Salicin
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Salicin
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CAS No:
138-52-3
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Formula:
C13H18O7
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Chemical Name:
Salicin
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Synonyms:
β-D-Glucopyranoside,2-(hydroxymethyl)phenyl;Salicin;2-(Hydroxymethyl)phenyl β-D-glucopyranoside;o-(Hydroxymethyl)phenyl β-D-glucopyranoside;Salicine;Salicoside;Salicyl alcohol glucoside;Saligenin β-D-glucopyranoside;1-β-D-Glucosyloxy-2-hydroxymethylbenzene;D-Salicin;NSC 5751;30370-90-2
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CAS No:
Description
Salicin is a natural COX inhibitor.
Solid
Salicin is an aryl beta-D-glucoside that is salicyl alcohol in which the phenolic hydrogen has been replaced by a beta-D-glucosyl residue. It has a role as a prodrug, an antipyretic, a non-narcotic analgesic, a non-steroidal anti-inflammatory drug, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor and a metabolite. It is an aryl beta-D-glucoside, an aromatic primary alcohol and a member of benzyl alcohols. It derives from a salicyl alcohol.
Characteristics
119.61000
-1.2
Solid
1.504g/cm3
207 °C
549.1ºC at 760 mmHg
285.9ºC
-62 ° (C=3, H2O)
H2O: 36 g/L (15 ºC), 250 g/L (60 ºC)
Store at RT.
6.85E-13mmHg at 25°C
163.2 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Safety Information
NONH for all modes of transport
3
R43
S24/25-S37
LZ5901700
Xi
Stability Stable, but light sensitive. Incompatible with strong oxidizing agents.
P280
H317
|Warning|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501|Aggregated GHS information provided by 82 companies from 3 notifications to the ECHA C&L Inventory.
Drug Information
Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)
salicin
Salicin Use and Manufacturing
General procedure: To a solution 2 and the acceptor ArOH (3.0 equiv) in dry DCM (0.1 M) was added afreshly prepared solution of BF3•OEt2 (1.0 equiv., 1M in dry DCM). The solution wasstirred 1 h and followed by TLC (30:70; EtOAc : hexanes). A solution of NaHCO3(aq) wasadded and the mixture was extracted with DCM, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The α/β ratio was measured by 1H NMR on the crude.The residue was treated with a freshly prepared solution MeONa (0.25 equiv., 0.5 M inmethanol) in dry methanol (0.3 M). The solution was stirred at r.t. for 1 h andneutralized with Amberlite IR-120 H+, filtered and concentrated in vacuo to give a whitesolid. Quick flash column chromatography (10:90; MeOH:DCM) removed excess of ArOHand led to the β-D anomer, which was recrystallized in hot ethanol.
Standard substrate in evaluating enzyme preparations.
.beta.-D-Glucopyranoside, 2-(hydroxymethyl)phenyl: ACTIVE
Computed Properties
Molecular Weight:286.28
XLogP3:-1.2
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:4
Exact Mass:286.10525291
Monoisotopic Mass:286.10525291
Topological Polar Surface Area:120
Heavy Atom Count:20
Complexity:300
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Analgesic, antipyretic, anti-inflammatory, and anti-rheumatic effects; also has bitter stomachic and local anesthetic properties
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