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Cichoric Acid

CAS No.:
6537-80-0
Catalog Number:
AG0039C1
Molecular Formula:
C22H18O12
Molecular Weight:
474.3711
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
10mg
99%
1 week
United States
$157
- +
25mg
99%
1 week
United States
$257
- +
50mg
99%
1 week
United States
$407
- +
Product Description
Catalog Number:
AG0039C1
Chemical Name:
Cichoric Acid
CAS Number:
6537-80-0
Molecular Formula:
C22H18O12
Molecular Weight:
474.3711
MDL Number:
MFCD00189418
IUPAC Name:
(2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
InChI:
InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1
InChI Key:
YDDGKXBLOXEEMN-IABMMNSOSA-N
SMILES:
O=C(O[C@H]([C@H](C(=O)O)OC(=O)/C=C/c1ccc(c(c1)O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
EC Number:
615-177-5
UNII:
S4YY3V8YHD
NSC Number:
699173
Properties
Complexity:
740  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
2  
Exact Mass:
474.08g/mol
Formal Charge:
0
Heavy Atom Count:
34  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
6  
Isotope Atom Count:
0
Molecular Weight:
474.374g/mol
Monoisotopic Mass:
474.08g/mol
Rotatable Bond Count:
11  
Topological Polar Surface Area:
208A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2  
Literature
Title Journal
Chicoric acid is an antioxidant molecule that stimulates AMP kinase pathway in L6 myotubes and extends lifespan in Caenorhabditis elegans. PloS one 20130101
Cytotoxic effects of Echinacea purpurea flower extracts and cichoric acid on human colon cancer cells through induction of apoptosis. Journal of ethnopharmacology 20121011
Hydrolysis of chicoric and caftaric acids with esterases and Lactobacillus johnsonii in Vitro and in a gastrointestinal model. Journal of agricultural and food chemistry 20120912
Molecular dynamics approach to probe the allosteric inhibition of PTP1B by chlorogenic and cichoric acid. Journal of chemical information and modeling 20120827
Chicoric acid regulates behavioral and biochemical alterations induced by chronic stress in experimental Swiss albino mice. Pharmacology, biochemistry, and behavior 20110901
Inhibition of stromelysin-1 by caffeic acid derivatives from a propolis sample from Algeria. Planta medica 20110701
Luteolin and chicoric acid synergistically inhibited inflammatory responses via inactivation of PI3K-Akt pathway and impairment of NF-κB translocation in LPS stimulated RAW 264.7 cells. European journal of pharmacology 20110625
Augmentation of immune response by chicoric acid through the modulation of CD28/CTLA-4 and Th1 pathway in chronically stressed mice. Neuropharmacology 20110501
Taraxacum officinale Weber extracts inhibit LPS-induced oxidative stress and nitric oxide production via the NF-κB modulation in RAW 264.7 cells. Journal of ethnopharmacology 20110127
Analysis of eleven phenolic compounds including novel p-coumaroyl derivatives in lettuce (Lactuca sativa L.) by ultra-high-performance liquid chromatography with photodiode array and mass spectrometry detection. Phytochemical analysis : PCA 20110101
Computational fluid dynamics modeling of mass-transfer behavior in a bioreactor for hairy root culture. II. Analysis of ultrasound-intensified process. Biotechnology progress 20110101
Determination of major phenolic compounds in Echinacea spp. raw materials and finished products by high-performance liquid chromatography with ultraviolet detection: single-laboratory validation matrix extension. Journal of AOAC International 20110101
Design, synthesis, and biological evaluation of novel hybrid dicaffeoyltartaric/diketo acid and tetrazole-substituted L-chicoric acid analogue inhibitors of human immunodeficiency virus type 1 integrase. Journal of medicinal chemistry 20101125
Effect of high pressure pasteurization on bacterial load and bioactivity of Echinacea purpurea. Journal of food science 20100901
New 2-arylnaphthalenediols and triol inhibitors of HIV-1 integrase--discovery of a new polyhydroxylated antiviral agent. Bioorganic & medicinal chemistry 20100715
Botulinum neurotoxin A protease: discovery of natural product exosite inhibitors. Journal of the American Chemical Society 20100310
Environmental stresses induce health-promoting phytochemicals in lettuce. Plant physiology and biochemistry : PPB 20090701
Natural product inhibitors of protein-protein interactions mediated by Src-family SH2 domains. Bioorganic & medicinal chemistry letters 20090615
Chicoric acid, a new compound able to enhance insulin release and glucose uptake. Biochemical and biophysical research communications 20081205
The total synthesis of fukiic acid, an HIV-1 integrase inhibitor. European journal of medicinal chemistry 20081001
Synthesis and antiviral properties of some polyphenols related to Salvia genus. Bioorganic & medicinal chemistry letters 20080815
Echinacea alkylamides modulate induced immune responses in T-cells. Fitoterapia 20080101
Genomics and proteomics of immune modulatory effects of a butanol fraction of echinacea purpurea in human dendritic cells. BMC genomics 20080101
Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of L-chicoric acid, as new HIV-1 integrase inhibitors. European journal of medicinal chemistry 20071001
Large-scale cultivation of adventitious roots of Echinacea purpurea in airlift bioreactors for the production of chichoric acid, chlorogenic acid and caftaric acid. Biotechnology letters 20070801
Design, synthesis, and biological evaluation of chicoric acid analogs as inhibitors of HIV-1 integrase. Bioorganic & medicinal chemistry 20060701
Genetic diversity in seed populations of Echinacea purpurea controls the capacity for regeneration, route of morphogenesis and phytochemical composition. Plant cell reports 20060601
Anti-human immunodeficiency virus activity of 3,4,5-tricaffeoylquinic acid in cultured cells of lettuce leaves. Molecular nutrition & food research 20060401
Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus. Journal of natural products 20060401
Preparative separation of cichoric acid from Echinacea purpurea by pH-zone-refining counter-current chromatography. Journal of chromatography. A 20060120
Development and validation of a high-throughput based on liquid chromatography with ultraviolet absorption and mass spectrometry detection method for quantitation of cichoric acid in Echinacea purpurea aerial-based dietary supplements. Journal of AOAC International 20060101
Synergistic antioxidative effects of alkamides, caffeic acid derivatives, and polysaccharide fractions from Echinacea purpurea on in vitro oxidation of human low-density lipoproteins. Journal of agricultural and food chemistry 20051130
Human gene expression as a tool to determine horticultural maturity in a bioactive plant (Echinacea purpurea L. Moench). Journal of agricultural and food chemistry 20051019
Synthesis and biological evaluation of geminal disulfones as HIV-1 integrase inhibitors. Journal of medicinal chemistry 20050714
Anti-HIV activities of natural antioxidant caffeic acid derivatives: toward an antiviral supplementation diet. Current medicinal chemistry 20050101
[Technology of extract improving the immune system]. Medicina (Kaunas, Lithuania) 20050101
Profile of resistance of human immunodeficiency virus to mannose-specific plant lectins. Journal of virology 20041001
L-chicoric acid inhibits human immunodeficiency virus type 1 integration in vivo and is a noncompetitive but reversible inhibitor of HIV-1 integrase in vitro. Virology 20040901
HIV-1 integrase inhibitors: a decade of research and two drugs in clinical trial. Current topics in medicinal chemistry 20040101
Catechol-substituted L-chicoric acid analogues as HIV integrase inhibitors. Bioorganic & medicinal chemistry letters 20031215
HPLC method validated for the simultaneous analysis of cichoric acid and alkamides in Echinacea purpurea plants and products. Journal of agricultural and food chemistry 20031119
A new anti-HIV flavonoid glucuronide from Chrysanthemum morifolium. Planta medica 20030901
Caffeoyl naphthalenesulfonamide derivatives as HIV integrase inhibitors. Bioorganic & medicinal chemistry 20030815
Effect of drying temperature on alkylamide and cichoric acid concentrations of Echinacea purpurea. Journal of agricultural and food chemistry 20030312
Human immunodeficiency virus type-1 integrase containing a glycine to serine mutation at position 140 is attenuated for catalysis and resistant to integrase inhibitors. Virology 20030201
QSAR studies of HIV-1 integrase inhibition. Bioorganic & medicinal chemistry 20021201
Antiviral activity of characterized extracts from echinacea spp. (Heliantheae: Asteraceae) against herpes simplex virus (HSV-I). Planta medica 20020901
Dicaffeoyltartaric acid analogues inhibit human immunodeficiency virus type 1 (HIV-1) integrase and HIV-1 replication at nontoxic concentrations. Journal of medicinal chemistry 20020815
New class of HIV integrase inhibitors that block viral replication in cell culture. Current biology : CB 20020723
Stabilization of caffeic acid derivatives in Echinacea purpurea L. glycerin extract. Journal of agricultural and food chemistry 20020703
Phytochemical variation in echinacea from roots and flowerheads of wild and cultivated populations. Journal of agricultural and food chemistry 20020619
Simultaneous analysis of alkamides and caffeic acid derivatives for the identification of Echinacea purpurea, Echinacea angustifolia, Echinacea pallida and Parthenium integrifolium roots. Planta medica 20020601
[Determination of cichoric acid in Echinacea purpuea]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20020601
Diketo acid inhibitor mechanism and HIV-1 integrase: implications for metal binding in the active site of phosphotransferase enzymes. Proceedings of the National Academy of Sciences of the United States of America 20020514
HIV-1 integrase inhibitory phenylpropanoid glycosides from Clerodendron trichotomum. Archives of pharmacal research 20010801
Dicaffeoyl- or digalloyl pyrrolidine and furan derivatives as HIV integrase inhibitors. Bioorganic & medicinal chemistry 20010601
Predicting quantitative phytochemical markers in single Echinacea plants or clones from their DNA fingerprints. Phytochemistry 20010301
[Chicoric and chlorogenic acids in various plants growing in Georgia]. Prikladnaia biokhimiia i mikrobiologiia 20010101
Viral entry as the primary target for the anti-HIV activity of chicoric acid and its tetra-acetyl esters. Molecular pharmacology 20000901
Synthesis and HIV-1 integrase inhibitory activities of caffeoylglucosides. Bioorganic & medicinal chemistry letters 20000821
Chicoric acid analogues as HIV-1 integrase inhibitors. Journal of medicinal chemistry 19990422
Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication. Journal of medicinal chemistry 19990211
Resistance to the anti-human immunodeficiency virus type 1 compound L-chicoric acid results from a single mutation at amino acid 140 of integrase. Journal of virology 19981001
Human immunodeficiency virus type 1 cDNA integration: new aromatic hydroxylated inhibitors and studies of the inhibition mechanism. Antimicrobial agents and chemotherapy 19980901
L-chicoric acid, an inhibitor of human immunodeficiency virus type 1 (HIV-1) integrase, improves on the in vitro anti-HIV-1 effect of Zidovudine plus a protease inhibitor (AG1350). Antiviral research 19980801
Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase. Antimicrobial agents and chemotherapy 19980101
Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase. Molecular pharmacology 19961001
Inhibitors of HIV-1 replication [corrected; erratum to be published] that inhibit HIV integrase. Proceedings of the National Academy of Sciences of the United States of America 19960625
Properties