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HomeProduct name listD-(-)-Salicin

D-(-)-Salicin

Synonym(s):D-(−)-Salicin;2-(Hydroxymethyl)phenyl-β-D-glucopyranoside;Salicoside;Salicyl alcohol glucoside;Saligenin β-D-glucoside

  • CAS NO.:138-52-3
  • Empirical Formula: C13H18O7
  • Molecular Weight: 286.28
  • MDL number: MFCD00006590
  • EINECS: 205-331-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:08:52
D-(-)-Salicin Structural

What is D-(-)-Salicin?

Chemical properties

white crystals or powder

The Uses of D-(-)-Salicin

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

The Uses of D-(-)-Salicin

analgesic, antipyretic

The Uses of D-(-)-Salicin

H1 antihistamine (nonsedating)

The Uses of D-(-)-Salicin

Standard substrate in evaluating enzyme Preparations contg b-glucosidase: Weidenhagen, Z. Ver. Zucker-Ind. 79, 591 (1929).

What are the applications of Application

D-(?)-Salicin is an inhibitor of Cox

Definition

ChEBI: An aryl beta-D-glucoside that is the beta-D-glucoside of the phenolic hydroxy group of salicyl alcohol.

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.

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.

Purification Methods

Crystallise D(-)-salicin from EtOAc, EtOH or water and sublime it at 190-195o/12mm. [Armour et al. J Chem Soc 412 1961, IR: Pearl & Darling J Org Chem 24 731 1959, Beilstein 17 III/IV 2986, 17/7 V 113.]

Properties of D-(-)-Salicin

Melting point: 196-202 °C
Boiling point: 388.65°C (rough estimate)
alpha  -61.5 º (c=5, water)
Density  1.4340
refractive index  -62 ° (C=3, H2O)
storage temp.  2-8°C
solubility  36g/l
form  Fine Crystalline Powder
pka 12.80±0.70(Predicted)
color  White
Water Solubility  36 g/L (15 ºC), 250 g/L (60 ºC)
Merck  14,8324
BRN  89593
Stability: Stable, but light sensitive. Incompatible with strong oxidizing agents.
CAS DataBase Reference 138-52-3(CAS DataBase Reference)
NIST Chemistry Reference Salicin(138-52-3)
EPA Substance Registry System .beta.-D-Glucopyranoside, 2-(hydroxymethyl)phenyl (138-52-3)

Safety information for D-(-)-Salicin

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H317:Sensitisation, Skin
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.

Computed Descriptors for D-(-)-Salicin

InChIKey NGFMICBWJRZIBI-MICYEWLZSA-N

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