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138-52-3 molecular structure
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(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 and InChIs

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

Cite this record

CBID:72977 http://www.chembase.cn/molecule-72977.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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

CALCULATED PROPERTIES

JChem
Acid pKa 12.19871  H Acceptors
H Donor LogD (pH = 5.5) -1.3657374 
LogD (pH = 7.4) -1.3657442  Log P -1.3657373 
Molar Refractivity 66.9992 cm3 Polarizability 27.106068 Å3
Polar Surface Area 119.61 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Apperance
Powder expand Show data source
Melting Point
196-202 °C expand Show data source
200-203°C expand Show data source
Optical Rotation
[α]20/D -62.5±2°, c = 3% in H2O expand Show data source
-62.5 (c=3 in water) expand Show data source
Storage Condition
-20°C expand Show data source
RTECS
LZ5901700 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
43 expand Show data source
Safety Statements
36/37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H317 expand Show data source
GHS Precautionary statements
P280 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Mechanism of Action
Precousor of aspirine via methabolism expand Show data source
Purity
≥99% (GC) expand Show data source
≥99.0% (TLC) expand Show data source
98% expand Show data source
99% expand Show data source
Salt Data
Free Base expand Show data source
Biological Source
Glucoside of poplar and willow bark expand Show data source
Application(s)
Analgesic expand Show data source
Antipyretic expand Show data source
Antirheumatic agent expand Show data source
Empirical Formula (Hill Notation)
C13H18O7 expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
Selleck Chemicals - S2351 external link
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 external link
包装
5, 25, 100 g in poly bottle
Sigma Aldrich - 84150 external link
Other Notes
Substrate for β-glucosidase1

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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.
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PATENTS

PATENTS

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INTERNET

INTERNET

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