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

• ChemBase ID: 157644
• Molecular Formular: C26H22O10
• Molecular Mass: 494.44688
• Monoisotopic Mass: 494.1212969
• 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
• 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
• InChI: InChI=1S/C26H22O10/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)/t23-/m1/s1
• InChIKey: YMGFTDKNIWPMGF-HSZRJFAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-{2-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-3,4-dihydroxyphenyl}prop-2-enoyl]oxy}propanoic acid; (2R)-3-(3,4-dihydroxyphenyl)-2-[(3-{2-[2-(3,4-dihydroxyphenyl)ethenyl]-3,4-dihydroxyphenyl}prop-2-enoyl)oxy]propanoic acid
• IUPAC Traditional name: salvianolic acid A; (2R)-3-(3,4-dihydroxyphenyl)-2-[(3-{2-[2-(3,4-dihydroxyphenyl)ethenyl]-3,4-dihydroxyphenyl}prop-2-enoyl)oxy]propanoic acid
• Synonyms: (+)-Salvianolic acid A; Dan Phenolic Acid A; Salvianolic Acid; Salvianolic Acid A; (αR)-α-[[(2E)-3-[2-[(1E)-2-(3,4-Dihydroxyphenyl)ethenyl]-3,4-dihydroxyphenyl]-1-oxo-2-propen-1-yl]oxy]-3,4-dihydroxybenzenepropanoic acid; Salvianolic acid A

Database IDs

• CAS Number: 96574-01-5
• MDL Number: MFCD08458447
• Beilstein Number: 2660108
• PubChem SID: 162251781
• PubChem CID: 5281793

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: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 164-167°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• 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): C26H22O10

DETAILS

Toronto Research Chemicals - S100800

ISalvianolic 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 h

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)