)	Interactive image
ChemSpider	4445084 N
ECHA InfoCard	100.127.421
PubChem CID	5281771
UNII	I04O1DT48T Y
CompTox Dashboard (EPA)	DTXSID0033469
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 N Key: FSBUXLDOLNLABB-ISAKITKMSA-N 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). N verify (what is YN ?) Infobox references

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.^[2]

References

1. Bernaś, Urszula; Hajmowicz, Halina; Madura, Izabela D.; Majcher, Monika; Synoradzki, Ludwik; Zawada, Krzysztof (2010). "Tartaric acid and its acyl derivatives. Part 5. Direct synthesis of monoacyltartaric acids and novel mono(benzoyl)tartaric anhydride: unusual findings in tartaric acid acylation". Arkivoc. 2010 (11): 1–12. doi:10.3998/ark.5550190.0011.b01. hdl:2027/spo.5550190.0011.b01.
2. 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.