D-(-)水杨苷,D-Salicin

D-Salicin is a natural compound that belongs to the genus of salicin. D-Salicin has a variety of biochemical properties and has been shown to have antimicrobial activity against bacteria, such as Galleria mellonella. It has also been observed to inhibit some enzyme activities, such as an acetylcholinesterase inhibitor. The optimum concentration for D-salicin is at 100 μg/mL, which is the concentration at which it presents maximum biological activity. D-Salicin binds calcium ions in a similar manner as salicin and may be used in surface methodology experiments due to its ability to bind protein surfaces.

Salicin is an alcoholic β-glucoside derived from willow bark that produces anti-inflammatory (including analgesic and antipyretic) effects very similar to that of aspirin. It acts as a non-selective COX inhibitor, exhibiting IC50 values > 100 µM for COX-1 and COX-2.2

D-(-)-Salicin analytical standard provided with w/w absolute assay, to be used for quantitative titration.

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.

Salicin, also known as salicoside or delta-salicin, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Salicin exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Within the cell, salicin is primarily located in the cytoplasm. Salicin participates in a number of enzymatic reactions. In particular, salicin can be biosynthesized from salicyl alcohol. Salicin is also a parent compound for other transformation products, including but not limited to, 2'-O-acetylsalicin, 3'-O-acetylsalicin, and 6'-O-acetylsalicin. Salicin has a bitter taste.

Salicin is an aryl beta-D-glucoside that is salicyl alcohol in which the phenolic hydrogen has been replaced by a beta-D-glucosyl residue. It has a role as a prodrug, an antipyretic, a non-narcotic analgesic, a non-steroidal anti-inflammatory drug, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor and a metabolite. It is an aryl beta-D-glucoside, an aromatic primary alcohol and a member of benzyl alcohols. It derives from a salicyl alcohol.

Title: Salicin

CAS Registry Number: 138-52-3

CAS Name: 2-(Hydroxymethyl)phenyl-b-D-glucopyranoside

Additional Names: salicoside; salicyl alcohol glucoside; saligenin-b-D-glucopyranoside

Molecular Formula: C13H18O7

Molecular Weight: 286.28

Percent Composition: C 54.54%, H 6.34%, O 39.12%

Literature References: Usually obtained by making hot water extracts from the ground bark of poplar (Populus) and willow (Salix); also found in the leaves and female flowers of the willow. Isoln from root bark of Viburnum prunifolium L., Caprifoliaceae: Evans et al., J. Am. Pharm. Assoc. 34, 207 (1945). Structure and synthesis: Irvine, Rose, J. Chem. Soc. 89, 814 (1906); Kunz, J. Am. Chem. Soc. 48, 262 (1926). Hydrolysis by acids: Moelwyn-Hughes, Trans. Faraday Soc. 25, 503 (1929). Enzymatic hydrolysis: Pigman, J. Res. Natl. Bur. Stand. 27, 6 (1941). Enzymatic hydrolysis in heavy water: Stacie, Z. Phys. Chem. 28B, 236 (1935).

Properties: Orthorhombic crystals from water, mp 199-202°. [a]D25 -62 to -67° (c = 3). [a]D20 -45.6° (c = 0.6 in abs alc), Brauns, J. Am. Chem. Soc. 47, 1292 (1925). One gram dissolves in 23 ml water, 3 ml boiling water, 90 ml alcohol, 30 ml alcohol at 60°. Soluble in alkalies, pyridine, glacial acetic acid. Practically insol in ether, chloroform. Aq solns are neutral to litmus and have a bitter taste.

Melting point: mp 199-202°

Optical Rotation: [a]D25 -62 to -67° (c = 3); [a]D20 -45.6° (c = 0.6 in abs alc), Brauns, J. Am. Chem. Soc. 47, 1292 (1925)

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

Therap-Cat: Analgesic.

Therap-Cat-Vet: Has been used as a bitter stomachic, as an antirheumatic and as an analgesic.

Keywords: Analgesic (Non-Narcotic).

COA:

Product name: D-Salicin        CAS: 138-52-3     M.F.: C₁₃H₁₈O₇     M.W._: 286.28  Batch No: 20080401   Quantity: 18 kg

References:1. Z. Phys. Chem., 1924, 109, p65