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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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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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Drug discovery: a history (2005)
Genetics and bitter taste responses to goitrin, a plant toxin found in vegetables
Wooding S, et al.
Chemical Senses, 35(8), 685-692 (2010)
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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