(2R)-2-[(2S,3S)-4-{3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carbonyloxy]-3-(3,4-dihydroxyphenyl)propanoic acid

• ChemBase ID: 157643
• Molecular Formular: C36H30O16
• Molecular Mass: 718.6138
• Monoisotopic Mass: 718.15338488
• SMILES: c1cc(c(cc1C[C@H](C(=O)O)OC(=O)/C=C/c1ccc(c2c1[C@@H]([C@H](O2)c1ccc(c(c1)O)O)C(=O)O[C@H](Cc1ccc(c(c1)O)O)C(=O)O)O)O)O
• Canonical SMILES: O=C(O[C@@H](C(=O)O)Cc1ccc(c(c1)O)O)/C=C/c1ccc(c2c1[C@H](C(=O)O[C@@H](C(=O)O)Cc1ccc(c(c1)O)O)[C@H](O2)c1ccc(c(c1)O)O)O
• InChI: InChI=1S/C36H30O16/c37-20-6-1-16(11-24(20)41)13-27(34(45)46)50-29(44)10-5-18-3-9-23(40)33-30(18)31(32(52-33)19-4-8-22(39)26(43)15-19)36(49)51-28(35(47)48)14-17-2-7-21(38)25(42)12-17/h1-12,15,27-28,31-32,37-43H,13-14H2,(H,45,46)(H,47,48)/t27-,28-,31+,32-/m1/s1
• InChIKey: SNKFFCBZYFGCQN-MZBUKOFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(2S,3S)-4-{3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carbonyloxy]-3-(3,4-dihydroxyphenyl)propanoic acid; (2R)-2-{[(2E)-3-[(2S,3S)-3-{[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid
• IUPAC Traditional name: (2R)-2-[(2S,3S)-4-{3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carbonyloxy]-3-(3,4-dihydroxyphenyl)propanoic acid; (2R)-2-{[(2E)-3-[(2S,3S)-3-{[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid
• Synonyms: Salvianolic acid B; (2S,3S)-4-[(1E)-3-[(1R)-1-Carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxo-1-propen-1-yl]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-7-hydroxy-3-benzofurancarboxylic acid 3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethyl] ester; (2S,3S)-4-[(1E)-3-[(1R)-1-Carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxo-1-propen-1-yl]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-7-hydroxy-3-benzofurancarboxylic Acid 3-[(1R)-1-Carboxy-2-(3,4-dihydroxyphenyl)ethyl]ester; Dan Shen Suan B; Danfensuan B; Lithospermic Acid B; Salvianolic Acid B

Database IDs

• CAS Number: 121521-90-2
• PubChem SID: 162251780
• PubChem CID: 6451084

CALCULATED PROPERTIES

• Acid pKa: 2.7735696
• H Acceptors: 14
• H Donor: 9
• LogD (pH = 5.5): 0.19945902
• LogD (pH = 7.4): -1.9595973
• Log P: 4.987508
• Molar Refractivity: 177.0009 cm^3
• Polarizability: 68.05364 Å^3
• Polar Surface Area: 278.04 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol
• Apperance: Oil; Yellow Solid
• Melting Point: 98-110°C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: DF6492107
• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (HPLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C36H30O16

DETAILS

Toronto Research Chemicals - S100820

Salvianolic acid A (Sal A) and salvianolic acid B (Sal B) were isolated and purified from the crude extract of Salvia miltiorrhiza. Antioxidant activities of Sal A and Sal B were also evaluated and the ABTS results showed that Sal A and Sal B exhibited hi

REFERENCES

• Lin, T., et al.: Biochem. Pharmacol., 51, 1237 (1996)
• Abd-Elazem, I., et al.: Antivir. Res., 55, 91 (1996)
• Ji, X., et al.: Life Sci., 73, 1413 (1996)
• Lin, Y., et al.: Biochem. Biophys. Res. Commun., 348, 593 (1996)