4,5-Dicaffeoylquinic Acid

4,5-Dicaffeoylquinic acid (4,5-DCQA) is a polyphenol originally isolated from G. fagetorum and G. pseudomollugo that has diverse biological activities, including anti-HIV replication, antioxidative, anti-inflammatory, and anti-melanogenic properties. It inhibits HIV-1 integrase 3' end processing, 3' end joining, and disintegration with IC50 values of 0.13, 0.24, and 0.3 µg/ml, respectively. It also inhibits HIV-1 replication in MT-2 T lymphoblastoid cells with an EC50 value of 2 µg/ml. 4,5-DCQA scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH, Cay-14805) radicals in a cell-free assay (IC50 = 19.8 µM) and inhibits superoxide production in human neutrophils activated by N-formyl-Met-Leu-Phe (fMLF, Cay-21495) and cytochalasin B (Cay-11328, IC50 = 1.49 µM). It decreases prostaglandin E2 (PGE2, Cay-14010) production in LPS-stimulated U937 cells when used at concentrations of 5 and 10 µg/ml but increases it when used at 200 µg/ml and increases production of TNF-alpha at concentrations ranging from 5 to 200 µg/ml. It inhibits the synthesis of MCP3 in U937 cells. 4,5-DCQA (25 µM) inhibits melanogenesis by 84% and decreases the levels of proteins involved in melanin biosynthesis, including tyrosinase, TRP-1, DCT, and MITF in B16F1 murine melanocytes.Formal Name: (1R,3R,4S,5R)-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,5-dihydroxy-cyclohexanecarboxylic acid. CAS Number: 57378-72-0. Synonyms: 4,5-DCQA, Isochlorogenic Acid C. Molecular Formula: C25H24O12. Formula Weight: 516.5. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: DMF: 30 mg/ml, DMF:PBS (pH 7.2) (1:5): 0.16 mg/ml, DMSO: 5 mg/ml. lambdamax: 219, 245, 331 nm. SMILES: O=C(/C=C/C1=CC=C(O)C(O)=C1)O[C@H]2[C@@H](OC(/C=C/C3=CC=C(O)C(O)=C3)=O)[C@H](O)C[C@@](C(O)=O)(O)C2. InChi Code: InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1. InChi Key: UFCLZKMFXSILNL-RVXRWRFUSA-N. Origin: Plant/Lonicera japonica Thunb..