{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 414920078 | Name = Echinacoside | ImageFile = Echinacoside.svg | ImageSize = | ImageName = Chemical structure of echinacoside | ImageAlt = Chemical structure of echinacoside | IUPACName = 2-(3,4-Dihydroxyphenyl)ethyl α-<small>L</small>-rhamnopyranosyl-(1→3)-[β-<small>D</small>-glucopyranosyl-(1→6)]-β-<small>D</small>-glucopyranoside 4-[(2''E'')-3-(3,4-dihydroxyphenyl)prop-2-enoate] | SystematicName = (2''R'',3''R'',4''R'',5''R'',6''R'')-5-Hydroxy-2-({[(2''R'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2''S'',3''R'',4''R'',5''R'',6''S'')-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxan-3-yl (2''E'')-3-(3,4-dihydroxyphenyl)prop-2-enoate | OtherNames = <!-- <br> --> |Section1={{Chembox Identifiers | CASNo = 82854-37-3 | CASNo_Ref = {{cascite|correct|??}} | CASNoOther = | UNII_Ref = {{fdacite|correct|FDA}} | UNII = I04O1DT48T | PubChem = 5281771 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 4445084 | 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 | 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 | InChIKey = FSBUXLDOLNLABB-ISAKITKMBV | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = FSBUXLDOLNLABB-ISAKITKMSA-N
| MeSHName = }} |Section2={{Chembox Properties | Formula = C<sub>35</sub>H<sub>46</sub>O<sub>20</sub> | MolarMass = 786,73 g/mol | Appearance = | Density = | MeltingPtC = 200 to 220 | MeltingPt_notes = | BoilingPt = | Solubility = }} }} '''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.<ref>{{cite journal|title=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 |journal=Arkivoc |volume=2010 |issue=11 |pages=1–12 |doi=10.3998/ark.5550190.0011.b01|year=2010|doi-access=free |last1=Bernaś |first1=Urszula |last2=Hajmowicz |first2=Halina |last3=Madura |first3=Izabela D. |last4=Majcher |first4=Monika |last5=Synoradzki |first5=Ludwik |last6=Zawada |first6=Krzysztof |hdl=2027/spo.5550190.0011.b01 |hdl-access=free }}</ref> 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''.<ref>{{Cite journal | last1 = Stoll | first1 = A. | last2 = Renz | first2 = J. | last3 = Brack | first3 = A. | title = Isolierung und Konstitution des Echinacosids, eines Glykosids aus den Wurzeln von Echinacea angustifolia D. C. 6. Mitteilung über antibakterielle Stoffe | doi = 10.1002/hlca.19500330657 | journal = Helvetica Chimica Acta | volume = 33 | issue = 6| pages = 1877–1893 | year = 1950 }}</ref> <!-- ==Metabolism== -->
== References == {{reflist}}
{{Hydroxycinnamic acid}}
Category:Phenylpropanoid glycosides Category:Phenylethanoids
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