3,4,5-Tricaffeoylquinic acid

Modify Date: 2024-01-02 21:52:36

3,4,5-Tricaffeoylquinic acid Structure
3,4,5-Tricaffeoylquinic acid structure
Common Name 3,4,5-Tricaffeoylquinic acid
CAS Number 86632-03-3 Molecular Weight 678.59
Density 1.6±0.1 g/cm3 Boiling Point 916.0±65.0 °C at 760 mmHg
Molecular Formula C34H30O15 Melting Point N/A
MSDS N/A Flash Point 290.9±27.8 °C

 Use of 3,4,5-Tricaffeoylquinic acid


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].

 Names

Name (3R,5R)-3,4,5-tris[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1-hydroxycyclohexane-1-carboxylic acid
Synonym More Synonyms

 3,4,5-Tricaffeoylquinic acid 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
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

 Synonyms

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.
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