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

• ChemBase ID: 73007
• Molecular Formular: C13H18O7
• Molecular Mass: 286.27782
• Monoisotopic Mass: 286.10525292
• SMILES: [C@@H]1([C@@H]([C@H]([C@@H](O[C@@H]1CO)Oc1ccc(cc1)CO)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2)CO)[C@@H]([C@H]([C@@H]1O)O)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol; gastrodin
• Synonyms: Gastrodine; Gastrodin(Gastrodine); 4-(beta-D-glucopyranosyloxy) benzyl alcohol; Gastrodin; (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-(hydroxymethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triol; 4-Hydroxybenzyl alcohol; 4-O-beta-D-Glucopyranoside; 4-(Hydroxymethyl)phenyl beta- D -glucopyranoside; 4-beta- D Glucopyranosyloxybenzyl alcohol; Gastrodin

Database IDs

• CAS Number: 62499-27-8
• PubChem SID: 162037927
• PubChem CID: 115067
• Chemspider ID: 102977
• Wikipedia Title: Gastrodin

CALCULATED PROPERTIES

• Acid pKa: 12.199467
• 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: 27.105778 Å^3
• Polar Surface Area: 119.61 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Mechanism of Action: Increases extracellular glutamate level; Prevents glutamate- and NMDA-induced neurotoxicity

Product Information

• Salt Data: Free Base
• Biological Source: Isol. from Gastrodia elata and Galeolae septentrionalis
• Application(s): Anticonvulsant; Antihypertensive; Hypnotic and Sedative props.

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, ,

REFERENCES

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• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 352B; 352C; 353B, (nmr)
• Aldrich Library of FT-IR Spectra: Vapor Phase, 1989, 3, 1059C; 1059D, (ir)
• Spth, E., Monatsh. Chem., 1914, 35, 319, (synth)
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• Taguchi, H. et al., Chem. Pharm. Bull., 1981, 29, 55, (Gastrodin)
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• Lewis, R.J., Food Additives Handbook, Van Nostrand Reinhold International, New York, 1989, MED500
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