2450-53-5 | 3,5-Di-O-caffeoylquinic acid

Packsize	Purity	Availability	Price	Discounted Price
1mg	95%	in stock	$47.00	$33.00
5mg	95%	in stock	$102.00	$72.00
50mg	95%	in stock	$162.00	$113.00
100mg	95%	in stock	$255.00	$178.00
250mg	95%	in stock	$455.00	$318.00
1g	95%	in stock	$1,162.00	$813.00

Description

• Catalog Number: AB52232
• Chemical Name: 3,5-Di-O-caffeoylquinic acid
• CAS Number: 2450-53-5
• Molecular Formula: C25H24O12
• Molecular Weight: 516.4509
• MDL Number: MFCD00951290
• SMILES: O=C(O[C@@H]1C[C@@](O)(C[C@H]([C@H]1O)OC(=O)/C=C/c1ccc(c(c1)O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O

Computed Properties

• Complexity: 825
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 2
• Defined Bond Stereocenter Count: 2
• Heavy Atom Count: 37
• Hydrogen Bond Acceptor Count: 12
• Hydrogen Bond Donor Count: 7
• Rotatable Bond Count: 9
• XLogP3: 1.5

Literature

• Incorporation of Privileged Structures into Bevirimat Can Improve Activity against Wild-Type and Bevirimat-Resistant HIV-1.

  Journal of medicinal chemistry 20161013

• 3,5-Dicaffeoylquinic acid isolated from Artemisia argyi and its ester derivatives exert anti-leucyl-tRNA synthetase of Giardia lamblia (GlLeuRS) and potential anti-giardial effects.

  Fitoterapia 20121001

• Protective effects of caffeoylquinic acids on the aggregation and neurotoxicity of the 42-residue amyloid β-protein.

  Bioorganic & medicinal chemistry 20121001

• Metabolomic profiling of the flower bud and rachis of Tussilago farfara with antitussive and expectorant effects on mice.

  Journal of ethnopharmacology 20120306

• Antioxidant activity-guided phytochemical investigation of Artemisia gmelinii Webb. ex Stechm.: isolation and spectroscopic challenges of 3,5-O-dicaffeoyl (epi?) quinic acid and its ethyl ester.

  Journal of pharmaceutical and biomedical analysis 20120205

• Design, synthesis and evaluation of caffeic acid phenethyl ester-based inhibitors targeting a selectivity pocket in the active site of human aldo-keto reductase 1B10.

  European journal of medicinal chemistry 20120201

• Dicaffeoylquinic acids in Yerba mate (Ilex paraguariensis St. Hilaire) inhibit NF-κB nucleus translocation in macrophages and induce apoptosis by activating caspases-8 and -3 in human colon cancer cells.

  Molecular nutrition & food research 20111001

• Youngia denticulata protects against oxidative damage induced by tert-butylhydroperoxide in HepG2 cells.

  Journal of medicinal food 20111001

• Phenolic substances from Phagnalon rupestre protect against 2,4,6-trinitrochlorobenzene-induced contact hypersensitivity.

  Journal of natural products 20110527

• Natural products from Scorzonera aristata (Asteraceae).

  Natural product communications 20100501

• Synthesis, anti-HIV and anti-oxidant activities of caffeoyl 5,6-anhydroquinic acid derivatives.

  Bioorganic & medicinal chemistry 20100115

• Preparative separation of isomeric caffeoylquinic acids from Flos Lonicerae by pH-zone-refining counter-current chromatography.

  Journal of chromatography. A 20081128

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

  Bioorganic & medicinal chemistry letters 20080815

• Simultaneous determination of 13 bioactive compounds in Herba Artemisiae Scopariae (Yin Chen) from different harvest seasons by HPLC-DAD.

  Journal of pharmaceutical and biomedical analysis 20080805

• In vitro hepatoprotective compounds from Suaeda glauca.

  Archives of pharmacal research 20080501

• Effects of plant alkylphenols on cytokine production, tyrosine nitration and inflammatory damage in the efferent phase of contact hypersensitivity.

  British journal of pharmacology 20071001

• Targeted natural product isolation guided by HPLC-SPE-NMR: constituents of Hubertia species.

  Journal of natural products 20070901

• Prevention of lipopolysaccharide-induced injury by 3,5-dicaffeoylquinic acid in endothelial cells.

  Acta pharmacologica Sinica 20070801

• Preparative isolation and purification of dicaffeoylquinic acids from the Ainsliaea fragrans champ by high-speed counter-current chromatography.

  Phytochemical analysis : PCA 20070101

• Determination of active constituents in Lonicera confusa DC. by capillary electrophoresis with amperometric detection.

  Biomedical chromatography : BMC 20061101

• Antiviral activities of purified compounds from Youngia japonica (L.) DC (Asteraceae, Compositae).

  Journal of ethnopharmacology 20060630

• Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus.

  Journal of natural products 20060401

• A novel inhibitor of respiratory syncytial virus isolated from ethnobotanicals.

  Antiviral research 20051201

• Neuroprotective effects of 3,5-dicaffeoylquinic acid on hydrogen peroxide-induced cell death in SH-SY5Y cells.

  Phytotherapy research : PTR 20050301

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

  Current medicinal chemistry 20050101

• (-)-3,5-Dicaffeoyl-muco-quinic acid isolated from Aster scaber contributes to the differentiation of PC12 cells: through tyrosine kinase cascade signaling.

  Biochemical and biophysical research communications 20040123

• Caffeic acid derivatives in the roots of yacon (Smallanthus sonchifolius).

  Journal of agricultural and food chemistry 20030129

• Identification of isomeric dicaffeoylquinic acids from Eleutherococcus senticosus using HPLC-ESI/TOF/MS and 1H-NMR methods.

  Phytochemical analysis : PCA 20020101

• A new caffeoyl quinic acid from aster scaber and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase.

  Chemical & pharmaceutical bulletin 20001101

• 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

• 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

• Differential inhibition of reverse transcriptase and cellular DNA polymerase-alpha activities by lignans isolated from Chinese herbs, Phyllanthus myrtifolius Moon, and tannins from Lonicera japonica Thunb and Castanopsis hystrix.

  Antiviral research 19950801