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3,4,5-Tricaffeoylquinic acid

Names

[ CAS No. ]:
86632-03-3

[ Name ]:
3,4,5-Tricaffeoylquinic acid

[Synonym ]:
Cyclohexanecarboxylic acid, 3,4,5-tris(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1-hydroxy-, (1α,3R,4α,5R)-
(3R,5R)-3,4,5-Tris{[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]oxy}-1-hydroxycyclohexanecarboxylic acid
3,4,5-tricaffeoylquinic acid
3,4,5-tri-CQA
Cyclohexanecarboxylic acid, 3,4,5-tris[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1-hydroxy-, (3R,5R)-
Caffeoylquinic acid der.

Biological Activity

[Description]:

3,4,5-Tricaffeoylquinic acid is isolated from barks of Ilex rotunda Thunb, used in the research of the pro-inflammatory mediator-induced skin disease[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Inflammation/Immunology

[In Vitro]

3,4,5-Tricaffeoylquinic acid (0-50 μM) reduces TNF-α-induced production of cytokines in HEK001 keratinocytes[1]. 3,4,5-Tricaffeoylquinic acid (15 μM, 35 min) inhibits TNF-α-induced IkBα phosphorylation and activation of NF-κB[1]. Cell Viability Assay[1] Cell Line: Keratinocytes Concentration: 15, 25 and 50 μM Incubation Time: 24 hours Result: Cell death was cell ∼4-5% at 15 and 25 μM, ∼9% at 50 μM. Western Blot Analysis[1] Cell Line: Keratinocytes Concentration: 15 μM Incubation Time: 20 min before 10 ng/mL TNF-α addition for 15 min Result: Decreased TNF-α-induced-IkBα phosphorylation of IkBα and levels of cytosolic NF-Κb p65, cytosolic NF-Κb p65.

[References]

[1]. Lee CS, et al. 3,4,5-Tricaffeoylquinic acid inhibits tumor necrosis factor-α-stimulated production of inflammatory mediators in keratinocytes via suppression of Akt- and NF-κB-pathways. Int Immunopharmacol. 2011 Nov;11(11):1715-23.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
916.0±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C34H30O15

[ Molecular Weight ]:
678.59

[ Flash Point ]:
290.9±27.8 °C

[ Exact Mass ]:
678.158447

[ PSA ]:
257.81000

[ LogP ]:
2.68

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.737

[ Storage condition ]:
2-8°C

Related Compounds