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Cynarin

analytical standard

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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
Empirical Formula (Hill Notation):
C25H24O12
CAS Number:
30964-13-7
Molecular Weight:
516.45
MDL number:
MFCD11112054
UNSPSC Code:
85151701
PubChem Substance ID:
329770082
NACRES:
NA.24

grade

analytical standard

Quality Level

100

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
Lourdes Santana et al.
Journal of medicinal chemistry, 51(21), 6740-6751 (2008-10-07)
The work provides a new model for the prediction of the MAO-A and -B inhibitor activity by the use of combined complex networks and QSAR methodologies. On the basis of the obtained model, we prepared and assayed 33 coumarin derivatives
Denis Fourches et al.
Chemical research in toxicology, 23(1), 171-183 (2009-12-18)
Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental drug discovery projects toward safer medicines. In this

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