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91801

Supelco

Cynarin

analytical standard

Synonym(s):

1,3-Dicaffeoylquinic acid, (1R,3R,4S,5R)-1,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-4,5-dihydroxycyclohexanecarboxylic acid, 1,5-DQA, 1,5-Dicaffeoylquinic acid, Cynarin, Cynarine

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About This Item

Empirical Formula (Hill Notation):
C25H24O12
CAS Number:
Molecular Weight:
516.45
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.24

grade

analytical standard

Quality Level

assay

≥98.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

impurities

≤10.0% water

application(s)

food and beverages

format

neat

storage temp.

2-8°C

SMILES string

O[C@@H]1C[C@](C[C@@H](OC(=O)\C=C\c2ccc(O)c(O)c2)[C@H]1O)(OC(=O)\C=C\c3ccc(O)c(O)c3)C(O)=O

InChI

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

InChI key

YDDUMTOHNYZQPO-RVXRWRFUSA-N

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General description

Cynarin is an active constituent of artichoke plant, exhibiting choleretic and hypocholesterolemic activities. It is also widely used in phytoterapic preparations with special indication in hepatic affections.

Application

Cynarin may be used as an analytical reference standard for the quantification of the analyte in plasma samples using high-performance liquid chromatography technique.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Phenolic compound found in artichoke. Antioxidant and choleretic properties. Potential immunosuppressive agent.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

This compound is commonly found in plants of the genus: arnica echinacea

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Validated HPLC method for cynarin determination in biological samples
Alonso RM, et al.
Acta Acad. Med. Sin., 25(2), 267-267 (2006)
Guo-Chung Dong et al.
Journal of medicinal chemistry, 49(6), 1845-1854 (2006-03-17)
AFTIR (after flowing through immobilized receptor) is a novel method for screening herbal extracts for pharmaceutical properties. Using AFTIR, we identified Cynarin in Echinacea purpurea by its selective binding to chip immobilized CD28, a receptor of T-cells, which is instrumental
Esra Erikel et al.
Journal of ethnopharmacology, 237, 171-181 (2019-03-21)
Cynarin is an artichoke phytochemical that possesses a variety of pharmacological features including free-radical scavenging and antioxidant activity. The origin of artichoke species appears to be Mediterranean region. Two of these species, globe artichoke (Cynara cardunculus var. scolymus L.) and
Yi Wang et al.
Bioorganic & medicinal chemistry letters, 21(23), 7064-7067 (2011-10-22)
The complex and highly impermeable cell wall of Mycobacterium tuberculosis (Mtb) is largely responsible for the ability of the mycobacterium to resist the action of chemical therapeutics. An L-rhamnosyl residue, which occupies an important anchoring position in the Mtb cell
Bianca Sperl et al.
Bioorganic & medicinal chemistry letters, 19(12), 3305-3309 (2009-05-12)
In this Letter, we report the natural products salvianolic acid A, salvianolic acid B, and caftaric acid as inhibitors of the protein-protein interactions mediated by the SH2 domains of the Src-family kinases Src and Lck, two established disease targets. Moreover

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