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Merck
CN

S0625

D-(−)-Salicin

≥99% (GC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C13H18O7
CAS Number:
138-52-3
Molecular Weight:
286.28
Beilstein:
89593
EC Number:
205-331-6
MDL number:
MFCD00006590
UNSPSC Code:
12352205
PubChem Substance ID:
24899442
NACRES:
NA.25

Key Documents

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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

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Precautionary Statements

P280 - P302 + P352

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX9587
MKCX3386
WXBF0903V
MKCV0344
MKCR9491

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Van de Casteele S, et al.
International dairy journal, 16(12), 1470-1476 (2006)
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
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