Salicin

Salicin^[1]
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
CAS Number	138-52-3 ;
3D model (JSmol)	Interactive image;
Abbreviations	Glc(b)-O-Ph(2-CH2OH)
ChemSpider	388601 ;
KEGG	C01451 ;
PubChem CID	439503;
RTECS number	LZ5901700;
UNII	4649620TBZ ;
	InChI InChI=1/C13H18O7/c14/h1-4,9-18H,5-6H2;
	SMILES OCc1ccccc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O;
Properties
Chemical formula	C13H18O7
Molar mass	286.280 g·mol−1
Appearance	White crystals
Density	1.434 g/cm3
Melting point	207 °C (405 °F; 480 K)
Boiling point	240 decomp.
Solubility in water	43 g/L
Solubility in Ethanol	3 g/L
Solubility in DMSO	20 g/L
Solubility in dimethyl formamide	30 g/L
Hazards
Main hazards	Skin sensitizer / Contact dermatitis
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H317
GHS precautionary statements	P261, P272, P280, P302+352, P333+313, P362, P363, P501
NFPA 704 (fire diamond)	0 1 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

Short description: Chemical compound

Salicin is an alcoholic β-glucoside. Salicin is produced in (and named after) willow (Salix) bark. It is a biosynthetic precursor to salicylaldehyde.^[4]

Medicinal aspects

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]

References

↑ Merck Index, 11th Edition, 8293
↑ ^2.0 ^2.1 ^2.2 Haynes, William M., ed (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.312. ISBN 9781498754293.
↑ ^3.0 ^3.1 PubChem
↑ Pasteels, J. M.; Rowell-Rahier, M.; Braekman, J. C.; Dupont, A. (1983). "Salicin from host plant as precursor of salicylaldehyde in defensive secretion of Chrysomeline larvae". Physiological Entomology 8 (3): 307–314. doi:10.1111/j.1365-3032.1983.tb00362.x. https://dipot.ulb.ac.be/dspace/bitstream/2013/95098/4/ac2db4af-9a60-4c77-bdb4-6fa9e75d3003.txt.
↑ "History of Aspirin". http://inventors.about.com/library/inventors/blaspirin.htm.
↑ Daniells, S (2006-10-09). "Symrise explores cheaper alternatives in bitter-maskers". www.foodnavigator.com. http://www.foodnavigator.com/Science-Nutrition/Symrise-explores-cheaper-alternatives-in-bitter-maskers.
↑ "Willow bark | University of Maryland Medical Center". http://umm.edu/health/medical/altmed/herb/willow-bark.

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Original source: https://en.wikipedia.org/wiki/Salicin. Read more

[1] Merck Index, 11th Edition, 8293

[crc-2] 2.0 ^2.1 ^2.2 Haynes, William M., ed (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.312. ISBN 9781498754293.

[PubChemSafety-3] 3.0 ^3.1 PubChem

[4] Pasteels, J. M.; Rowell-Rahier, M.; Braekman, J. C.; Dupont, A. (1983). "Salicin from host plant as precursor of salicylaldehyde in defensive secretion of Chrysomeline larvae". Physiological Entomology 8 (3): 307–314. doi:10.1111/j.1365-3032.1983.tb00362.x. https://dipot.ulb.ac.be/dspace/bitstream/2013/95098/4/ac2db4af-9a60-4c77-bdb4-6fa9e75d3003.txt.

[5] "History of Aspirin". http://inventors.about.com/library/inventors/blaspirin.htm.

[6] Daniells, S (2006-10-09). "Symrise explores cheaper alternatives in bitter-maskers". www.foodnavigator.com. http://www.foodnavigator.com/Science-Nutrition/Symrise-explores-cheaper-alternatives-in-bitter-maskers.

[7] "Willow bark | University of Maryland Medical Center". http://umm.edu/health/medical/altmed/herb/willow-bark.

v t e Nonsteroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
Pyrazolones / Pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
Salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
Acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bumadizone Bufexamac Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
Oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam
Propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
N-Arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Flufenamic acid Flunixin Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid Flutiazin
Coxibs	Apricoxib Celecoxib Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
Other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase/Orgotein Tenidap
Items listed in bold indicate initially developed compounds of specific groups. ^#WHO-EM ^†Withdrawn drugs. ^‡Veterinary use medications.

v t e Glycosides
Bond	O-glycosidic bond N-glycosidic bond S-glycosidic bond C-glycosidic bond
Geometry	α-Glycoside β-Glycoside 1,4-Glycoside 1,6-Glycoside
Glycone	Fructoside Galactoside Glucoside Glucuronide Rhamnoside Riboside
Aglycone	Alcoholic glycoside Cardiac glycoside Bufadienolide Cardenolide Cyanogenic glycoside Glycosylamine Phenolic glycoside Anthraquinone glycoside Coumarin glycoside Flavonoid glycoside Saponin Steviol glycoside Thioglycoside