4375. Gastrodin

Nomenclature

CAS number: 62499-27-8
4-(Hydroxymethyl)phenyl-β-d-glucopyranoside; 4-(β-d-glucopyranosyloxy)benzyl alcohol.
C13H18O7; mol wt 286.28.
C 54.54%, H 6.34%, O 39.12%.

Description and 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).

Chemical structure

Properties

mp 169-170°. [α]D20 17.5° (c = 1 in pyridine). pKa 9.10. uv max (aq soln): 249 nm (log ε 4.140).

Derivative

Hemihydrate.

Properties

Colorless needles from methanol + ethyl acetate, mp 156-157°. [α]D33 62.1° (in ethanol). uv max (ethanol): 223, 273, 278 (log ε 3.91, 2.88, sh 2.78).