methyl (2E)-4-(2-nitro-3-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)-4-oxobut-2-enoate

• ChemBase ID: 175527
• Molecular Formular: C25H27NO15
• Molecular Mass: 581.47958
• Monoisotopic Mass: 581.13806917
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)Oc1c(c(ccc1)C(=O)/C=C/C(=O)OC)[N+](=O)[O-])OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: COC(=O)/C=C/C(=O)c1cccc(c1[N+](=O)[O-])O[C@@H]1O[C@@H](COC(=O)C)[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C25H27NO15/c1-12(27)36-11-19-22(37-13(2)28)23(38-14(3)29)24(39-15(4)30)25(41-19)40-18-8-6-7-16(21(18)26(33)34)17(31)9-10-20(32)35-5/h6-10,19,22-25H,11H2,1-5H3/b10-9+/t19-,22-,23+,24-,25-/m1/s1
• InChIKey: GZEJVMGQFOJCDQ-WHIUSNHVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2E)-4-(2-nitro-3-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)-4-oxobut-2-enoate
• IUPAC Traditional name: methyl (2E)-4-(2-nitro-3-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)-4-oxobut-2-enoate
• Synonyms: (2E)-4-[2-Nitro-3-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]phenyl]-4-oxo-2-butenoic Acid Methyl Ester

Database IDs

• CAS Number: 224044-68-2
• PubChem SID: 164231437
• PubChem CID: 11801372

CALCULATED PROPERTIES

• Acid pKa: 11.935188
• H Acceptors: 10
• H Donor: 0
• LogD (pH = 5.5): 1.2254044
• LogD (pH = 7.4): 1.2253976
• Log P: 1.2254045
• Molar Refractivity: 131.2492 cm^3
• Polarizability: 51.968475 Å^3
• Polar Surface Area: 212.85 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane

DETAILS

Toronto Research Chemicals - N565090

Used in the preparation of human UV filters.

REFERENCES

• Manthey, M. et al.: J. Org. Chem. 64, 3930 (1999)