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| Targets |
Salicin itself is not a direct inhibitor of cyclooxygenase (COX); rather, it is converted in the body to salicylic acid, which irreversibly inhibits COX-1 and COX-2 enzymes, reducing the synthesis of prostaglandins and thromboxanes. This results in decreased inflammation, pain, and fever. Salicin may also have additional effects via modulation of NF-κB and MAPK pathways, contributing to its anti-inflammatory actions.
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| ln Vitro |
In comparison to the COLO control, there was a notable downregulation of PGE2 (the enzymatic product of COX2) in the lysate and supernatant after treating COLO cells with salicin at a concentration of 10 μM. ..This was concomitant with a minimal genetic COX1 inhibition of 91% of CCD controls. Colon cancer cell growth was lowered by 1 μM salicin treatment, from 144% to 113% at 24 hours and from 187% to 130% at 48 hours. The proliferation rate was lowered to 108% after 24 hours and 108% after 48 hours of treatment with 10 μM. In 48 hours, it fell to 119%[1]. The LPS-induced cells pretreated with 0.07, 0.14, and 0.28 μM salicin had considerably lower amounts of TNF-α, IL-1β, and IL-6 than the LPS group [2].
In vitro, salicin exhibits moderate antioxidant activity, scavenging free radicals and reducing lipid peroxidation. It has been shown to inhibit COX-2 expression in LPS-stimulated macrophages, although its direct COX inhibition is weak. Salicin also demonstrates neuroprotective effects in neuronal cell cultures by reducing oxidative stress and apoptosis. Its antimicrobial activity is limited, but it may have some effects against certain bacteria and fungi. |
| ln Vivo |
LPS-induced p athological alterations were considerably reduced by salicin (D(-)-Salicin) (35, 70, 140 mM). When compared to the control group, there was a substantial increase in LPS-induced MPO activity in lung tissue. But salicin (35, 70, and 140 μM) strongly prevented this alteration. In a dose-dependent way, salicin pretreatment can block the activation of JNK, ERK, p38/MAPK, and p65 produced by LPS [2].
In vivo, salicin is effective as an analgesic and anti-inflammatory agent in animal models. In rats, oral administration of salicin reduces carrageenan-induced paw edema and acetic acid-induced writhing responses. It also lowers fever in febrile animal models. In humans, salicin from willow bark extract has been shown to reduce pain in osteoarthritis and lower back pain, with efficacy comparable to low-dose aspirin. Its onset of action is slower than aspirin due to the need for metabolic conversion. |
| Enzyme Assay |
In vitro enzyme/receptor binding assays for salicin are not direct because it is a prodrug. However, its metabolite salicylic acid can be tested for COX-1 and COX-2 inhibition using purified enzymes. The IC50 for COX-1 and COX-2 is determined by measuring prostaglandin production. Salicin itself does not bind significantly to COX enzymes. Its antioxidant activity is assessed by DPPH and ABTS radical scavenging assays.
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| Cell Assay |
In vitro cellular assays for salicin are performed using macrophages or neuronal cells. Cells are treated with salicin, and its effects on COX-2 expression, NO production, and cytokine release are measured after LPS stimulation. Western blotting and ELISA are used. Neuroprotective effects are studied in cells exposed to oxidative stress, measuring cell viability and ROS levels. Cell viability is assessed by MTT assays.
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| Animal Protocol |
In vivo animal experiments for salicin are conducted in rats and mice. Analgesic activity is evaluated using the tail-flick test and acetic acid-induced writhing. Anti-inflammatory effects are measured in carrageenan-induced paw edema. Antipyretic activity is assessed in yeast-induced fever models. Salicin is administered orally or intraperitoneally, and doses range from 50 to 500 mg/kg. Blood samples are collected to measure salicylic acid levels.
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| ADME/Pharmacokinetics |
Salicin has a molecular weight of 286.28 g/mol and a molecular formula of C13H18O7. It is a white crystalline powder, soluble in hot water, ethanol, and methanol. Oral bioavailability of salicin is about 30-40% in humans. It is absorbed from the intestine and metabolized by intestinal bacteria and liver enzymes to salicylic acid. The half-life of salicin is short (about 1-2 hours), but its metabolite salicylic acid has a longer half-life. Excretion is via urine as conjugates.
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| Toxicity/Toxicokinetics |
Salicin is generally considered safe and well-tolerated. Common adverse effects include mild gastrointestinal upset, nausea, and dizziness, similar to aspirin but less frequent. At high doses, it may cause gastrointestinal bleeding and allergic reactions in sensitive individuals. Salicin should be avoided in patients with aspirin allergy, peptic ulcers, or bleeding disorders. The therapeutic index is relatively wide, and toxicity is rare at recommended doses.
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| References | |
| Additional Infomation |
Salicin is an aryl β-D-glucoside, a compound in which the phenolic hydroxyl hydrogen in salicylol is replaced by a β-D-glucose residue. It possesses various pharmacological effects, including function as a prodrug, antipyretic, non-narcotic analgesic, nonsteroidal anti-inflammatory drug, EC 1.14.99.1 (prostaglandin intraperoxidase synthase) inhibitor, and a metabolite. It is an aryl β-D-glucoside, belonging to the aromatic primary alcohol class and the benzyl alcohol group. Its function is related to that of salicylol. Salicin is a metabolite found or produced in Escherichia coli (K12 strain, MG1655 strain). It has also been reported that salicin is present in gardenia, Itodon orientalis, and other organisms with relevant data.
Salicin is a natural glycoside found in willow bark, used traditionally as a remedy for pain and fever. It is the precursor to aspirin (acetylsalicylic acid). Salicin is available as a dietary supplement and is sometimes used in herbal medicine for osteoarthritis and low back pain. Its anti-inflammatory and analgesic effects are mediated through its conversion to salicylic acid. Unlike aspirin, salicin does not irreversibly inhibit platelets, making it a milder alternative. It is not an FDA-approved drug but is recognized as a safe ingredient in supplements. |
| Molecular Formula |
C13H18O7
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|---|---|
| Molecular Weight |
286.28
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| Exact Mass |
286.105
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| CAS # |
138-52-3
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| PubChem CID |
439503
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
549.1±50.0 °C at 760 mmHg
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| Melting Point |
196-202 °C
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| Flash Point |
285.9±30.1 °C
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| Vapour Pressure |
0.0±1.6 mmHg at 25°C
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| Index of Refraction |
1.638
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| LogP |
-1.85
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
20
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| Complexity |
300
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C1=CC=C(C(=C1)CO)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
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| InChi Key |
NGFMICBWJRZIBI-UJPOAAIJSA-N
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| InChi Code |
InChI=1S/C13H18O7/c14-5-7-3-1-2-4-8(7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1
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| Chemical Name |
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
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| Synonyms |
NSC-5751; NSC 5751; Salicin
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~150 mg/mL (~523.96 mM)
H2O : ~12.5 mg/mL (~43.66 mM) |
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4931 mL | 17.4654 mL | 34.9308 mL | |
| 5 mM | 0.6986 mL | 3.4931 mL | 6.9862 mL | |
| 10 mM | 0.3493 mL | 1.7465 mL | 3.4931 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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