(2R)-3-(3,4-dihydroxyphenyl)-2-[(3-{2-[2-(3,4-dihydroxyphenyl)ethenyl]-3,4-dihydroxyphenyl}prop-2-enoyl)oxy]propanoic acid hydrate

• ChemBase ID: 153250
• Molecular Formular: C26H24O11
• Molecular Mass: 512.46216
• Monoisotopic Mass: 512.13186159
• SMILES: c1cc(c(cc1C[C@H](C(=O)O)OC(=O)/C=C/c1ccc(c(c1/C=C/c1ccc(c(c1)O)O)O)O)O)O.O
• Canonical SMILES: O=C(O[C@@H](C(=O)O)Cc1ccc(c(c1)O)O)/C=C/c1ccc(c(c1/C=C/c1ccc(c(c1)O)O)O)O.O
• InChI: InChI=1S/C26H22O10.H2O/c27-18-7-2-14(11-21(18)30)1-6-17-16(4-9-20(29)25(17)33)5-10-24(32)36-23(26(34)35)13-15-3-8-19(28)22(31)12-15;/h1-12,23,27-31,33H,13H2,(H,34,35);1H2/t23-;/m1./s1
• InChIKey: XFUSRNNWIRPEDG-GNAFDRTKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-(3,4-dihydroxyphenyl)-2-[(3-{2-[2-(3,4-dihydroxyphenyl)ethenyl]-3,4-dihydroxyphenyl}prop-2-enoyl)oxy]propanoic acid hydrate
• IUPAC Traditional name: (2R)-3-(3,4-dihydroxyphenyl)-2-[(3-{2-[2-(3,4-dihydroxyphenyl)ethenyl]-3,4-dihydroxyphenyl}prop-2-enoyl)oxy]propanoic acid hydrate
• Synonyms: Dan phenolic acid A hydrate; Salvianolic acid A hydrate

Database IDs

• CAS Number: 96574-01-5(anhydrous)
• MDL Number: MFCD20527310
• PubChem SID: 162247389
• PubChem CID: 71311620

CALCULATED PROPERTIES

• Acid pKa: 3.1444283
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): 2.4072785
• LogD (pH = 7.4): 1.2629946
• Log P: 4.736837
• Molar Refractivity: 130.3667 cm^3
• Polarizability: 48.977795 Å^3
• Polar Surface Area: 184.98 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: ≥19 mg/mL
• Apperance: yellow powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C26H22O10 · xH2O

DETAILS

Sigma Aldrich - SML0045

Biochem/physiol Actions
Salvianolic acid A is cell protective antioxidant originally isolated from Salvia. It has been found to attenuate PDGF-induced ROS formation in hepatic stellate cells and protected against isoproterenol-induced myocardial damage in rats.