D-(-)-Salicin CAS 138-52-3
D-(-)-Salicin Basic informationDescription
| Product Name: | D-(-)-Salicin |
| Synonyms: | D-(-)-SALICIN;D-SALICIN;2-(HYDROXYMETHYL)PHENYL-BETA-D-GLUCOPYRANOSIDE;2-(HYDROXYMETHYL)PHENYL-BETA-D-GLUCOPYYRANOSIDE;2-(HYDROXYMETHYL)PHENYL-BETA-D-GLUCOSIDE;2-(Hydroxymethyl)phenyl hexopyranoside;SALICYLALDEHYDE-B-D-GLUCOSIDE;SALICYLALCOHOL BETA-D-GLUCOSIDE |
| CAS: | 138-52-3 |
| MF: | C13H18O7 |
| MW: | 286.28 |
| EINECS: | 205-331-6 |
| Product Categories: | chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Plant extract;Herbs & Natural Remedies;Sugars, Carbohydrates & Glucosides;Biochemistry;Glucose;Glycosides;Sugars;Natural Plant Extract;HISMANAL;carbohydrate;Inhibitors |
| Mol File: | 138-52-3.mol |
D-(-)-Salicin Chemical Properties
| 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. | 2-8°C |
| solubility | 36g/l |
| pka | 12.80±0.70(Predicted) |
| form | Fine Crystalline Powder |
| color | White |
| Water Solubility | 36 g/L (15 ºC), 250 g/L (60 ºC) |
| Merck | 14,8324 |
| BRN | 89593 |
| Stability: | Stable, but light sensitive. Incompatible with strong oxidizing agents. |
| Major Application | cleaning products cosmetics flavors and fragrances food and beverages personal care |
| Cosmetics Ingredients Functions | SKIN CONDITIONING |
| InChI | 1S/C13H18O7/c14-5-7-3-1-2-4-8(7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1 |
| InChIKey | NGFMICBWJRZIBI-MICYEWLZSA-N |
| SMILES | OC[C@H]1O[C@@H](Oc2ccccc2CO)[C@H](O)[C@@H](O)[C@@H]1O |
| LogP | -1.232 (est) |
| CAS DataBase Reference | 138-52-3(CAS DataBase Reference) |
| NIST Chemistry Reference | Salicin(138-52-3) |
| EPA Substance Registry System | .beta.-D-Glucopyranoside, 2-(hydroxymethyl)phenyl (138-52-3) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 43 |
| Safety Statements | 36/37-37-24/25-36 |
| WGK Germany | 3 |
| RTECS | LZ5901700 |
| F | 3-10 |
| TSCA | TSCA listed |
| HS Code | 29389090 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Skin Sens. 1 |
| 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. |
| Chemical Properties | white crystals or powder |
| Uses | analgesic, antipyretic |
| Uses | H1 antihistamine (nonsedating) |
| Uses | D-(-)-Salicin has been used:
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| 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 | 16643-37-1 138-52-3 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. |
| 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 |
D-(-)-Salicin Preparation Products And Raw materials
| Raw materials | 2-[(Acetyloxy)methyl]phenyl β-D-glucopyranoside 2,3,4,6-tetraacetate-->Willow Bark Extract-->Sodium Methoxide-->Methanol |
