CAS 62499-27-8|Gastrodine|Gastrodin(Gastrodine)|(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol|(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-...

General Information

Structure

Molecular Formula

C₁₃H₁₈O₇

Molecular Mass

286.27782

Exact Mass

286.10525292

Charge

InChI

InChI=1S/C13H18O7/c14-5-7-1-3-8(4-2-7)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

PUQSUZTXKPLAPR-UJPOAAIJSA-N

Canonic Smiles

OC[C@H]1O[C@@H](Oc2ccc(cc2)CO)[C@@H]([C@H]([C@@H]1O)O)O

Isomeric Smiles

[C@@H]1([C@@H]([C@H]([C@@H](O[C@@H]1CO)Oc1ccc(cc1)CO)O)O)O

Calculated Properties

JChem

Acid pKa

12.199467

H Acceptors

H Donor

LogD (pH = 5.5)

-1.3657374

LogD (pH = 7.4)

-1.3657442

Log P

-1.3657373

Molar Refractivity

66.9992

Polarizability

27.105778

Polar Surface Area

119.61

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

GastrodineGastrodin(Gastrodine)(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-(hydroxymethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triol4-(beta-D-glucopyranosyloxy) benzyl alcoholGastrodin4-(Hydroxymethyl)phenyl beta- D -glucopyranosideGastrodin4-beta- D Glucopyranosyloxybenzyl alcohol4-O-beta-D-Glucopyranoside4-Hydroxybenzyl alcohol

IUPAC Traditional name

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

IUPAC name

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

Names and Identifiers

Registration numbers

Wikipedia Title

Chemspider ID

PubChem CID

CAS Number

PubChem SID

Registration numbers

Properties

Safety Information

Storage Condition

-20°C

Product Information

Salt Data

Free Base

Application(s)

Hypnotic and Sedative props.

Antihypertensive

Anticonvulsant

Biological Source

Isol. from Gastrodia elata and Galeolae septentrionalis

Pharmacology Properties

Mechanism of Action

Prevents glutamate- and NMDA-induced neurotoxicity

Increases extracellular glutamate level

Properties

Related Proteins

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Molecular Spectra

No Data Available

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Molecule Details

Selleck Chemicals

S2383

Research Area: Cardiovascular Disease
Biological Activity:
Gastrodin (Gastrodine) is a polyphenol. It is the glucoside of 4-hydroxybenzyl alcohol (gastrodigenin). Gastrodin is the most important and effective ingredient extracted from Chinese natural herbal gastrodia elata B1. Its molecular formula is C13H18O7 and molecular weight is 286.25. Gastrodin could ameliorate cerebral ischemia-reperfusion injury. [1,2] References on Gastrodin (Gastrodine) [1] http://en.wikipedia.org/wiki/Gastrodin, , [2] apjcn.nhri.org.tw/server/APJCN/Volume16/.../XiaodongBie(305-308).pdf, ,

Wikipedia

Gastrodin

Molecule Details

References

PubChem Literature

From Data Sources

• Wang, Q.,G.Chen, et al.(2007).Int J Pharm 341(1-2): 20-25.

• Lewis, R.J., Food Additives Handbook, Van Nostrand Reinhold International, New York, 1989, MED500

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 352B; 352C; 353B, (nmr)

• Inoue, S. et al., Yakugaku Zasshi, 1984, 104, 42, (Gastrodin)

• Taguchi, H. et al., Chem. Pharm. Bull., 1981, 29, 55, (Gastrodin)

• Nakatani, N. et al., Agric. Biol. Chem., 1987, 51, 2727, (synth, Gastrodin)