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94419

Sigma-Aldrich

Neochlorogenic acid

from Lonicera japonica, ≥98.0% (HPLC)

Synonym(s):

5-O-(trans-3,4-Dihydroxycinnamoyl)-D-quinic acid, trans-5-O-Caffeoylquinic acid

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About This Item

Empirical Formula (Hill Notation):
C16H18O9
CAS Number:
906-33-2
Molecular Weight:
354.31
EC Number:
212-997-1
MDL number:
MFCD10566639
UNSPSC Code:
12352204
PubChem Substance ID:
329770338
NACRES:
NA.32

biological source

Lonicera japonica

Assay

≥98.0% (HPLC)

form

powder or crystals

loss

≤3.0% loss on drying

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

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

InChI

1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14+,16-/m1/s1

InChI key

CWVRJTMFETXNAD-NXLLHMKUSA-N

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General description

Neochlorogenic acid is a polyphenolic compound and an ester of caffeic acid and quinic acid. It is an isomer of Chlorogenic acid.

Application

Neochlorogenic acid has been used:
  • to examine the phenolic content in the roots and aerial parts of Serratula centauroides using high performance liquid chromatography (HPLC) technique
  • to study the anti-inflammatory response of dried plum in human synovial fibroblasts (hSF) and bone resorption in rheumatoid arthritic transgenic mice
  • for the quantitative and toxicity analysis of green coffee bean extract on human liver carcinoma cell line (HepG2 cells)

Biochem/physiol Actions

Neochlorogenic acid has been found to have an inhibitory effect on the biosynthesis of melanin. Therefore it can be used on harvested fruits to prevent brown rot infection caused by Monilinia laxa. It also shows impressive antioxidant, antibacterial, antiviral and antipyretic characteristics. Neochlorogenic acid has the potential to be used in the management of acute and chronic inflammatory diseases due to its anti-inflammatory activity. It may function as chemopreventive compounds due to growth inhibition seen in breast cancer cell line MDA-MB-435.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

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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Yanjuan Wang et al.
Biomedical chromatography : BMC, 29(1), 68-74 (2014-05-21)
A simple, specific and sensitive ultra-performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) method was established and validated for simultaneous determination of neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid and geniposide in rat plasma using puerarin as an internal standard (IS). Plasma
PHENOLIC COMPOUNDS OF SERRATULA CENTAUROIDES AND ANXIOLYTIC EFFECT
NIKOLAEVA G
Farmacia, 67(3), 504-510 (2019)
Giuliana Noratto et al.
Journal of agricultural and food chemistry, 57(12), 5219-5226 (2009-06-18)
Our objective was to evaluate the cancer suppression activity of extracts from a commercial variety of yellow-fleshed peach 'Rich Lady' (RL) and a red-fleshed plum 'Black Splendor' (BS) and identify the phenolic fractions that may possess potential as chemopreventive and/or
Chao-Mei Ma et al.
Bioorganic & medicinal chemistry, 18(2), 863-869 (2009-12-17)
In our continued research on chlorogenic acid analogues and derivatives with improved bioactivity, we have synthesized some caffeoyl 5,6-anhydroquinic acid derivatives. The 1,7 acetonides of chlorogenic acid (15), and of the mono-caffeoyl 5,6-anhydroquinic acids (7-8) showed appreciable anti-HIV activity. The
Boyong Kim et al.
Journal of medicinal food, 22(3), 305-313 (2019-03-01)
Chlorogenic acid (CGA) is a major component of green coffee beans. Surfactin, a cyclic lipopeptide, is produced and secreted by Bacillus subtilis strains. In this study, bioactivities of fermented green coffee bean extract (FGCBE) and the individual compounds, CGA and
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