2450-53-5,MFCD00951290
Catalog No.:AA0039JG

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

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1mg
97%(HPLC)
in stock  
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5mg
≥95%
in stock  
$113.00   $79.00
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10mg
≥95%
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$202.00   $141.00
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25mg
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50mg
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA0039JG
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
Properties
Computed Properties
 
Complexity:
825  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
2  
Formal Charge:
0  
Heavy Atom Count:
37  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
7  
Isotope Atom Count:
0  
Rotatable Bond Count:
9  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
1.5  

Upstream Synthesis Route

[1]AgriculturalandBiologicalChemistry,1985,vol.49,#8,p.2467-2470

Literature

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

Journal: Journal of medicinal chemistry 20161013

Title: 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.

Journal: Fitoterapia 20121001

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

Journal: Bioorganic & medicinal chemistry 20121001

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

Journal: Journal of ethnopharmacology 20120306

Title: 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: Journal of pharmaceutical and biomedical analysis 20120205

Title: 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.

Journal: European journal of medicinal chemistry 20120201

Title: 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.

Journal: Molecular nutrition & food research 20111001

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

Journal: Journal of medicinal food 20111001

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

Journal: Journal of natural products 20110527

Title: Natural products from Scorzonera aristata (Asteraceae).

Journal: Natural product communications 20100501

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

Journal: Bioorganic & medicinal chemistry 20100115

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

Journal: Journal of chromatography. A 20081128

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

Journal: Bioorganic & medicinal chemistry letters 20080815

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

Journal: Journal of pharmaceutical and biomedical analysis 20080805

Title: In vitro hepatoprotective compounds from Suaeda glauca.

Journal: Archives of pharmacal research 20080501

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

Journal: British journal of pharmacology 20071001

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

Journal: Journal of natural products 20070901

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

Journal: Acta pharmacologica Sinica 20070801

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

Journal: Phytochemical analysis : PCA 20070101

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

Journal: Biomedical chromatography : BMC 20061101

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

Journal: Journal of ethnopharmacology 20060630

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

Journal: Journal of natural products 20060401

Title: A novel inhibitor of respiratory syncytial virus isolated from ethnobotanicals.

Journal: Antiviral research 20051201

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

Journal: Phytotherapy research : PTR 20050301

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

Journal: Current medicinal chemistry 20050101

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

Journal: Biochemical and biophysical research communications 20040123

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

Journal: Journal of agricultural and food chemistry 20030129

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

Journal: Phytochemical analysis : PCA 20020101

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

Journal: Chemical & pharmaceutical bulletin 20001101

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: 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

Title: 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.

Journal: Antiviral research 19950801

Title: Zhang YH, et al. 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. 2012 Oct;83(7):1281-5.

Title: Malarz J, et al. Long-term cultured hairy roots of chicory-a rich source of hydroxycinnamates and 8-deoxylactucin glucoside. Appl Biochem Biotechnol. 2013 Dec;171(7):1589-601.

Title: Wan C, et al. Isolation and identification of phenolic compounds from Gynura divaricata leaves. Pharmacogn Mag. 2011 Apr;7(26):101-8.

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Additional Info:
SDS
Historical Records
Tags:2450-53-5 Molecular Formula|2450-53-5 MDL|2450-53-5 SMILES|2450-53-5 3,5-Di-O-caffeoylquinic acid
Catalog No.: AA0039JG
2450-53-5,MFCD00951290
2450-53-5 | 3,5-Di-O-caffeoylquinic acid
Pack Size: 1mg
Purity: 97%(HPLC)
in stock
$47.00 $33.00
Pack Size: 5mg
Purity: ≥95%
in stock
$113.00 $79.00
Pack Size: 10mg
Purity: ≥95%
in stock
$202.00 $141.00
Pack Size: 25mg
Purity: ≥95%
in stock
$446.00 $312.00
Pack Size: 50mg
Purity: ≥95%
in stock
$669.00 $468.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA0039JG
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
Properties
Complexity: 825  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 2  
Defined Bond Stereocenter Count: 2  
Formal Charge: 0  
Heavy Atom Count: 37  
Hydrogen Bond Acceptor Count: 12  
Hydrogen Bond Donor Count: 7  
Isotope Atom Count: 0  
Rotatable Bond Count: 9  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 1.5  
Upstream Synthesis Route
1049703-62-9    331-39-5    77-95-2    2450-53-5 

[1]AgriculturalandBiologicalChemistry,1985,vol.49,#8,p.2467-2470

Literature fold

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

Journal: Journal of medicinal chemistry20161013

Title: 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.

Journal: Fitoterapia20121001

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

Journal: Bioorganic & medicinal chemistry20121001

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

Journal: Journal of ethnopharmacology20120306

Title: 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: Journal of pharmaceutical and biomedical analysis20120205

Title: 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.

Journal: European journal of medicinal chemistry20120201

Title: 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.

Journal: Molecular nutrition & food research20111001

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

Journal: Journal of medicinal food20111001

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

Journal: Journal of natural products20110527

Title: Natural products from Scorzonera aristata (Asteraceae).

Journal: Natural product communications20100501

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

Journal: Bioorganic & medicinal chemistry20100115

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

Journal: Journal of chromatography. A20081128

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

Journal: Bioorganic & medicinal chemistry letters20080815

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

Journal: Journal of pharmaceutical and biomedical analysis20080805

Title: In vitro hepatoprotective compounds from Suaeda glauca.

Journal: Archives of pharmacal research20080501

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

Journal: British journal of pharmacology20071001

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

Journal: Journal of natural products20070901

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

Journal: Acta pharmacologica Sinica20070801

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

Journal: Phytochemical analysis : PCA20070101

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

Journal: Biomedical chromatography : BMC20061101

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

Journal: Journal of ethnopharmacology20060630

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

Journal: Journal of natural products20060401

Title: A novel inhibitor of respiratory syncytial virus isolated from ethnobotanicals.

Journal: Antiviral research20051201

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

Journal: Phytotherapy research : PTR20050301

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

Journal: Current medicinal chemistry20050101

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

Journal: Biochemical and biophysical research communications20040123

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

Journal: Journal of agricultural and food chemistry20030129

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

Journal: Phytochemical analysis : PCA20020101

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

Journal: Chemical & pharmaceutical bulletin20001101

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 chemistry19990211

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

Journal: Antimicrobial agents and chemotherapy19980101

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

Journal: Molecular pharmacology19961001

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 America19960625

Title: 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.

Journal: Antiviral research19950801

Title: Zhang YH, et al. 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. 2012 Oct;83(7):1281-5.

Title: Malarz J, et al. Long-term cultured hairy roots of chicory-a rich source of hydroxycinnamates and 8-deoxylactucin glucoside. Appl Biochem Biotechnol. 2013 Dec;171(7):1589-601.

Title: Wan C, et al. Isolation and identification of phenolic compounds from Gynura divaricata leaves. Pharmacogn Mag. 2011 Apr;7(26):101-8.

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