Loading AI tools
Chemical compound From Wikipedia, the free encyclopedia
Salicin is an alcoholic β-glucoside. Salicin is produced in (and named after) willow (Salix) bark. It is a biosynthetic precursor to salicylaldehyde.[4]
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 | |
PubChem CID |
|
RTECS number |
|
UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
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 in Ethanol | 3 g/L |
Solubility in DMSO | 20 g/L |
Solubility in dimethyl 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 their standard state (at 25 °C [77 °F], 100 kPa).
|
Salicin hydrolyses into β-d-glucose and salicyl alcohol (saligenin). Salicyl alcohol can be oxidized into salicylaldehyde and salicylate, both biologically and industrially.
Salicin is found in the bark of and leaves of willows, poplars and various other plants. Derivates are found in castoreum. Salicin from meadowsweet was used in the synthesis of aspirin (acetylsalicylic acid),[5] in 1899 by scientists at Bayer. Salicin tastes bitter like quinine.[6]
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.[7]
Seamless Wikipedia browsing. On steroids.
Every time you click a link to Wikipedia, Wiktionary or Wikiquote in your browser's search results, it will show the modern Wikiwand interface.
Wikiwand extension is a five stars, simple, with minimum permission required to keep your browsing private, safe and transparent.