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6537-80-0,MFCD00189418
Catalog No.:AA003999

6537-80-0 | Cichoric Acid

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5mg
98% by HPLC
in stock  
$186.00   $130.00
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10mg
98% by HPLC
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$270.00   $189.00
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25mg
98% by HPLC
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$500.00   $350.00
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50mg
98% by HPLC
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$808.00   $565.00
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100mg
98% by HPLC
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$1,350.00   $945.00
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500mg
98% by HPLC
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$4,218.00   $2,952.00
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1000mg
98% by HPLC
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003999
Chemical Name:
Cichoric Acid
CAS Number:
6537-80-0
Molecular Formula:
C22H18O12
Molecular Weight:
474.3711
MDL Number:
MFCD00189418
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
NSC Number:
699173
Properties
Computed Properties
 
Complexity:
740  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
34  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
6  
Rotatable Bond Count:
11  
XLogP3:
2  

Upstream Synthesis Route

[1]HelveticaChimicaActa,2002,vol.85,#8,p.2328-2334

[1]HelveticaChimicaActa,2002,vol.85,#8,p.2328-2334

[1]HelveticaChimicaActa,2002,vol.85,#8,p.2328-2334

[1]HelveticaChimicaActa,2002,vol.85,#8,p.2328-2334

[1]HelveticaChimicaActa,2002,vol.85,#8,p.2328-2334

Downstream Synthesis Route

[1]Tetrahedron,1958,vol.4,p.43,44,45

[1]Tetrahedron,1958,vol.4,p.43,44,45

(2S,3S)-2,3-Bis-(E)-3-(3,4-diacetoxy-phenyl)-acryloyloxy-succinicacid 
  6537-80-0 

[1]SyntheticCommunications,1998,vol.28,p.737-740

[1]HelveticaChimicaActa,2002,vol.85,p.2328-2334

[1]HelveticaChimicaActa,2002,vol.85,p.2328-2334

Literature

Title: Chicoric acid is an antioxidant molecule that stimulates AMP kinase pathway in L6 myotubes and extends lifespan in Caenorhabditis elegans.

Journal: PloS one 20130101

Title: Cytotoxic effects of Echinacea purpurea flower extracts and cichoric acid on human colon cancer cells through induction of apoptosis.

Journal: Journal of ethnopharmacology 20121011

Title: Hydrolysis of chicoric and caftaric acids with esterases and Lactobacillus johnsonii in Vitro and in a gastrointestinal model.

Journal: Journal of agricultural and food chemistry 20120912

Title: Molecular dynamics approach to probe the allosteric inhibition of PTP1B by chlorogenic and cichoric acid.

Journal: Journal of chemical information and modeling 20120827

Title: Chicoric acid regulates behavioral and biochemical alterations induced by chronic stress in experimental Swiss albino mice.

Journal: Pharmacology, biochemistry, and behavior 20110901

Title: Inhibition of stromelysin-1 by caffeic acid derivatives from a propolis sample from Algeria.

Journal: Planta medica 20110701

Title: 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.

Journal: European journal of pharmacology 20110625

Title: Augmentation of immune response by chicoric acid through the modulation of CD28/CTLA-4 and Th1 pathway in chronically stressed mice.

Journal: Neuropharmacology 20110501

Title: Taraxacum officinale Weber extracts inhibit LPS-induced oxidative stress and nitric oxide production via the NF-κB modulation in RAW 264.7 cells.

Journal: Journal of ethnopharmacology 20110127

Title: 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.

Journal: Phytochemical analysis : PCA 20110101

Title: Computational fluid dynamics modeling of mass-transfer behavior in a bioreactor for hairy root culture. II. Analysis of ultrasound-intensified process.

Journal: Biotechnology progress 20110101

Title: 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: Journal of AOAC International 20110101

Title: 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: Journal of medicinal chemistry 20101125

Title: Effect of high pressure pasteurization on bacterial load and bioactivity of Echinacea purpurea.

Journal: Journal of food science 20100901

Title: New 2-arylnaphthalenediols and triol inhibitors of HIV-1 integrase--discovery of a new polyhydroxylated antiviral agent.

Journal: Bioorganic & medicinal chemistry 20100715

Title: Botulinum neurotoxin A protease: discovery of natural product exosite inhibitors.

Journal: Journal of the American Chemical Society 20100310

Title: Environmental stresses induce health-promoting phytochemicals in lettuce.

Journal: Plant physiology and biochemistry : PPB 20090701

Title: Natural product inhibitors of protein-protein interactions mediated by Src-family SH2 domains.

Journal: Bioorganic & medicinal chemistry letters 20090615

Title: Chicoric acid, a new compound able to enhance insulin release and glucose uptake.

Journal: Biochemical and biophysical research communications 20081205

Title: The total synthesis of fukiic acid, an HIV-1 integrase inhibitor.

Journal: European journal of medicinal chemistry 20081001

Title: Synthesis and antiviral properties of some polyphenols related to Salvia genus.

Journal: Bioorganic & medicinal chemistry letters 20080815

Title: Echinacea alkylamides modulate induced immune responses in T-cells.

Journal: Fitoterapia 20080101

Title: Genomics and proteomics of immune modulatory effects of a butanol fraction of echinacea purpurea in human dendritic cells.

Journal: BMC genomics 20080101

Title: Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of L-chicoric acid, as new HIV-1 integrase inhibitors.

Journal: European journal of medicinal chemistry 20071001

Title: Large-scale cultivation of adventitious roots of Echinacea purpurea in airlift bioreactors for the production of chichoric acid, chlorogenic acid and caftaric acid.

Journal: Biotechnology letters 20070801

Title: Design, synthesis, and biological evaluation of chicoric acid analogs as inhibitors of HIV-1 integrase.

Journal: Bioorganic & medicinal chemistry 20060701

Title: Genetic diversity in seed populations of Echinacea purpurea controls the capacity for regeneration, route of morphogenesis and phytochemical composition.

Journal: Plant cell reports 20060601

Title: Anti-human immunodeficiency virus activity of 3,4,5-tricaffeoylquinic acid in cultured cells of lettuce leaves.

Journal: Molecular nutrition & food research 20060401

Title: Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus.

Journal: Journal of natural products 20060401

Title: Preparative separation of cichoric acid from Echinacea purpurea by pH-zone-refining counter-current chromatography.

Journal: Journal of chromatography. A 20060120

Title: 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: Journal of AOAC International 20060101

Title: Synergistic antioxidative effects of alkamides, caffeic acid derivatives, and polysaccharide fractions from Echinacea purpurea on in vitro oxidation of human low-density lipoproteins.

Journal: Journal of agricultural and food chemistry 20051130

Title: Human gene expression as a tool to determine horticultural maturity in a bioactive plant (Echinacea purpurea L. Moench).

Journal: Journal of agricultural and food chemistry 20051019

Title: Synthesis and biological evaluation of geminal disulfones as HIV-1 integrase inhibitors.

Journal: Journal of medicinal chemistry 20050714

Title: Anti-HIV activities of natural antioxidant caffeic acid derivatives: toward an antiviral supplementation diet.

Journal: Current medicinal chemistry 20050101

Title: [Technology of extract improving the immune system].

Journal: Medicina (Kaunas, Lithuania) 20050101

Title: Profile of resistance of human immunodeficiency virus to mannose-specific plant lectins.

Journal: Journal of virology 20041001

Title: 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.

Journal: Virology 20040901

Title: HIV-1 integrase inhibitors: a decade of research and two drugs in clinical trial.

Journal: Current topics in medicinal chemistry 20040101

Title: Catechol-substituted L-chicoric acid analogues as HIV integrase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20031215

Title: HPLC method validated for the simultaneous analysis of cichoric acid and alkamides in Echinacea purpurea plants and products.

Journal: Journal of agricultural and food chemistry 20031119

Title: A new anti-HIV flavonoid glucuronide from Chrysanthemum morifolium.

Journal: Planta medica 20030901

Title: Caffeoyl naphthalenesulfonamide derivatives as HIV integrase inhibitors.

Journal: Bioorganic & medicinal chemistry 20030815

Title: Effect of drying temperature on alkylamide and cichoric acid concentrations of Echinacea purpurea.

Journal: Journal of agricultural and food chemistry 20030312

Title: Human immunodeficiency virus type-1 integrase containing a glycine to serine mutation at position 140 is attenuated for catalysis and resistant to integrase inhibitors.

Journal: Virology 20030201

Title: QSAR studies of HIV-1 integrase inhibition.

Journal: Bioorganic & medicinal chemistry 20021201

Title: Antiviral activity of characterized extracts from echinacea spp. (Heliantheae: Asteraceae) against herpes simplex virus (HSV-I).

Journal: Planta medica 20020901

Title: Dicaffeoyltartaric acid analogues inhibit human immunodeficiency virus type 1 (HIV-1) integrase and HIV-1 replication at nontoxic concentrations.

Journal: Journal of medicinal chemistry 20020815

Title: New class of HIV integrase inhibitors that block viral replication in cell culture.

Journal: Current biology : CB 20020723

Title: Stabilization of caffeic acid derivatives in Echinacea purpurea L. glycerin extract.

Journal: Journal of agricultural and food chemistry 20020703

Title: Phytochemical variation in echinacea from roots and flowerheads of wild and cultivated populations.

Journal: Journal of agricultural and food chemistry 20020619

Title: Simultaneous analysis of alkamides and caffeic acid derivatives for the identification of Echinacea purpurea, Echinacea angustifolia, Echinacea pallida and Parthenium integrifolium roots.

Journal: Planta medica 20020601

Title: [Determination of cichoric acid in Echinacea purpuea].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20020601

Title: Diketo acid inhibitor mechanism and HIV-1 integrase: implications for metal binding in the active site of phosphotransferase enzymes.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20020514

Title: HIV-1 integrase inhibitory phenylpropanoid glycosides from Clerodendron trichotomum.

Journal: Archives of pharmacal research 20010801

Title: Dicaffeoyl- or digalloyl pyrrolidine and furan derivatives as HIV integrase inhibitors.

Journal: Bioorganic & medicinal chemistry 20010601

Title: Predicting quantitative phytochemical markers in single Echinacea plants or clones from their DNA fingerprints.

Journal: Phytochemistry 20010301

Title: [Chicoric and chlorogenic acids in various plants growing in Georgia].

Journal: Prikladnaia biokhimiia i mikrobiologiia 20010101

Title: Viral entry as the primary target for the anti-HIV activity of chicoric acid and its tetra-acetyl esters.

Journal: Molecular pharmacology 20000901

Title: Synthesis and HIV-1 integrase inhibitory activities of caffeoylglucosides.

Journal: Bioorganic & medicinal chemistry letters 20000821

Title: Chicoric acid analogues as HIV-1 integrase inhibitors.

Journal: Journal of medicinal chemistry 19990422

Title: Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication.

Journal: Journal of medicinal chemistry 19990211

Title: 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: Journal of virology 19981001

Title: Human immunodeficiency virus type 1 cDNA integration: new aromatic hydroxylated inhibitors and studies of the inhibition mechanism.

Journal: Antimicrobial agents and chemotherapy 19980901

Title: 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).

Journal: Antiviral research 19980801

Title: Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase.

Journal: Antimicrobial agents and chemotherapy 19980101

Title: Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase.

Journal: Molecular pharmacology 19961001

Title: Inhibitors of HIV-1 replication [corrected; erratum to be published] that inhibit HIV integrase.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19960625

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Tags:6537-80-0 Molecular Formula|6537-80-0 MDL|6537-80-0 SMILES|6537-80-0 Cichoric Acid