[(2R,3R,4R)-3,4,5-trihydroxy-4-[(3,4,5-trihydroxybenzoyloxy)methyl]oxolan-2-yl]methyl 3,4,5-trihydroxybenzoate

• ChemBase ID: 157297
• Molecular Formular: C20H20O14
• Molecular Mass: 484.3644
• Monoisotopic Mass: 484.08530532
• SMILES: c1c(cc(c(c1O)O)O)C(=O)OC[C@@H]1[C@H]([C@@](C(O1)O)(COC(=O)c1cc(c(c(c1)O)O)O)O)O
• Canonical SMILES: O=C(c1cc(O)c(c(c1)O)O)OC[C@H]1OC([C@@]([C@@H]1O)(O)COC(=O)c1cc(O)c(c(c1)O)O)O
• InChI: InChI=1S/C20H20O14/c21-9-1-7(2-10(22)14(9)25)17(28)32-5-13-16(27)20(31,19(30)34-13)6-33-18(29)8-3-11(23)15(26)12(24)4-8/h1-4,13,16,19,21-27,30-31H,5-6H2/t13-,16-,19?,20-/m1/s1
• InChIKey: FEPAFOYQTIEEIS-IZUGRSKYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R)-3,4,5-trihydroxy-4-[(3,4,5-trihydroxybenzoyloxy)methyl]oxolan-2-yl]methyl 3,4,5-trihydroxybenzoate
• IUPAC Traditional name: [(2R,3R,4R)-3,4,5-trihydroxy-4-[(3,4,5-trihydroxybenzoyloxy)methyl]oxolan-2-yl]methyl 3,4,5-trihydroxybenzoate
• Synonyms: 2-C-(Hydroxymethyl)-D-ribofuranose 2′,5-digallate; Hamamelofuranose 2′,5-digallate; Hamamelitannin

Database IDs

• CAS Number: 469-32-9
• EC Number: 207-416-3
• MDL Number: MFCD00017418
• PubChem SID: 24845763; 162251434
• PubChem CID: 16211077

CALCULATED PROPERTIES

• Acid pKa: 7.8063464
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): 0.09854523
• LogD (pH = 7.4): -0.053568732
• Log P: 0.100670196
• Molar Refractivity: 107.6722 cm^3
• Polarizability: 42.10978 Å^3
• Polar Surface Area: 243.9 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C20H20O14

DETAILS

Sigma Aldrich - 04646

Application
Hamamelitannin can be used to study chromatography, aromatics, esters, hamamelis, heterocyclics, natural compounds, phenols, phytopharma standards, polyhydroxy compounds and tannins. Hamamelitannin significantly reduces biofilm metabolic activity of the following bacteria: Staphylococcus epidermidis, Staphylococcus aureus, Acinetobacter baumannii and Candida albicans strains. Hamamelitannin displays specific cytotoxic activity against colon cancer cells. Hamamelitannin has been used in a study to determine that quorum sensing inhibitors increase the success of antibiotic treatment by increasing the susceptibility of bacterial biofilms and/or by increasing host survival following infection.