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S0625

D-(−)-Salicin

Name: <SC>D</SC>-(−)-Salicin
Brand: SIGMA

≥99% (GC)

Sinónimos:

2-(Hydroxymethyl)phenyl-β-D-glucopyranoside, Salicoside, Salicyl alcohol glucoside, Saligenin β-D-glucoside

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Fórmula empírica (notación de Hill):

C₁₃H₁₈O₇

Número CAS:

138-52-3

Peso molecular:

286.28

UNSPSC Code:

12352205

NACRES:

NA.25

PubChem Substance ID:

24899442

EC Number:

205-331-6

Beilstein/REAXYS Number:

89593

MDL number:

MFCD00006590

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Propiedades

Quality Level

200

assay

≥99% (GC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

OC[C@H]1O[C@@H](Oc2ccccc2CO)[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C13H18O7/c14-5-7-3-1-2-4-8(7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1

InChI key

NGFMICBWJRZIBI-UJPOAAIJSA-N

Descripción

General description

Salicin is a non-phenolic glucosidic compound extracted from meadowsweet (Filipendula ulmaria L). It is majorly used as a substitute for quinine. Salicin can be used as a therapeutic for patients suffering from rheumatic fever. Salicin acts a metabolic precursor for salicylic acid. It is a novel phytochemical that exhibits immunological cross functions in plants and humans. Salicin facilitates growth and reproduction in plants. In addition, It also protects plants against biotic and abiotic stress.

Application

D-(-)-Salicin has been used:

to study its in vitro anticoagulant and antiplatelet activities
as a standard in high performance liquid chromatography method (HPLC) for quantitation of salicin from willow plant
as a tastant in taste threshold assay
as a constituent of nutrient agar-salicin medium for selective isolation of Lactobacillus paracasei

Biochem/physiol Actions

D-(−)-Salicin exerts anti-rheumatism and anti-inflammatory activities. It inhibits lipopolysaccharide (LPS) induced inflammation in in vitro and in vivo studies. It regulates different signaling pathways such as nuclear factor kappa B (NF-κB) and mitogen-activated protein kinase (MAPK). It also regulates cytokines concentration such as tumor necrosis factor-alpha(TNF-α), interleukin-1β, interleukin-6, and interleukin-10.