Gastrodin

Base Information

• Chemical Name: Gastrodin
• CAS No.: 62499-27-8
• Molecular Formula: C₁₃H₁₈O₇
• Molecular Weight: 286.282
• Hs Code.: 29329990
• European Community (EC) Number: 683-202-7
• UNII: 5YS9U2W3RQ
• DSSTox Substance ID: DTXSID30978086
• Nikkaji Number: J39.391F
• Wikipedia: Gastrodin
• Wikidata: Q5526833
• Metabolomics Workbench ID: 129992
• ChEMBL ID: CHEMBL274739
• Mol file: 62499-27-8.mol

Synonyms:gastrodin;gastrodine

Chemical Property of Gastrodin

Chemical Property:

• Appearance/Colour: White crystal.
• Vapor Pressure: 1.6E-13mmHg at 25°C
• Melting Point: 154-157oC
• Refractive Index: 1.638
• Boiling Point: 563.2 °C at 760 mmHg
• PKA: 9.10(at 25℃)
• Flash Point: 294.4 °C
• PSA: 119.61000
• Density: 1.504 g/cm³
• LogP: -1.64240
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly, Sonicated), Methanol (Slightly), Water (Slightly, Sonicated)
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 286.10525291
• Heavy Atom Count: 20
• Complexity: 292

Purity/Quality:

99% ^*data from raw suppliers

Gastrodin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CO)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1CO)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Description: Gastrodin is extracted from the dry root of the orchid plant, Gastrodia elata. The source of raw materials is Yunnan Province. Traditional Chinese medicine Gastrodia elata (Gastrodia elata Bl.) is also known as Chi Jian, Ding Feng Cao, Shui Yang Yu, and so on, belonging to special symbiosis perennial herb of Orchidaceae and Armillaria mellea. The medicinal part is its tubers. It has sweet flavor and liver channel tropism and is neutral in nature. Traditional Chinese medicine believes that its main functions are to expel wind and relieve convulsion, calm the liver and suppress liver-yang, and expel wind evil and channel. There are 23 chemical ingredients extracted from Gastrodia elata, including gastrodin, gastrodia glycosides, vanilla alcohol, vanilla aldehyde, beta steroid valley alcohol, p-hydroxybenzoic acid, carrot glycosides, and so on, among which the highest content of single active ingredient is Gastrodia glycosides, namely, gastrodin
• Physical properties: Appearance: white prismatic crystal, odorless, and bitter; little hygroscopicity. Solubility: soluble in water, methanol, ethanol, acetone, and acetonyl acetate, insoluble in chloroform, and poorly soluble in ethyl ether. Melting point: ?153 to 156?°C. Specific optical rotation: ?68 to ?72° .
• Uses: Gastrodin up regulates heme oxygenase-1 expression through activation of p38 MAPK/Nrf2 signaling pathway thus protecting the SH-SY5Y cells from MPP+-induced oxidative cell death.
• Indications: Gastrodin is included in the International Pharmacopoeia (5th ed.). The dosage forms include injections, tablets, and capsules. They are widely used for the treatment of vertigo (Meniere’s disease, medicinal dizziness, traumatic vertigo, sudden deafness, vestibular neuronitis, vertebrobasilar insufficiency, etc.), headache (vascular headache, migraine, etc.), neuralgia (trigeminal neuralgia, sciatica, etc.), neurasthenia syndrome, and brain traumatic syndrome .
• Clinical Use: Gastrodin has sedative and hypnotic, analgesia, and immune enhancement function and is used for the treatment of tension headache to relieve pain and intense sentiment and thus further relieve the related symptoms . Clinical usage of gastrodin acupoint injection to treat insomnia also achieves certain effect . Moreover, gastrodin agents have been used for the treatment of cardiovascular diseases and microcirculation system, such as hypertension and coronary heart disease without obvious side effects .It is also reported that gastrodin can treat epilepsy, vascular dementia, deafness, tinnitus, herpes zoster, osteoarthritis, cognitive impairment, and so on but still needs further investigation.

Technology Process of Gastrodin

There total 35 articles about Gastrodin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.5%

4-(tetra-O-acetyl-β-D-glucopyranosyloxy)benzyl acetate (59252-47-0) → gastrodin (62499-27-8,106982-96-1)

Guidance literature:

With sodium methylate; In methanol; for 4h; Reflux;

Reference yield: 96.2%

4-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (2887-07-2,31873-42-4,148579-45-7) → gastrodin (62499-27-8,106982-96-1)

Guidance literature:

With sodium tetrahydroborate; sodium methylate; In methanol; at 50 ℃;

Reference yield: 93.03%

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(hydroxymethyl)phenoxy)-tetrahydro-2H-pyran-3,4,5-triyl triacetate (64291-41-4,105054-56-6) → gastrodin (62499-27-8,106982-96-1)

Guidance literature:

With potassium hydroxide; In ethanol; for 4h; pH=9; Reagent/catalyst; pH-value; Reflux;

upstream raw materials:

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(hydroxymethyl)phenoxy)-tetrahydro-2H-pyran-3,4,5-triyl triacetate

(4-hydroxyphenyl)methanol

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

4-(bromomethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Downstream raw materials:

4-(tetra-O-acetyl-β-D-glucopyranosyloxy)benzyl acetate

C₁₃H₁₇ClO₆

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(hydroxymethyl)phenoxy)-tetrahydro-2H-pyran-3,4,5-triyl triacetate

(4-hydroxyphenyl)methanol

Refernces

• 1、 -. "Synthesis method and application of gastrodin semihydrate". Paragraph 0066-0088. . Retrieved 2020/05/01.
• 2、 Li, Yun,Liu, Xiao-Qian,Liu, Shan-Shan,Liu, Da-hui,Wang, Xiao,Wang, Zhi-Min. "Transformation mechanisms of chemical ingredients in steaming process of gastrodia elata blume". . . Retrieved 2019/09/06.