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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
UNSPSC Code:
12352205
NACRES:
NA.25
PubChem Substance ID:
24899442
EC Number:
205-331-6
Beilstein/REAXYS Number:
89593
MDL number:
MFCD00006590

Key Documents

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Product Name

D-(−)-Salicin, ≥99% (GC)

InChI key

NGFMICBWJRZIBI-UJPOAAIJSA-N

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

SMILES string

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

assay

≥99% (GC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Quality Level

200

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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.

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX9587
MKCX3386
WXBF0903V
MKCV0344
MKCR9491

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Genetics and bitter taste responses to goitrin, a plant toxin found in vegetables
Wooding S, et al.
Chemical Senses, 35(8), 685-692 (2010)
Drug discovery: a history (2005)
Dual anticoagulant/antiplatelet persulfated small molecules
Correia-da-Silva M, et al.
European Journal of Medicinal Chemistry, 46(6), 2347-2358 (2011)
Development and Validation of HPLC Analytical Protocol for Quantification of Salicin from Salix alba L.
Shivatare RS, et al.
Pharmaceutica Analytica Acta, 61, 2015-2015 (2015)
Biosynthesis and metabolism of beta-D-salicin: a novel molecule that exerts biological function in humans and plants
Mahdi, Jassem G
Biotechnology reports (Amsterdam, Netherlands), 4, 73-79 (2014)
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