methyl (2S,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

• ChemBase ID: 154684
• Molecular Formular: C25H32O13
• Molecular Mass: 540.51378
• Monoisotopic Mass: 540.18429108
• SMILES: C/C=C\1/[C@@H](C(=CO[C@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)C(=O)OC)CC(=O)OCCc1ccc(c(c1)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@H](/C/2=C/C)CC(=O)OCCc2ccc(c(c2)O)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3/t14-,18+,20+,21-,22+,24-,25-/m0/s1
• InChIKey: RFWGABANNQMHMZ-HYYSZPHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate
• IUPAC Traditional name: methyl (4S,6S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethylidene-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate
• Synonyms: (2S,3E,4S)-3-Ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4-acetic acid 2-(3,4-dihydroxyphenyl)ethyl ester; Oleuropein

Database IDs

• CAS Number: 32619-42-4
• EC Number: 251-129-6
• MDL Number: MFCD16879008
• PubChem SID: 162248822
• PubChem CID: 6325757

CALCULATED PROPERTIES

• Acid pKa: 4.9403014
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -0.54729754
• LogD (pH = 7.4): -1.9990757
• Log P: 0.111275755
• Molar Refractivity: 128.2182 cm^3
• Polarizability: 50.971825 Å^3
• Polar Surface Area: 201.67 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Product Information

• Purity: ≥98.0%; ≥98.0% (HPLC)
• Grade: analytical standard
• Impurities: ≤5.0% water
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C25H32O13

DETAILS

Sigma Aldrich - 12247

Biochem/physiol Actions
Oleuropein has been shown to augment the secretion of noradrenaline and adrenaline in rat. 1
The primary phenolic compound found in olives and olive oil. Oleuropein hydrolyzes to form hydroxytyrosol and tyrosol, with hydroxytyrosol considered the main component associated with olive′s health benefits. Olive oil phenols demonstrate antioxidant, anti-thrombotic, anti-inflammatory and anti-atherogenic characteristics.