Salicin from plant extract

• CAS: 138-52-3
• Catalog Number: ACM138523
• Category: Main Products
• Molecular Weight: 286.28
• Molecular Formula: C₁₃H₁₈O₇
• Synonyms: Salix alba L.; 2-(Hydroxymethyl)phenyl-β-D-glucopyranoside; Salicine; SALICIN; 2-(Hydroxymethyl)phenyl β-D-glucopyranoside; WHITE WILLOW; Salicin; D-(−)-Salicin; D(-)-Salicin; (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(2-(hydroxymethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triol; SALICOSIDE; 2-(Hydroxymethyl)phenyl-beta-D-glucopyranoside
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
• Canonical SMILES: C1=CC=C(C(=C1)CO)OC2C(C(C(C(O2)CO)O)O)O
• InChI Key: NGFMICBWJRZIBI-UJPOAAIJSA-N
• Boiling Point: 549.1ºC at 760 mmHg
• Melting Point: 197-200ºC
• Flash Point: 285.9ºC
• Density: 1.504g/cm³
• Appearance: White to gray powder
• EC Number: 205-331-6
• Exact Mass: 286.10500
• Hazard Statements: Xi:Irritant
• Safety Description: S24/25-S37
• Stability: Stability Stable, but light sensitive. Incompatible with strong oxidizing agents.
• WGK Germany: 3

Case Study

Antimicrobial Activity of Salicin from the Stem Bark of Salix Tetrasperma ROXB

Ramadhani S, Santoni A, et al. IJFAC (Indonesian Journal of Fundamental and Applied Chemistry), 2019, 4(2), 47-52.

This work investigated the extraction, separation, structural identification and antimicrobial activity of salicin from the bark of Salix tetragonum. The extraction method used n-hexane, ethyl acetate and methanol solvent immersion method. The resistance of the stem bark to Escherichia coli and Staphylococcus aureus was evaluated using the disk diffusion method.
Antibacterial activity evaluation of salicin
· Sterile paper discs with a diameter of 6 mm were treated with n-hexane, ethyl acetate, methanol solvents, and salicin compound (20 μL each). The extracts were prepared at concentrations of 1000, 500, and 250 μg/mL. These paper discs were then placed on Mueller-Hinton agar (MHA) media and incubated at room temperature for 24 hours. Amoxicillin at 250 μg/mL served as the positive control, while DMSO at 100% and methanol acted as the negative control. The presence of a clear zone around the discs indicated bacterial sensitivity. The diameters of these clear zones were measured both horizontally and vertically with a ruler.
· Among the extracts tested, the ethyl acetate extract exhibited the largest clear zone diameter against Staphylococcus aureus, measuring 14.5 ± 0.5 mm. This was followed by the methanol extract at 12.7 ± 0.6 mm and salicin at 10.2 ± 0.3 mm. For Escherichia coli, the n-hexane extract yielded the largest clear zone diameter, measuring 11.7 ± 0.8 mm.

HPLC Quantitative Analysis Method for Salicin

Shivatare R S, et al. Invent Rapid: Pharm Anal Qual Assur, 2014, 1, 1-6.

White willow is the original source of salicin, a weak precursor of aspirin. A new rapid, simple and accurate gradient quantitative HPLC method was developed and validated for the determination of salicin in white willow. Specifically, a reversed phase HPLC system, paired with a diode array UV spectrometer, was established for the quantitative and qualitative standardization of salicin. Salicin was separated using a Phenomenex C18 column, and the mobile phase consisted of 0.1% orthophosphoric acid in water and acetonitrile, utilizing a gradient elution process.
Sample preparation and HPLC analysis method
· Preparation of the standard solution mixture: Approximately 6 mg of salicin was dissolved in a 25 mL volumetric flask and thoroughly mixed. This resulted in the standard stock solution. Subsequently, 3.5 mL of the standard stock solution was diluted to a final volume of 5 mL with methanol. The solution was then filtered through a 0.45-μm syringe filter, and the filtered solution served as the standard working solution.
· Preparation of the test solution: 200 mg of Salix alba extract was accurately weighed and placed in a 20 mL volumetric flask. About 15 mL of diluent was added, and the mixture was sonicated in an ultrasonic water bath for 30 minutes. After cooling, the volume was adjusted to the mark with diluent. The resulting solution was filtered first through filter paper and then through a 0.45 μm syringe filter, and this filtered solution was utilized as the test solution.

Synthetic Use

Upstream Synthesis Route 1

• 16643-37-1

• 138-52-3

Reference: [1] Synthesis (Germany), 2016, vol. 48, # 20, p. 3575 - 3588

Upstream Synthesis Route 2

• 29836-40-6

• 138-52-3

Reference: [1] Journal of Natural Products, 2004, vol. 67, # 4, p. 659 - 663

Upstream Synthesis Route 3

• 2280-44-6
• 90-01-7

• 7724-09-6
• 138-52-3

Reference: [1] Tetrahedron Asymmetry, 2010, vol. 21, # 16, p. 2060 - 2065

Upstream Synthesis Route 4

• 14581-83-0

• 138-52-3

Reference: [1]Cesko-Slovenska Farmacie,1956,vol. 5,p. 399
Chem.Abstr.,1957,p. 8690

Downstream Synthesis Route 1

• 138-52-3

• 7234-31-3

Reference: [1]Journal of the American Chemical Society,1934,vol. 56,p. 2495

* For details of the synthesis route, please refer to the original source to ensure accuracy.