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Merck

S0625

D-(−)-Salicin

≥99% (GC)

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C13H18O7
Numéro CAS:
Poids moléculaire :
286.28
UNSPSC Code:
12352205
NACRES:
NA.25
PubChem Substance ID:
EC Number:
205-331-6
Beilstein/REAXYS Number:
89593
MDL number:
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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

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.


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Hazard Classifications

Skin Sens. 1

Classe de stockage

11 - Combustible Solids

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Autofluorescence-based identification and functional validation of antennal gustatory sensilla in a specialist leaf beetle
Pentzold S, et al.
Frontiers in Physiology, 10, 343-343 (2019)
Maik Behrens et al.
Chemical senses, 38(6), 475-484 (2013-05-02)
Mutational polymorphism in the TAS2R38 bitter taste receptor is a key determinant of threshold taste detection of isolated compounds, such as phenylthiocarbamide (PTC) and propylthiouracil (PROP), as well as complex orosensation-mediated traits such as diet choice and smoking habits. These
Evaluation of culture media for selective enumeration of probiotic strains of lactobacilli and bifidobacteria in combination with yoghurt or cheese starters
Van de Casteele S, et al.
International dairy journal, 16(12), 1470-1476 (2006)