(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol

• ChemBase ID: 72977
• Molecular Formular: C13H18O7
• Molecular Mass: 286.27782
• Monoisotopic Mass: 286.10525292
• SMILES: [C@H]1([C@H]([C@@H]([C@H]([C@@H](O1)Oc1ccccc1CO)O)O)O)CO
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccccc2CO)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: 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-UJPOAAIJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
• IUPAC Traditional name: salicin; (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
• Synonyms: Salicoside; Salicine; Salicin; 2-(Hydroxymethyl)phenyl-β-D-glucopyranoside; D-(-)-Salicin; Saligenin glucoside; Salicin; (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-(hydroxymethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triol; D-(-)-水杨苷

Database IDs

• CAS Number: 138-52-3
• EC Number: 205-331-6
• MDL Number: MFCD00006590
• Beilstein Number: 89593
• Merck Index: 148324
• PubChem SID: 162037897; 24899442
• PubChem CID: 439503

CALCULATED PROPERTIES

• Acid pKa: 12.19871
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -1.3657374
• LogD (pH = 7.4): -1.3657442
• Log P: -1.3657373
• Molar Refractivity: 66.9992 cm^3
• Polarizability: 27.106068 Å^3
• Polar Surface Area: 119.61 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder
• Melting Point: 196-202 °C; 200-203°C
• Optical Rotation: [α]20/D -62.5±2°, c = 3% in H2O; -62.5 (c=3 in water)

Safety Information

• Storage Condition: -20°C
• RTECS: LZ5901700
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 43
• Safety Statements: 36/37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Mechanism of Action: Precousor of aspirine via methabolism

Product Information

• Purity: ≥99% (GC); ≥99.0% (TLC); 98%; 99%
• Salt Data: Free Base
• Biological Source: Glucoside of poplar and willow bark
• Application(s): Analgesic; Antipyretic; Antirheumatic agent
• Empirical Formula (Hill Notation): C13H18O7

DETAILS

Selleck Chemicals - S2351

Research Area: Inflammation
Biological Activity:
Salicin(Salicoside, Salicine) is an alcoholic β-glycoside that contains D-glucose. Salicin is an anti-inflammatory agent that is produced from willow bark. Salicin is closely related in chemical make-up to aspirin. When consumed, it is metabolized to salicylic acid. [1]

Sigma Aldrich - S0625

包装
5, 25, 100 g in poly bottle

Sigma Aldrich - 84150

Other Notes
Substrate for β-glucosidase1

REFERENCES

• http://en.wikipedia.org/wiki/Salicin
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 1160D, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 404C, (nmr)
• Irvine, J.C., J.C.S., 1906, 89, 814, (isol)
• Zempln, G., Ber., 1925, 58, 1406, (synth)
• Kunz, A., J.A.C.S., 1926, 48, 262, (synth)
• Richtinger, K. et al., J.A.C.S., 1934, 56, 2495, (isol)
• Thieme, H., Naturwissenschaften, 1963, 50, 477, (synth)
• Steele, W. et al., J. Chromatogr., 1972, 71, 435, (isol)
• Substrate for ? -glucosidase.