Methyl salicylate: Difference between revisions
Jump to navigation
Jump to search
(Created page with "{{Compound|aka=oil of wintergreen|chemf=C8H8O3 |mm=152|density=1.174|mp=-9|bp=220|sol_aq=0.639|sol_et=soluble |nfpa_h=2|nfpa_f=1}} ==Uses== * Pleasant minty smell & taste. * Trivially broken down into two useful chemicals: methanol and phenol: * Feedstock for salicylic acid, a precursor to asprin and pepto bismol ==Natural occurrence== * Many plants produce this material biologically, including betula lenta...") |
(→Uses) |
||
| Line 5: | Line 5: | ||
* Pleasant minty smell & taste. | * Pleasant minty smell & taste. | ||
* Trivially broken down into two useful chemicals: [[methanol]] and [[phenol]]: | * Trivially broken down into two useful chemicals: [[methanol]] and [[phenol]]: | ||
==Natural occurrence== | ==Natural occurrence== | ||
* Many plants produce this material biologically, including [[betula lenta]], [[gaultheria procumbens]], [[salix alba]], and [[filipendula ulmaria]] | * Many plants produce this material biologically, including [[betula lenta]], [[gaultheria procumbens]], [[salix alba]], and [[filipendula ulmaria]] | ||
Latest revision as of 21:12, 2 December 2024
| Chemical formula | C8H8O3 |
|---|---|
| Molar Mass(g/mol) | 152 |
| Density(g/cc) | 1.174 |
| Melting Point(°C) | -9 |
| Boiling Point(°C) | 220 |
| Solubility in water(g/L) | 0.639 |
| Solubility in ethanol(g/L) | soluble |
| NFPA 704 |  1
2
0
|
Uses
Natural occurrence
- Many plants produce this material biologically, including betula lenta, gaultheria procumbens, salix alba, and filipendula ulmaria
Hazards
- 7-10g taken orally is fatal for adults. 4g for children.
Production
Extraction
Steam distillation
- Methyl salicylate is produced by maceration and steam distillation of the leaves of wintergreens such as Gaultheria procumbens[1] or the bark of betula lenta, with the heavier oil removed via a dean-stark trap, and the water returned to the still.
Solvent extraction
- Methyl salicylate may be leached from the leaves of Teaberry or the twigs of sweet birch by ethanol.
Synthesis
- Fischer Esterifying methanol with salicylic acid over sulfuric acid gives methyl salicylate
- CH3OH + C7H6O3{H2SO4C8H8O3 + H2O}→
- CH3OH + C7H6O3
Purification
- Wintergreen oil is soluble in diethyl ether but not in water. A liq/liq extraction would remove water soluble impurities.
See Also
Documents
- Kennedy, George W. (1882) "Oleum Betulae Lentae"
American Journal of Pharmacy 56
link courtesy Henrietta's Herbal.
Publications
- Power, By Prof Dr Frederick B (1890) "ON THE COMPOSITION OF THE OILS WINTERGREEN AND BIRCH AND THE CHARACTERS OF THE SYNTHETIC OIL OF WINTERGREEN"
The Chemical News and Journal of Physical Science 62 Edwin John Davy, London.
link courtesy Google Books.
References
- ↑ (1911) "Harvesting and Collecting Wintergreen"
American Druggist and Pharmaceutical Record 58(Mar); pp44.