CAS 2450-53-5 | Isochlorogenic acid A | CAS Number 2450-53-5

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2450-53-5 | Isochlorogenic acid A

CAS No: 2450-53-5 Catalog No: AG0039M8 MDL No:MFCD00951290

Product Description

Catalog Number:

AG0039M8

Chemical Name:

Isochlorogenic acid A

CAS Number:

2450-53-5

Molecular Formula:

C25H24O12

Molecular Weight:

516.4509

MDL Number:

MFCD00951290

IUPAC Name:

(3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylic acid

InChI:

InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23?,25?/m1/s1

InChI Key:

KRZBCHWVBQOTNZ-RDJMKVHDSA-N

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

UNII:

ND94C5E75K

Properties

Complexity:

825

Compound Is Canonicalized:

Yes

Covalently-Bonded Unit Count:

Defined Atom Stereocenter Count:

Defined Bond Stereocenter Count:

Exact Mass:

516.127g/mol

Formal Charge:

Heavy Atom Count:

Hydrogen Bond Acceptor Count:

Hydrogen Bond Donor Count:

Isotope Atom Count:

Molecular Weight:

516.455g/mol

Monoisotopic Mass:

516.127g/mol

Rotatable Bond Count:

Topological Polar Surface Area:

211A^2

Undefined Atom Stereocenter Count:

Undefined Bond Stereocenter Count:

XLogP3:

1.5

Literature

Title	Journal
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