| Identification | More | [Name]
2-(Hydroxymethyl)phenyl-beta-D-glucopyranoside | [CAS]
138-52-3 | [Synonyms]
2-(HYDROXYMETHYL)PHENYL-BETA-D-GLUCOPYRANOSIDE
2-(HYDROXYMETHYL)PHENYL-BETA-D-GLUCOPYYRANOSIDE
2-(HYDROXYMETHYL)PHENYL-BETA-D-GLUCOSIDE
D-(-)-SALICIN
D-SALICIN
SALICIN
SALICOSIDE
SALICYLALCOHOL BETA-D-GLUCOSIDE
SALICYL ALCOHOL GLUCOSIDE
SALICYLALDEHYDE-B-D-GLUCOSIDE
SALIGENIN-B-D-GLUCOSIDE
SALIGENIN-B-D-GLYCOPYRANOSIDE
WHITE WILLOW
2-(Hydroxymethyl)phenyl hexopyranoside
2-(hydroxymethyl)phenyl-beta-d-glucopyranosid
Benzyl alcohol, o-hydroxy-, O-glucoside
beta-D-Glucopyranoside, 2-(hydroxymethyl)phenyl
beta-d-glucopyranoside,2-(hydroxymethyl)phenyl
o-(Hydroxymethyl)phenyl beta-D-glucopyranoside
Salicine | [EINECS(EC#)]
205-331-6 | [Molecular Formula]
C13H18O7 | [MDL Number]
MFCD00006590 | [Molecular Weight]
286.28 | [MOL File]
138-52-3.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystals or powder | [Melting point ]
196-202 °C
| [alpha ]
-61.5 º (c=5, water) | [Boiling point ]
388.65°C (rough estimate) | [density ]
1.4340 | [refractive index ]
-62 ° (C=3, H2O) | [storage temp. ]
Store at RT. | [solubility ]
36g/l | [form ]
Fine Crystalline Powder | [pka]
12.80±0.70(Predicted) | [color ]
White | [Stability:]
Stable, but light sensitive. Incompatible with strong oxidizing agents. | [Water Solubility ]
36 g/L (15 ºC), 250 g/L (60 ºC) | [Detection Methods]
HPLC,NMR | [Merck ]
14,8324 | [BRN ]
89593 | [InChIKey]
NGFMICBWJRZIBI-MICYEWLZSA-N | [LogP]
-1.232 (est) | [CAS DataBase Reference]
138-52-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Salicin(138-52-3) | [EPA Substance Registry System]
138-52-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R43:May cause sensitization by skin contact. | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S37:Wear suitable gloves .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
LZ5901700
| [F ]
3-10 | [TSCA ]
Yes | [HS Code ]
29389090 |
| Questions And Answer | Back Directory | [Description]
D(-)-Salicin is a traditional medicine which has been known to exhibit anti-inflammation and other therapeutic activities, it can inhibit the LPS-induced inflammation in RAW264.7 cells and mouse models. |
| Hazard Information | Back Directory | [Chemical Properties]
white crystals or powder | [Uses]
analgesic, antipyretic | [Uses]
H1 antihistamine (nonsedating) | [Uses]
Standard substrate in evaluating enzyme Preparations contg b-glucosidase: Weidenhagen, Z. Ver. Zucker-Ind. 79, 591 (1929). | [Definition]
ChEBI: An aryl beta-D-glucoside that is the beta-D-glucoside of the phenolic hydroxy group of salicyl alcohol. | [General Description]
Salicin is a non-phenolic glucosidic compound extracted from meadowsweet (Filipendula ulmaria L). It is majorly used as a substitute for quinine. Salicin can be used as a therapeutic for patients suffering from rheumatic fever. Salicin acts a metabolic precursor for salicylic acid. It is a novel phytochemical that exhibits immunological cross functions in plants and humans. Salicin facilitates growth and reproduction in plants. In addition, It also protects plants against biotic and abiotic stress. | [Biochem/physiol Actions]
D-(?)-Salicin exerts anti-rheumatism and anti-inflammatory activities. It inhibits lipopolysaccharide (LPS) induced inflammation in in vitro and in vivo studies. It regulates different signaling pathways such as nuclear factor kappa B (NF-κB) and mitogen-activated protein kinase (MAPK). It also regulates cytokines concentration such as tumor necrosis factor-alpha(TNF-α), interleukin-1β, interleukin-6, and interleukin-10. | [Synthesis]
GENERAL METHODS: The compound (CAS:16643-37-1) was used as raw material and mixed with the acceptor ArOH (3.0 eq.) in anhydrous DCM (0.1 M), to which was added freshly prepared BF3-OEt2 solution (1.0 eq., 1 M, in anhydrous DCM). The reaction mixture was stirred at room temperature for 1 h. Subsequently, the progress of the reaction was monitored by TLC (30:70; EtOAc: hexane). Upon completion of the reaction, the reaction was quenched by the addition of NaHCO3 (aqueous), the mixture was extracted with DCM, the organic phase was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuum. The α/β ratio of the crude product was analyzed by 1H NMR. The residue was dissolved in anhydrous methanol (0.3 M) and freshly prepared MeONa solution (0.25 equiv., 0.5 M methanol solution) was added and stirred for 1 h at room temperature. The reaction mixture was neutralized with Amberlite IR-120H+ , filtered and concentrated in vacuum to give a white solid. Purification by fast column chromatography (10:90; MeOH:DCM) removes excess ArOH to give β-D isoheads, which are finally recrystallized in hot ethanol. | [storage]
Store at -20°C | [Purification Methods]
Crystallise D(-)-salicin from EtOAc, EtOH or water and sublime it at 190-195o/12mm. [Armour et al. J Chem Soc 412 1961, IR: Pearl & Darling J Org Chem 24 731 1959, Beilstein 17 III/IV 2986, 17/7 V 113.] | [References]
[1] Synthesis (Germany), 2016, vol. 48, # 20, p. 3575 - 3588 |
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