| Identification | Back Directory | [Name]
Isochlorogenic acid C | [CAS]
57378-72-0 | [Synonyms]
Isochlorogenic acid C
4,5-Dicaffeoylquinic acid
3,4-O-Dicaffeoylquinic acid
Isochlorogenic acid C(4,5')
4,5-Dicaffeoylquinic acid, >99%
Isochlorogenic acid C USP/EP/BP
1β,5α-Dihydroxy-3β,4β-bis[3-(3,4-dihydroxyphenyl)propenoyloxy]cyclohexanecarboxylic acid
(1R)-1,3β-Dihydroxy-4α,5α-bis[3-(3,4-dihydroxyphenyl)acryloyloxy]-1β-cyclohexanecarboxylic acid
(1R,3R,4S,5R)-3,4-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,5-dihydroxycyclohexanecarboxylic acid
(1R,3R,4S,5R)-1,5-Dihydroxy-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1-cyclohexanecarboxylicaci
(1R,3R,4S,5R)-1,5-Dihydroxy-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1-cyclohexanecarboxylic acid
Cyclohexanecarboxylic acid, 3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,5-dihydroxy-, (1R,3R,4S,5R)- | [Molecular Formula]
C25H24O12 | [MDL Number]
MFCD10566623 | [MOL File]
57378-72-0.mol | [Molecular Weight]
516.45 |
| Chemical Properties | Back Directory | [Boiling point ]
810.8±65.0 °C(Predicted) | [density ]
1?+-.0.1 g/cm3(Predicted) | [storage temp. ]
?20°C | [solubility ]
DMF: 30 mg/ml; DMF:PBS (pH 7.2) (1:5): 0.16 mg/ml; DMSO: 5 mg/ml | [form ]
A solid | [pka]
3.70±0.50(Predicted) |
| Hazard Information | Back Directory | [Description]
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.1,2,3,4,5 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.3 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; Item No. 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; Item No. 21495) and cytochalasin B (Item No. 11328; IC50 = 1.49 μM).2 It decreases prostaglandin E2 (PGE2; Item No. 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-α at concentrations ranging from 5 to 200 μg/ml.4 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.5 | [Uses]
4,5-Dicaffeoylquinic Acid is a selective inhibitor of human immunodeficiency virus type 1 integrase. | [Definition]
ChEBI: 4,5-di-O-caffeoylquinic acid is a quinic acid. |
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