Salicin

Salicin[1]
IUPAC name (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3, 4,5-triol
Other names Salicin; D-(−)-Salicin; Salicoside; 2-(Hydroxymethyl)phenyl -β-D-glucopyranoside
Identifiers
CAS number	138-52-3 Y
PubChem	439503
ChemSpider	388601 N
UNII	4649620TBZ Y
KEGG	C01451 N
RTECS number	LZ5901700
Jmol-3D images	{{#if:c1ccc(c(c1)CO)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O|Image 1
SMILES c1ccc(c(c1)CO)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
InChI InChI=InChI=1/C13H18O7/c14/h1-4,9-18H,5-6H2
Properties
Molecular formula	C13H18O7
Molar mass	286.28 g mol−1
Melting point	197-200 °C
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Salicin is an alcoholic β-glucoside. Salicin is an anti-inflammatory agent that is produced from willow bark.^[2]

It is also found in castoreum, which was used as an analgesic, anti-inflammatory, and antipyretic. The activity of castoreum has been credited to the accumulation of salicin from willow trees in the beaver's diet, which is transformed to salicylic acid and has an action very similar to aspirin.^[3]

Salicin is closely related in chemical make-up to aspirin. When consumed, the acetalic etherbridge is broken down. The two parts of the molecule, glucose and salicylic alcohol, then are metabolized separately. By oxidizing the alcohol function the aromatic part finally is metabolized to salicylic acid.

Salicin elicits bitterness like quinine, when consumed.^[4]

Alkaline cleavage of the glucoside populin produces benzoate and salicin.^[5]

Salicin may be used by some people that are limited to, or prefer, natural medicinal sources, as an anti-inflammatory, headache or pain relief, easing symptoms of arthritis, acne, psoriasis and warts. For reasons of safety, lower risk of side effects, and negative interaction with prescriptions such as gastrointestinal pain from ibuprofen and other non-steroidal anti-inflammatory drugs (NSAIDs).

Salicin in small amounts is found in some foods, including berries, olives, mushrooms, nuts, almonds, seeds, raisins, tomatoes, radish, chicory, green pepper, alfalfa, broccoli, spinach, sweet potato, along with some spices such as curcuma, curry, turmeric, cumin, thyme, oregano, rosemary and mustard. Higher amounts are found in some herbs such as meadowsweet, wintergreen, especially wintergreen oil, poplar tree, sweet and white birch.

Salicylates aid in blood thinning, lowering production of two enzymes, prostaglandins and thromboxanes, which reduces inflammation and the potential of platelets to stick to one another, by acting as a natural oil cleanser to wipe up the sticky and greasy layer on platelet surfaces, lessening risk of blood clots, heart attacks and strokes. In addition, salicylates reduce additional tissue damage after coronary artery disease or heart attacks, as the blood thinner properties allow for better bloodflow through clogged arteries, while possibly reducing risk of cancer as angiogenesis of cancerous cells is associated with chronic inflammation.

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, stomach causing ulcers, diarrhea, bleeding or digestive discomfort. Some people may be allergic, or sensitive to salicylates, similar to reactions to aspirin. Others that are advised against taking salicin are those with asthma, diabetes, gout, gastritis, hemophilia, stomach ulcers, children under 16, pregnant and breastfeeding women. ^[6][7]

References