4,5-Dicaffeoylquinic Acid

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Cat No: 27892

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.{...

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Territorial Availability: Available through Bertin Technologies only in France

Synonyms:

(1R,3R,4S,5R)-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,5-dihydroxy-cyclohexanecarboxylic acid

Correlated keywords:

32451-88-0 Galium antiHIV oxidative antiinflammatory antimelanogenic HIV1 MT2 PGE 2 lipopolysaccharide U 937 TNF? MCP 3 TRP1 B 16F1 16F 1 B16F B16

Product Overview:
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.{48456,36685,43194,48457,47056} 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.{43194} 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).{36685} 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.{48457} 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.{47056}

Size	5 mg
Shipping	dry ice
CAS Number	57378-72-0
Molecular Formula	C₂₅H₂₄O₁₂
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
Molecular Weight	516,5
Formulation	A solid
Purity	≥98%
Custom Code	2907.29
UNSPSC code	12352100

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Cayman Chemical's mission is to help make research possible by supplying scientists worldwide with the basic research tools necessary for advancing human and animal health. Our utmost commitment to healthcare researchers is to offer the highest quality products with an affordable pricing policy.

Our scientists are experts in the synthesis, purification, and characterization of biochemicals ranging from small drug-like heterocycles to complex biolipids, fatty acids, and many others. We are also highly skilled in all aspects of assay and antibody development, protein expression, crystallization, and structure determination.

Over the past thirty years, Cayman developed a deep knowledge base in lipid biochemistry, including research involving the arachidonic acid cascade, inositol phosphates, and cannabinoids. This knowledge enabled the production of reagents of exceptional quality for cancer, oxidative injury, epigenetics, neuroscience, inflammation, metabolism, and many additional lines of research.

Our organic and analytical chemists specialize in the rapid development of manufacturing processes and analytical methods to carry out clinical and commercial GMP-API production. Pre-clinical drug discovery efforts are currently underway in the areas of bone restoration and repair, muscular dystrophy, oncology, and inflammation. A separate group of Ph.D.-level scientists are dedicated to offering Hit-to-Lead Discovery and Profiling Services for epigenetic targets. Our knowledgeable chemists can be contracted to perform complete sample analysis for analytes measured by the majority of our assays. We also offer a wide range of analytical services using LC-MS/MS, HPLC, GC, and many other techniques.

Accreditations
ISO/IEC 17025:2005
ISO Guide 34:2009

Cayman is a leader in the field of emerging drugs of abuse, providing high-purity Schedule I-V Controlled Substances to federally-licensed laboratories and qualified academic research institutions for forensic analyses. We are certified by ACLASS Accreditation Services with dual accreditation to ISO/IEC 17025:2005 and ISO Guide 34:2009.