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Salicin

Salicin is a naturally occurring phenolic β-glycoside with the molecular formula C₁₃H₁₈O₇ and a molar mass of 286.28 g/mol, characterized by a salicyl alcohol moiety linked via a β-glycosidic bond to a D-glucose unit at the phenolic position.^[1] Found primarily in the bark and leaves of willow trees (genus Salix), such as Salix alba and Salix candida, as well as in aspen (Populus tremula), it appears as white crystalline needles with a melting point of 207 °C and a density of approximately 1.434 g/cm³.^[2]^[3] In nature, salicin functions as a defensive compound in plants, contributing to stress responses and exhibiting cross-immunological roles in both plants and humans.^[4] The compound's pharmacological significance stems from its metabolism in the body to salicylic acid, which inhibits cyclooxygenase enzymes and thereby exerts anti-inflammatory, analgesic, and antipyretic effects similar to aspirin.^[5] These properties have been recognized since ancient times, with records from Hippocrates around 400 BCE describing the use of willow bark infusions for pain relief and fever reduction in conditions like rheumatism.^[6] Salicin was first isolated in pure crystalline form in 1829 by French pharmacist Henri Leroux from willow bark, and its structure was elucidated in 1838 by Raffaele Piria through hydrolysis into D-glucose and salicyl alcohol.^[7] This discovery paved the way for the synthesis of acetylsalicylic acid (aspirin) in 1897 by Felix Hoffmann at Bayer, addressing the gastrointestinal side effects of salicylic acid while retaining efficacy.^[8] Today, salicin remains a key component in herbal supplements derived from willow bark, used for mild pain relief and as an alternative to synthetic NSAIDs, though clinical evidence supports its efficacy primarily through conversion to salicylic acid rather than direct action.^[9] Its role in aspirin development underscores a pivotal bridge between traditional herbal medicine and modern pharmacology, influencing ongoing research into natural salicylate derivatives for anti-inflammatory therapies.^[10]

Chemical Properties

Molecular Structure

Salicin has the molecular formula \ce{C13H18O7}.^[1] It is classified as a phenolic β-glucoside, consisting of salicyl alcohol (also known as o-hydroxybenzyl alcohol) covalently linked to β-D-glucose via a β-glycosidic bond at the anomeric carbon (C1) of the glucose unit.^[1]^[11] The core structure features a phenolic benzene ring with a hydroxymethyl group (-\ce{CH2OH}) attached ortho to the oxygen atom that forms the glycosidic linkage; this ether bond connects the ring to the glucose pyranose, which bears hydroxyl groups at carbons 2, 3, 4, and 6.^[1] The glucose moiety exhibits β-D stereochemistry, with the glycosidic oxygen in the equatorial position in the standard ^4\ce{C1} chair conformation, which enables selective recognition and hydrolysis by β-glucosidase enzymes that cleave the β-glycosidic bond to release glucose and salicyl alcohol.^[11]^[12]

Physical Characteristics

Salicin is typically obtained as a white, odorless crystalline powder in its pure form. This appearance is characteristic of the compound when isolated through natural extraction processes from plant sources.^[13]^[14] The melting point of salicin is 207 °C. It exhibits a specific optical rotation of −62° (c=3 in water), reflecting its chiral nature as a β-D-glucoside. Its density is 1.434 g/cm³. Regarding solubility, salicin dissolves in water to approximately 36–40 mg/mL at 15–25 °C and shows increased solubility in boiling water (up to 250 g/L at 60 °C); it is also soluble in ethanol (about 11 mg/mL), slightly soluble in ether and chloroform, and insoluble in benzene.^[15]^[1]^[16] Under standard storage conditions, salicin remains stable but is sensitive to light and heat, which can lead to degradation. It possesses hygroscopic properties, necessitating storage in tightly sealed containers to prevent moisture absorption.^[17]

Chemical Reactivity

Salicin undergoes hydrolysis primarily through cleavage of its β-glycosidic bond, yielding salicyl alcohol (also known as saligenin) and D-glucose. This reaction proceeds enzymatically via β-glucosidase, which catalyzes the process in biological systems, or through acid- or base-catalyzed mechanisms under chemical conditions. The balanced equation for the hydrolysis is:

\ce{C13H18O7 + H2O -> C7H8O2 + C6H12O6}

Acid hydrolysis typically requires strong acids like HCl, while enzymatic hydrolysis is specific and efficient at neutral to mildly acidic pH.^[18]^[19] The salicyl alcohol component of salicin is susceptible to oxidation, converting to salicylaldehyde or further to salicylic acid under mild oxidizing conditions. Enzymatic oxidation occurs in natural systems, such as those involving aldehyde dehydrogenases, while chemical oxidation can be achieved with agents like air exposure in alkaline media or mild oxidants. This stepwise transformation highlights the reactivity of the benzylic alcohol group.^[2]^[11] Salicin demonstrates good stability in neutral aqueous solutions at ambient temperatures but undergoes decomposition via glycosidic bond hydrolysis in strong acidic or basic environments. In acidic conditions (pH < 2), significant degradation occurs, particularly when combined with elevated temperatures, leading to reduced salicin content.^[20]^[21] Synthetic derivatives of salicin, such as acetylsalicin, are formed through esterification of the hydroxymethyl or glucose hydroxyl groups, serving as analogs to modulate solubility, stability, and bioactivity. For instance, 2-O-acetylsalicin and 6-O-acetylsalicin are prepared via selective deacetylation of peracetylated intermediates or acetyl migration under basic conditions, yielding compounds with potential pharmaceutical applications. Other ester derivatives can be synthesized similarly using acyl chlorides or anhydrides.

Natural Occurrence and Biosynthesis

Plant Sources

Salicin is primarily sourced from the bark of willow trees in the genus Salix, particularly species such as Salix alba (white willow) and Salix purpurea, where it constitutes 0.5% to 11% of the dry weight depending on the species and environmental factors.^[22]^[10] Concentrations in S. alba bark typically range from 0.5% to 2% dry weight, while higher levels up to 11% have been reported in S. purpurea.^[22]^[23] These phenolic glycosides, including salicin, serve as defense compounds in willows against herbivores and pathogens.^[24] Beyond willows, salicin occurs in other plants within the Salicaceae family, notably Populus species like Populus tremula (European aspen), where bark concentrations range from 0.5% to 10% dry weight.^[25] It is also present in birch trees (Betula spp.), such as Betula papyrifera (paper birch), though at generally lower levels than in Salicaceae.^[26] Some members of the Ericaceae family contain related salicylates, but salicin itself is less commonly reported outside of Salicaceae and Betulaceae.^[27] These plants are predominantly distributed in temperate regions of the Northern Hemisphere, including Europe, North America, and Asia, where Salix and Populus species thrive in riparian and forested habitats.^[28] Salicin concentrations in willow bark exhibit seasonal variation, often peaking in spring and autumn due to active growth phases and stress responses.^[29] Extraction of salicin traditionally involves water decoctions or ethanol infusions of willow bark, methods used historically to prepare medicinal teas or tinctures.^[30] Modern industrial processes employ solvent extraction, such as hot water at 80°C or ethanol, yielding approximately 0.5% to 2% salicin from processed bark material, with optimizations like supercritical CO₂ extraction achieving higher recovery rates up to 56% of available salicin.^[31]^[32]

Biosynthetic Pathway

The biosynthetic pathway of salicin in plants, particularly within the Salicaceae family, integrates into the broader phenylpropanoid metabolism and originates from L-phenylalanine, an amino acid derived from the shikimate pathway. The process begins with the deamination of L-phenylalanine by phenylalanine ammonia-lyase (PAL) to yield trans-cinnamic acid, followed by ortho-hydroxylation to form o-coumaric acid (2-hydroxycinnamic acid) derivatives, β-oxidation for chain shortening, and reduction to produce salicyl alcohol as a key intermediate. Salicyl alcohol is then glycosylated at the phenolic hydroxyl group using UDP-glucose, resulting in β-D-salicin. This pathway shares early steps with salicylic acid biosynthesis but diverges toward phenolic glycoside formation.^[33] Critical enzymes include PAL for the initial commitment step and a series of unidentified or partially characterized oxidoreductases and thiolases for intermediate conversions leading to salicyl alcohol. The terminal glycosylation is mediated by UDP-dependent β-glucosyltransferases (UGTs) from the UGT71 clade, such as UGT71L1 in hybrid poplar (Populus tremula × P. alba), which was validated as essential through CRISPR/Cas9 knockout experiments that abolished salicinoid accumulation. In willow (Salix purpurea), homologous enzymes UGT71L2 and UGT71L3 exhibit substrate preference for salicyl-7-benzoate, an activated intermediate, facilitating efficient glucosylation. Genome analyses in Populus have identified gene clusters, including UGT71L1 (Potri.016G014500) co-localized and co-expressed with acyltransferases like HXXXD-type BAHD enzymes, indicating coordinated transcriptional control for salicinoid diversification.^[34] Biosynthesis is tightly regulated by abiotic and biotic stresses, including mechanical wounding and herbivory, which trigger induction via phenylpropanoid pathway activation; for instance, phenolic glycoside levels, including salicin, rise 2- to 10-fold within days of defoliation in species like Populus tremuloides, serving as anti-herbivore defenses. This stress responsiveness involves signaling crosstalk with jasmonic acid and salicylic acid pathways, with higher accumulation in young leaves and under elevated CO₂ conditions.^[35] The pathway exhibits evolutionary conservation across Salicaceae, reflecting adaptation for chemical defense in poplars and willows, with UGT71 homologs present in both genera. Post-2010 omics studies, including transcriptomics and metabolomics in Populus and Salix, have uncovered co-expression networks enriched in phenylpropanoid genes and potential transporters (e.g., ABC and MATE families upregulated in response modules), illuminating the genetic architecture and intercellular trafficking of salicinoids.

Historical Development

Discovery and Isolation

The use of willow bark (Salix spp.) in traditional medicine dates back thousands of years, with records from ancient civilizations such as the Sumerians around 3500 BCE and Egyptians in the Ebers Papyrus circa 1534 BCE describing its application for pain and inflammation.^[7]^[8] In ancient Greece, Hippocrates prescribed willow bark preparations around 400 BCE to alleviate pain and reduce fever, establishing an early recognition of its therapeutic potential.^[8] The modern scientific discovery of salicin began in the early 19th century amid growing interest in natural remedies. In 1828, German pharmacologist Johann Andreas Buchner, a professor at the University of Munich, successfully isolated a bitter-tasting glycoside from willow bark extracts, which he named salicin after the Latin term Salix for willow.^[36] This marked the first purification of the compound in crystalline form, though yields were low and the material appeared as yellow needles.^[36] Subsequent refinements improved the isolation process. In 1829, French pharmacist Henri Leroux enhanced extraction techniques, yielding purer, soluble crystals of salicin in greater quantities from willow bark decoctions, facilitating further study of its properties.^[8] By 1838, Italian chemist Raffaele Piria advanced the chemical characterization by developing a hydrolysis method, treating salicin with acid to yield D-glucose and salicyl alcohol (saligenin), which was then oxidized to salicylic acid, providing insights into its structure and reactivity.^[8] These early methods laid the groundwork for understanding salicin's role as a precursor in pharmaceutical development.

Connection to Aspirin

Salicin served as the key natural precursor in the chemical pathway leading to the development of salicylic acid, the foundational compound for aspirin. In 1838, Italian chemist Raffaele Piria at the University of Pisa hydrolyzed salicin to yield salicyl alcohol (saligenin) and then oxidized it to produce salicylic acid, marking the first synthetic isolation of this active moiety from willow bark derivatives.^[37] This breakthrough enabled further exploration of salicylic acid's therapeutic potential, though initial applications were limited by its harsh gastrointestinal effects. By the mid-19th century, chemists began modifying salicylic acid to improve its tolerability. In 1853, French chemist Charles Frédéric Gerhardt first acetylated salicylic acid using acetyl chloride, yielding an impure form of acetylsalicylic acid, but he did not recognize its clinical value or pursue purification.^[37] Meanwhile, sodium salicylate—derived from salicylic acid—emerged as a more soluble and less irritating alternative, gaining clinical use for treating rheumatism in the 1870s; German physicians Salomon Stricker and Ludwig Reiss reported its efficacy in rheumatic disorders as early as 1876, building on prior trials of salicin itself.^[38] The direct link to modern aspirin crystallized in 1897 when German chemist Felix Hoffmann, working at Bayer, revisited acetylation to address salicylic acid's gastric irritation. Hoffmann synthesized a stable, pure form of acetylsalicylic acid (C₉H₈O₄) by reacting salicylic acid with acetic anhydride, resulting in a compound that retained anti-inflammatory and analgesic properties while minimizing stomach upset.^[39] This innovation stemmed from salicin's structural blueprint, as the β-glucoside's phenolic core informed the design of salicylic derivatives. Bayer patented the process in 1899 and commercialized it under the name Aspirin, rapidly establishing it as a blockbuster drug for pain, fever, and rheumatism.^[40] Key milestones underscored aspirin's evolution from salicin's legacy: during World War I, Bayer's U.S. patent expired in 1917, allowing generic production and global proliferation.^[40] By the mid-20th century, acetylsalicylic acid was recognized as the structural lead for non-steroidal anti-inflammatory drugs (NSAIDs), with salicin's phenolic scaffold inspiring subsequent analgesics like ibuprofen and naproxen that mimic its inhibitory effects on prostaglandin synthesis.^[6]

Pharmacological Aspects

Metabolism in Humans

Upon oral administration, salicin undergoes hydrolysis in the gastrointestinal tract primarily by β-glucosidases produced by intestinal bacteria, yielding salicyl alcohol (also known as saligenin). This aglycone is then absorbed across the intestinal mucosa, mainly in the distal ileum or colon, and enters the bloodstream for transport to the liver. In the liver, salicyl alcohol is oxidized to salicylic acid via a two-step enzymatic process involving alcohol dehydrogenase, which converts it to salicylaldehyde, and aldehyde dehydrogenase, which further oxidizes the aldehyde to the carboxylic acid.^[41]^[42]^[11] The pharmacokinetics of salicin-derived salicylic acid in humans reflect its prodrug nature, with peak plasma concentrations typically reached within less than 2 hours after ingestion of willow bark extracts standardized to 240 mg salicin. The elimination half-life of salicylic acid is approximately 2-3 hours at therapeutic low doses. Bioavailability of total salicylates from such extracts ranges from 50% to 70%, resulting in lower peak plasma levels compared to direct administration of equivalent synthetic salicylates; for example, a 240 mg salicin dose yields an area under the curve (AUC) equivalent to about 87 mg of acetylsalicylic acid, with average peak salicylic acid concentrations around 1.2 mg/L.^[43]^[44] Salicylic acid is the predominant metabolite, accounting for 86% of total circulating salicylates, while minor metabolites include salicyluric acid (10%, the glycine conjugate) and gentisic acid (4%). These undergo further conjugation, primarily to salicyluric acid via glycine amidation in the liver and kidneys, facilitating renal excretion; over 90% of salicylates are eliminated in urine, mostly as salicyluric acid. In contrast to aspirin, which is quickly deacetylated to salicylic acid in the gut and plasma for rapid systemic availability, salicin's multi-step hydrolysis and oxidation pathway leads to a slower onset of action and reduced peak plasma levels, contributing to its milder pharmacokinetic profile.^[43]^[43]

Therapeutic Applications

Salicin exerts primary therapeutic effects as an analgesic, anti-inflammatory, and antipyretic agent, primarily through its metabolism to salicylic acid, which inhibits cyclooxygenase (COX-1 and COX-2) enzymes to reduce prostaglandin synthesis and thereby alleviate pain, inflammation, and fever.^[45]^[46] In modern herbal medicine, salicin is commonly administered via willow bark extracts standardized to 15% salicin content, used for conditions such as osteoarthritis, headaches, and lower back pain.^[47] Typical dosages range from 120 to 240 mg of salicin per day, often divided into multiple doses for up to 6 weeks to support pain relief and joint function.^[48]^[49] Clinical evidence from meta-analyses of randomized controlled trials conducted in the 2000s demonstrates that willow bark extracts containing salicin provide pain relief comparable to low-dose aspirin, though with a slower onset of action due to gradual metabolism.^[47] These extracts have been recognized in European Union herbal monographs for their traditional use in relieving mild joint pain, feverish conditions, and symptoms of colds, flu, and headaches associated with inflammation.^[50] Beyond oral supplements, salicin finds application in cosmetics, where topical formulations leverage its antioxidant properties to mitigate signs of skin aging, such as wrinkles and loss of elasticity, by promoting collagen production and reducing oxidative stress.^[51] In veterinary medicine, salicin-containing willow bark extracts are explored for analgesic effects in animals, including pain relief in calves following procedures like disbudding, offering a natural alternative to synthetic nonsteroidal anti-inflammatory drugs.^[52] Recent research as of 2025 has explored additional pharmacological effects of salicin, including neuroprotective benefits in models of Alzheimer's-like pathology by modulating neurodegeneration pathways, alleviation of periodontitis through Tas2r143/gustducin signaling, and reduction of diabetic neuropathic pain via antioxidant mechanisms.^[53]^[54]^[55]

Safety Considerations

Salicin, the active compound in willow bark supplements, can cause side effects similar to those of salicylates, though gastrointestinal irritation is generally milder compared to synthetic aspirin due to reduced mucosal damage.^[56] Common adverse effects include stomach upset, nausea, vomiting, and tinnitus, particularly at higher doses.^[57] Allergic reactions, such as rash, itching, or severe anaphylaxis, may occur, especially in individuals sensitive to aspirin or other salicylates.^[45] Salicin is contraindicated in children under 16 years old due to the risk of Reye's syndrome associated with salicylate exposure during viral infections.^[58] It should be avoided during the third trimester of pregnancy because salicylates can cross the placenta and increase bleeding risks for both mother and fetus.^[59] Individuals with bleeding disorders, such as hemophilia, or those on anticoagulation therapy are advised against its use owing to heightened bleeding potential.^[60] Salicin may potentiate the effects of anticoagulants like warfarin, increasing the risk of bruising and hemorrhage.^[60] Concurrent use with nonsteroidal anti-inflammatory drugs (NSAIDs) can amplify gastrointestinal irritation and bleeding risks.^[49] Caution is recommended with diuretics, as salicin-derived salicylates may reduce their efficacy in lowering blood pressure and promote kidney strain.^[61] The U.S. Food and Drug Administration (FDA) does not classify salicin as generally recognized as safe (GRAS) for direct food use, though willow bark extracts appear in dietary supplements.^[62] Herbal product labels should include warnings for aspirin sensitivity, Reye's syndrome risk, and interactions with blood thinners, as recommended by the United States Pharmacopeia.^[59] Overdose symptoms mirror salicylate toxicity, including severe nausea, vomiting, tinnitus, hyperventilation, confusion, and potential metabolic acidosis; acute oral LD50 in rats is approximately 500–2000 mg/kg for related salicylates.^[63]

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Oct 17, 2023 · Information about how FDA regulates food additives that are generally recognized as safe or "GRAS."GRAS Substances (SCOGS... · GRAS Notification Program · GRAS Notice Inventory
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Salicylic acid - Registration Dossier - ECHA
All LD50 values were therefore in the range of 500 -2000 mg/kg, demonstrating that salicylic acid is harmful via the oral route. Acute dermal toxicity: Two ...Missing: salicin overdose