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94419

Sigma-Aldrich

Neochlorogenic acid

from Lonicera japonica, ≥98.0% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C16H18O9
Número de CAS:
906-33-2
Peso molecular:
354.31
Número CE:
212-997-1
Número MDL:
MFCD10566639
Código UNSPSC:
12352204
ID de la sustancia en PubChem:
329770338
NACRES:
NA.32

origen biológico

Lonicera japonica

Nivel de calidad

100

Ensayo

≥98.0% (HPLC)

Formulario

powder or crystals

pérdida

≤3.0% loss on drying

aplicaciones

metabolomics
vitamins, nutraceuticals, and natural products

cadena SMILES

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

Clave InChI

CWVRJTMFETXNAD-NXLLHMKUSA-N

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Descripción general

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

Aplicación

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)

Acciones bioquímicas o fisiológicas

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.

Envase

Bottomless glass bottle. Contents are inside inserted fused cone.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
WXBF4699V
WXBF1945V
WXBD9388V
WXBD7926V
WXBD6790V

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1,5-Dicaffeoylquinic acid phyproof® Reference Substance

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PHENOLIC COMPOUNDS OF SERRATULA CENTAUROIDES AND ANXIOLYTIC EFFECT
NIKOLAEVA G
Farmacia, 67(3), 504-510 (2019)
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
Faryal Mirza et al.
The Journal of nutritional biochemistry, 52, 54-61 (2017-11-18)
Dried plum (DP), a rich source of polyphenols has been shown to have bone-preserving properties in both animal models of osteoporosis and postmenopausal women. We evaluated if DP alleviated the destruction of joints in transgenic mice (TG) that overexpress human
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
Maria Villarino et al.
Journal of agricultural and food chemistry, 59(7), 3205-3213 (2011-03-05)
Chlorogenic acid (CGA) and its isomer, neochlorogenic acid (NCGA), were found to be the major phenolic compounds in the flesh and peel of three peach cultivars. Their concentrations are especially high in immature fruits (CGA, 151-548 mg/kg; NCGA, 85-380 mg/kg)
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