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1,5-Dicaffeoylquinic acid

analytical standard

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Synonym(s):
(1S,3R,4R,5R)-1,3-Bis[3-(3,4-dihydroxyphenyl)acryloyloxy]-4,5-dihydroxycyclohexanecarboxylic acid, 1,3-Dicaffeoylquinic acid
Empirical Formula (Hill Notation):
C25H24O12
CAS Number:
19870-46-3
Molecular Weight:
516.45
MDL number:
MFCD13196505
UNSPSC Code:
85151701
PubChem Substance ID:
329751413
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-PSEXTPKNSA-N

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General description

Dicaffeoylquinic acid is naturally occurring polyphenolic compound found in plants like fennel and coffee. It is characterized by two caffeic acid molecules linked via ester bonds to one quinic acid molecule. 1, 5-Dicaffeoylquinic acid (1,5-DCQA) is considered as a potent and nontoxic inhibitor of HIV-1 replication.
Dicaffeoylquinic acid is naturally occurring polyphenolic compound found in plants like fennel and coffee. It is characterized by two caffeic acid molecules linked via ester bonds to one quinic acid molecule. 1, 5-Dicaffeoylquinic acid (1,5-DCQA) is considered as a potent and nontoxic inhibitor of HIV-1 replication.
In literature, CAS Numbers 19870-46-3 and 30964-13-7 are each described as 1,3-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, and cynarin. The IUPAC synonym for this product is provided for clarification.

Application

It may be used as reference standard in LC-MS/MS method for the determination of 1,5-DCQA from human plasma.
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

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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Ruolan Gu et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 852(1-2), 85-91 (2007-02-03)
1,5-Dicaffeoylquinic acid (1,5-DCQA), a potent HIV-1 integrase inhibitor, is undergoing an evaluation as a promising novel HIV therapeutic agent. Here, we report a simple, rapid and robust LC-MS/MS method for simultaneous determination of 1,5-DCQA and its two active metabolites, 1-caffeoyl-5-feruoylquinic
Reham Wagdy et al.
Journal of food science, 84(5), 1012-1022 (2019-04-25)
Dietary phenolics are known for their potent antioxidant and anti-inflammatory activities, making them promising candidates for protection against neuroinflammation and neurodegeneration. Hydroalcohol extract of Egyptian species of Corchorus olitorius L. (Co) leaves was investigated for its neuroprotective effects in a
Muhammad Mir Showkat et al.
Molecules (Basel, Switzerland), 24(18) (2019-09-13)
Phenolic acids including chlorogenic acids are major polyphenolic compounds found in Jerusalem artichoke (Helianthus tuberosus L.). The plant itself is an emerging biorefinery crop due to the inulin-rich tubers, a bioethanol feedstock, but the aerial parts represent a rich source
Daniil N Olennikov et al.
Antioxidants (Basel, Switzerland), 8(8) (2019-08-17)
Fringed sagewort (Artemisia frigida Willd., Compositae family) is a well-known medicinal plant in Asian medical systems. Fifty-nine hydroxycinnamates and flavonoids have been found in A. frigida herbs of Siberian origin by high-performance liquid chromatography with diode array and electrospray triple

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