Gastrodin

Title: Gastrodin
CAS Registry Number: 62499-27-8
CAS Name: 4-(Hydroxymethyl)phenyl-b-D-glucopyranoside
Additional Names: 4-(b-D-glucopyranosyloxy)benzyl alcohol
Molecular Formula: C13H18O7
Molecular Weight: 286.28
Percent Composition: C 54.54%, H 6.34%, O 39.12%
Literature References: Pharmacologically active constituent of the traditional medicinal plant, gastrodia, q.v. Prepn: B. Helferich et al., Ann. 508, 192 (1934); A. E. Pavlov et al., Russ. J. Gen. Chem. 71, 1811 (2001). Isoln from Gastrodia elata tuber: H. Taguchi et al., Chem. Pharm. Bull. 29, 55 (1981); H.-B. Li, F. Chen, J. Chromatogr. A 1052, 229 (2004). CE determn in medicinal formulations: Y. Zhao et al., ibid. 849, 277 (1999). Pharmacokinetics in rats: R. Wang et al., J. Liq. Chromatogr. Relat. Technol. 25, 857 (2002). Pharmacology in gerbils: S.-J. An et al., J. Neurosci. Res. 71, 534 (2003).
Properties: mp 169-170°. [a]D20 -17.5° (c = 1 in pyridine). pKa 9.10. uv max (aq soln): 249 nm (log e 4.140).
Melting point: mp 169-170°
pKa: pKa 9.10
Optical Rotation: [a]D20 -17.5° (c = 1 in pyridine)
Absorption maximum: uv max (aq soln): 249 nm (log e 4.140)
Derivative Type: Hemihydrate
Properties: Colorless needles from methanol + ethyl acetate, mp 156-157°. [a]D33 -62.1° (in ethanol). uv max (ethanol): 223, 273, 278 (log e 3.91, 2.88, sh 2.78).
Melting point: mp 156-157°
Optical Rotation: [a]D33 -62.1° (in ethanol)
Absorption maximum: uv max (ethanol): 223, 273, 278 (log e 3.91, 2.88, sh 2.78)
Gatifloxacin Gaultherin GDNF Gefarnate Geissoschizoline

Gastrodin
Chemical structure of gastrodin
Identifiers
CAS number 62499-27-8 YesY
PubChem 115067
ChemSpider 102977 N
Jmol-3D images Image 1
Properties
Molecular formula C13H18O7
Molar mass 286.27 g/mol
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Gastrodin is a natural phenol. It is the glucoside of 4-hydroxybenzyl alcohol (gastrodigenin). It can be isolated from the orchids Gastrodia elata or from the rhizome of Galeola faberi.[1]

It can also be produced by biotransformation of 4-hydroxybenzaldehyde by Datura tatula cell cultures.[2]