D-(-)-Salicin Chemical Properties

Melting point:

196-202 °C

alpha 

-61.5 º (c=5, water)

Boiling point:

388.65°C (rough estimate)

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.

InChIKey

NGFMICBWJRZIBI-MICYEWLZSA-N

LogP

-1.232 (est)

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

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

36/37-37-24/25-36

WGK Germany 

3

RTECS 

LZ5901700

F 

3-10

TSCA 

Yes

HS Code 

29389090

MSDS

• Language:English Provider:2-(Hydroxymethyl)phenyl-beta-D-glucopyranoside
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

D-(-)-Salicin Usage And Synthesis

Description

D(-)-Salicin is a traditional medicine which has been known to exhibit anti-inflammation and other therapeutic activities, it can inhibit the LPS-induced inflammation in RAW264.7 cells and mouse models.

Chemical Properties

white crystals or powder

Uses

analgesic, antipyretic

Uses

H1 antihistamine (nonsedating)

Uses

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

Uses

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

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.]

D-(-)-Salicin(138-52-3)Related Product Information

• Icariin
• Ursolic acid
• Matrine
• Willow Bark Extract
• Salicylamide
• WhiteWillowBarkExtract
• Salicin benzoate,2-(hydroxymethyl)phenyl-beta-D-glucopyranoside 6-benzoate
• D-(-)-Salicin
• CURCULIGOSIDE
• SAPONARIN
• Salicylaldehyde
• TETRAHYDRO-2-(2-PROPYNYLOXY)-2H-PYRAN
• PHENYL-BETA-D-GLUCOPYRANOSIDE
• (2'-METHOXYCARBONYL)PHENYL-2-,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE
• (2'-METHOXYCARBONYL) PHENYL-BETA-D-GLUCOPYRANOSIDE
• LEIOCARPOSIDE
• ALOENIN A
• MYCOPHENOLIC ACID GLUCURONIDE