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| Names | |
|---|---|
| IUPAC name 2-(Hydroxymethyl)phenyl β-D-glucopyranoside | |
| Systematic IUPAC name (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol | |
| Other names Salicin;D-(−)-Salicin; Salicoside | |
| Identifiers | |
| |
3D model (JSmol) | |
| Abbreviations | Glc(b)-O-Ph(2-CH2OH) |
| ChemSpider |
|
| ECHA InfoCard | 100.004.847 |
| KEGG |
|
| RTECS number |
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| UNII | |
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| Properties | |
| C13H18O7 | |
| Molar mass | 286.280 g·mol−1 |
| Appearance | White crystals |
| Density | 1.434 g/cm3[2] |
| Melting point | 207 °C (405 °F; 480 K)[2] |
| Boiling point | 240 decomp.[2] |
| 43 g/L | |
| Solubility inEthanol | 3 g/L |
| Solubility inDMSO | 20 g/L |
| Solubility indimethyl formamide | 30 g/L |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | Skin sensitizer /Contact dermatitis[3] |
| GHS labelling: | |
 | |
| Warning | |
| H317 | |
| P261,P272,P280,P302+P352,P333+P313,P362,P363,P501 | |
| NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Salicin is an alcoholic β-glucoside. Salicin is produced in (and named after)willow (Salix) bark. It is a biosynthetic precursor tosalicylaldehyde.[4]
Salicin hydrolyses intoβ-d-glucose andsalicyl alcohol (saligenin). Salicyl alcohol can be oxidized into salicylaldehyde and salicylate, both biologically and industrially.
Salicin is found in the bark of and leaves ofwillows, poplars and various other plants.[5] Derivates are found incastoreum. Salicin from meadowsweet was used in the synthesis ofaspirin (acetylsalicylic acid),[6] in 1899 by scientists atBayer. Salicin tastes bitter likequinine.[7]
Salicin may cause an allergic skin reaction (skin sensitization; category 1).[3]
Mild side effects are standard, with rare occurrences of nausea, vomiting, rash, dizziness and breathing problems. Overdose from high quantities of salicin can be toxic, damaging kidneys, causing stomach ulcers, diarrhea, bleeding or digestive discomfort. Some people may be allergic or sensitive to salicylates and suffer reactions similar to those produced by aspirin. People should not take salicin if they have asthma, diabetes, gout, gastritis, hemophilia, stomach ulcers; also contraindicated are children under 16, and pregnant and breastfeeding women.[8]
| pyrazolones / pyrazolidines | |
|---|---|
| salicylates | |
| acetic acid derivatives and related substances | |
| oxicams | |
| propionic acid derivatives (profens) |
|
| n-arylanthranilic acids (fenamates) | |
| COX-2 inhibitors (coxibs) | |
| other | |
| NSAID combinations | |
Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;†withdrawn drugs;‡veterinary use. | |
