(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]oxy}methyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

• ChemBase ID: 154648
• Molecular Formular: C35H46O20
• Molecular Mass: 786.72774
• Monoisotopic Mass: 786.25824387
• SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H](O[C@@H]([C@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)OCCc1ccc(c(c1)O)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OCCc3ccc(c(c3)O)O)[C@@H]([C@H]([C@@H]2OC(=O)/C=C/c2ccc(c(c2)O)O)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
• 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/t14-,21+,22+,24-,25+,26+,27-,28+,29+,30+,31+,32+,33+,34+,35-/m0/s1
• InChIKey: FSBUXLDOLNLABB-WZJPPVJYSA-N

NAMES AND DATABASE IDS

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]oxy}methyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate
• IUPAC Traditional 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]oxy}methyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate
• Synonyms: Echinacoside

Database IDs

• CAS Number: 82854-37-3
• MDL Number: MFCD00075695
• Beilstein Number: 4778612
• PubChem SID: 162248786
• PubChem CID: 5281771

CALCULATED PROPERTIES

• Acid pKa: 9.010035
• H Acceptors: 19
• H Donor: 12
• LogD (pH = 5.5): -0.9515436
• LogD (pH = 7.4): -0.96193165
• Log P: -0.9514103
• Molar Refractivity: 180.8164 cm^3
• Polarizability: 72.69638 Å^3
• Polar Surface Area: 324.44 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: LZ5786500
• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); 98% (HPLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C35H46O20

DETAILS

Sigma Aldrich - 07668

Biochem/physiol Actions
Caffeic acid glycoside found in herbal medicine. Potential therapeutic for Parkinson′s disease.
Echinacoside was shown to promote proliferation of intestinal epithelial cells by increasing TGF-β1 expression.

Sigma Aldrich - 07538

Biochem/physiol Actions
Caffeic acid glycoside found in herbal medicine. Potential therapeutic for Parkinson′s disease.