gastrodin
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(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol (Click)
CAS Number: 62499-27-8
FDA UNII: 5YS9U2W3RQ
MDL: MFCD00272169
XlogP3: -0.80 (est)
Molecular Weight: 286.28086000
Formula: C13 H18 O7
BioActivity Summary: listing
NMR Predictor: Predict
Category: cosmetic agents
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 563.20 °C. @ 760.00 mm Hg (est)
Flash Point: 562.00 °F. TCC ( 294.40 °C. ) (est)
logP (o/w): -1.939 (est)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: skin conditioning
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Suppliers:
Carbosynth
Gastrodin
For experimental / research use only.
Changsha Organic Herb
Gastrodin Gastrodia Tuber Extract
Coompo
Gastrodin from Plants ≥98%
Odor: characteristic
Use: Phenolic glucoside gastrodin (Gas), which is a main component extracted from the Chinese herbs Gastrodia elata Bl, is a well-known natural calcium antagonist with antioxidant and anti-inflammatory functions. It has long been used clinically for treatment of cardiovascular and cerebrovascular diseases. Previous studies have shown that gastrodin possesses comprehensive pharmacological functions. However, very little is known about whether gastrodin has protective role on cardiac hypertrophy. The aim of this study was to determine whether gastrodin attenuates pressure overload-induced cardiac hypertrophy in mice and to clarify the underlying molecular mechanisms. Our data demonstrated that gastrodin prevented cardiac hypertrophy induced by aortic banding (AB), as assessed by heart weight/body weight and lung weight/body weight ratios, echocardiographic parameters, and gene expression of hypertrophic markers. The inhibitory effect of gastrodin on cardiac hypertrophy is mediated by ERK1/2 signaling and GATA-4 activation. Further studies showed that gastrodin attenuated fibrosis and collagen synthesis through abrogating ERK1/2 signaling pathway. Therefore, these findings indicated that gastrodin, which is a potentially safe and inexpensive therapy for clinical use, has protective potential in targeting cardiac hypertrophy and fibrosis through suppression of ERK1/2 signaling. Gastrodin significantly attenuate levels of neurotoxic proinflammatory mediators and proinflammatory cytokines by inhibition of the NF-?B signaling pathway and phosphorylation of MAPKs in LPS-stimulated microglial cells. Arising from the above, we suggest that gastrodin has a potential as an anti-inflammatory drug candidate in neurodegenerative diseases. Gastrodin is an effective and a safe drug for the prevention of neurocognitive decline in patients undergoing mitral valve replacement surgery with CPB.
For experimental / research use only.
Dalton Pharma Services
Gastrodin >95%
For experimental / research use only.
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
  Not determined
Dermal Toxicity:
  Not determined
Inhalation Toxicity:
  Not determined
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Safety in Use Information:
Category: cosmetic agents
Recommendation for gastrodin usage levels up to:
 not for fragrance use.
Recommendation for gastrodin flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Chemicalize.org: Calculate predicted properties
Toxicology Citations: Search
EPA ACToR: Toxicology Data
National Institute of Allergy and Infectious Diseases: Data
 (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
Chemidplus: 0062499278
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References:
 (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 115067
Pubchem (sid): 135072124
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEMBL: View
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
None Found
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Potential Uses:
None Found
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Natural Occurrence in: note
 gastrodia elata root
GRIN Trop Picture
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Synonyms:
 gastrodine
beta-D-glucopyranoside, 4-(hydroxymethyl)phenyl
4-(beta-D-glucopyranosyloxy) benzyl alcohol
(2R,3S,4S,5R,6S)-2-hydroxymethyl-6-(4-hydroxymethyl-phenoxy)-tetrahydro-pyran-3,4,5-triol
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-(hydroxymethyl)phenoxy)-tetrahydro-2H-pyran-3,4,5-triol
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-(hydroxymethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triol
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
4-(hydroxymethyl)phenyl b-D-glucopyranoside
4-(hydroxymethyl)phenyl-beta-D-glucopyranoside
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Articles:
PubMed: Two new neuroprotective phenolic compounds from Gastrodia elata.
PubMed: [Chemical constituents from aqueous extract of Gastrodia elata].
PubMed: [In vivo transmigration of active ingredients from Gastrodia elata in dachuanxiong fang].
PubMed: Pharmacokinetics comparative study of a novel Chinese traditional herbal formula and its compatibility.
PubMed: [Constituents of Gymnadenia conopsea].
PubMed: Gastrodin prevents motor deficits and oxidative stress in the MPTP mouse model of Parkinson's disease: Involvement of ERK1/2-Nrf2 signaling pathway.
PubMed: H nuclear magnetic resonance-based metabolomics reveals sex-specific metabolic changes of gastrodin intervention in rats.
PubMed: Analysis and pharmacokinetics studies of gastrodin and p-hydroxybenzyl alcohol in dogs using ultra fast liquid chromatography-tandem mass spectrometry method.
PubMed: Prescription pattern of Chinese herbal products for hypertension in Taiwan: A population-based study.
PubMed: Identification and analysis of gastrodin and its five metabolites using ultra fast liquid chromatography electrospray ionization tandem mass spectrometry to investigate influence of multiple-dose and food.
PubMed: [Chemical constituents from whole plants of Aconitum tanguticum (III)].
PubMed: Gastrodin protects against MPP(+)-induced oxidative stress by up regulates heme oxygenase-1 expression through p38 MAPK/Nrf2 pathway in human dopaminergic cells.
PubMed: Gastrodin ameliorates memory deficits in 3,3'-iminodipropionitrile-induced rats: possible involvement of dopaminergic system.
PubMed: Molecularly imprinted polymers with novel functional monomer for selective solid-phase extraction of gastrodin from the aqueous extract of Gastrodia elata.
PubMed: Gastrodin alleviates memory deficits and reduces neuropathology in a mouse model of Alzheimer's disease.
PubMed: Gastrodin inhibits the activity of acid-sensing ion channels in rat primary sensory neurons.
PubMed: Gastrodin inhibits glutamate-induced apoptosis of PC12 cells via inhibition of CaMKII/ASK-1/p38 MAPK/p53 signaling cascade.
PubMed: Gastrodin ameliorates depression-like behaviors and up-regulates proliferation of hippocampal-derived neural stem cells in rats: involvement of its anti-inflammatory action.
PubMed: Gastrodin ameliorates depressive-like behaviors and up-regulates the expression of BDNF in the hippocampus and hippocampal-derived astrocyte of rats.
PubMed: Gastrodin ameliorates anxiety-like behaviors and inhibits IL-1beta level and p38 MAPK phosphorylation of hippocampus in the rat model of posttraumatic stress disorder.
PubMed: [Eighty-seven cases of vertigo treated by acupuncture and acupoint injection of gastrodin].
PubMed: Phenanthrenes, 9,10-dihydrophenanthrenes, bibenzyls with their derivatives, and malate or tartrate benzyl ester glucosides from tubers of Cremastra appendiculata.
PubMed: Elution-extrusion counter-current chromatography separation of two new benzyl ester glucosides and three other high-polarity compounds from the tubers of Pleione bulbocodioides.
PubMed: Gastrodin ameliorates Parkinson's disease by downregulating connexin 43.
PubMed: Two new neuroprotective phenolic compounds from Gastrodia elata.
PubMed: [Chemical constituents from Pleione bulbocodioides].
PubMed: [Research the extraction and detection method of gastrodin content in Gastrodia elata].
PubMed: The characteristics of open-tubular capillary electrochromatography columns with series/mixed stationary phases constructed with magnetic nanoparticle coating.
PubMed: Gastrodin stimulates anticancer immune response and represses transplanted H22 hepatic ascitic tumor cell growth: Involvement of NF-κB signaling activation in CD4+ T cells.
PubMed: Gastrodin protects apoptotic dopaminergic neurons in a toxin-induced Parkinson's disease model.
PubMed: Synthesis and anti-influenza virus activities of a novel class of gastrodin derivatives.
PubMed: Gastrodin production from p-2-hydroxybenzyl alcohol through biotransformation by cultured cells of Aspergillus foetidus and Penicillium cyclopium.
PubMed: Role of glucose transporters in the intestinal absorption of gastrodin, a highly water-soluble drug with good oral bioavailability.
PubMed: Experimental analysis on the main contents of Rhizoma gastrodiae extract and inter-transformation throughout the fermentation process of Grifola frondosa.
PubMed: Gastrodin attenuation of the inflammatory response in H9c2 cardiomyocytes involves inhibition of NF-κB and MAPKs activation via the phosphatidylinositol 3-kinase signaling.
PubMed: Simultaneous determination of gastrodin and puerarin in rat plasma by HPLC and the application to their interaction on pharmacokinetics.
PubMed: [Chemical constituents from aqueous extract of Gastrodia elata].
PubMed: Gastrodin protect primary cultured rat hippocampal neurons against amyloid-beta peptide-induced neurotoxicity via ERK1/2-Nrf2 pathway.
PubMed: Gastrodin inhibits cell proliferation in vascular smooth muscle cells and attenuates neointima formation in vivo.
PubMed: Gastrodin improved baroreflex sensitivity and increased gamma-amino butyric acid content in brains without decreasing blood pressure in spontaneously hypertensive rats.
PubMed: Gastrodin inhibits allodynia and hyperalgesia in painful diabetic neuropathy rats by decreasing excitability of nociceptive primary sensory neurons.
PubMed: [The pharmacological mechanism of gastrodin on calcitonin gene-related peptide of cultured rat trigeminal ganglion].
PubMed: Gastrodia elata Blume and its pure compounds protect BV-2 microglial-derived cell lines against β-amyloid: the involvement of GRP78 and CHOP.
PubMed: Identification of three novel polyphenolic compounds, origanine A-C, with unique skeleton from Origanum vulgare L. using the hyphenated LC-DAD-SPE-NMR/MS methods.
PubMed: Formulation and evaluation of in situ gelling systems for intranasal administration of gastrodin.
PubMed: [In vivo transmigration of active ingredients from Gastrodia elata in dachuanxiong fang].
PubMed: Gastrodin protects against cardiac hypertrophy and fibrosis.
PubMed: Gastrodin inhibits expression of inducible NO synthase, cyclooxygenase-2 and proinflammatory cytokines in cultured LPS-stimulated microglia via MAPK pathways.
PubMed: Pharmacokinetics comparative study of a novel Chinese traditional herbal formula and its compatibility.
PubMed: [Pharmacokinetics of gastrodin from compound Tianma granule in rats].
PubMed: Inhibitors of microglial neurotoxicity: focus on natural products.
PubMed: The transport of gastrodin in Caco-2 cells and uptake in Bcap37 and Bcap37/MDR1 cells.
PubMed: [Constituents of Gymnadenia conopsea].
PubMed: Enzymic synthesis of gastrodin through microbial transformation and purification of gastrodin biosynthesis enzyme.
PubMed: Neuroprotective effect of honokiol and magnolol, compounds from Magnolia officinalis, on beta-amyloid-induced toxicity in PC12 cells.
PubMed: Determination and pharmacokinetics of gastrodin in human plasma by HPLC coupled with photodiode array detector.
PubMed: [The effect of gastrodine on hepatitic cell line L02 injury induced by ethanol].
PubMed: [Simultaneous determination of four components in Gastrodia elata by RP-HPLC].
PubMed: Effects of gastrodin on the dopamine system of Tourette's syndrome rat models.
PubMed: [Study on the preparation of sustained-release pellets containing active components from Gastrodia elata by fluid-bed coating].
PubMed: [The determination of three effective constituents in wild and cultivated Gastrodia elata from Bomi].
PubMed: [Gastrodine represses expression of IL-1 beta, IL-6 induced by hyperglycemia in gitter cells].
PubMed: Protective effects of gastrodin on lead-induced synaptic plasticity deficits in rat hippocampus.
PubMed: Relationships among genetic makeup, active ingredient content, and place of origin of the medicinal plant Gastrodia tuber.
PubMed: Pharmacokinetics of gastrodin and its metabolite p-hydroxybenzyl alcohol in rat blood, brain and bile by microdialysis coupled to LC-MS/MS.
PubMed: [Expression of NR1 mRNA of NMDA receptor by gastrodine on hypoxia injury in cultured rat cerebral cortical neurons].
PubMed: [Effects of gastrodin injection on blood pressure and vasoactive substances in treatment of old patients with refractory hypertension: a randomized controlled trial].
PubMed: [Study on drug release of gastrodin ion-activated nasal in situ gel in vitro].
PubMed: [Brain targeting of gastrodin nasal in situ gel].
PubMed: [Chemical constituents from the tuber of Cremastra appendiculata].
PubMed: Determination and pharmacokinetics of gastrodin and p-hydroxybenzylalcohol after oral administration of Gastrodia elata Bl. extract in rats by high-performance liquid chromatography-electrospray ionization mass spectrometric method.
PubMed: Effect of borneol on the distribution of gastrodin to the brain in mice via oral administration.
PubMed: Evaluation of the extraction efficiency of thermally labile bioactive compounds in Gastrodia elata Blume by pressurized hot water extraction and microwave-assisted extraction.
PubMed: Distribution and metabolism of gastrodin in rat brain.
PubMed: Two new benzofurans from Gastrodia elata and their DNA topoisomerases I and II inhibitory activities.
PubMed: [Study on extraction and purification of active parts from Da Chuan Xiong Fang for treatment of migraine].
PubMed: [Evaluation of the quality of Gastrodia elata Bl. by HPLC-DAD/MS].
PubMed: Determination of gastrodin and vanillyl alcohol in Gastrodia elata Blume by pressurized liquid extraction at room temperature.
PubMed: Identification of phenolics and nucleoside derivatives in Gastrodia elata by HPLC-UV-MS.
PubMed: Phenolic compounds from the rhizomes of Gastrodia elata.
PubMed: Protective effects of gastrodin on hypoxia-induced toxicity in primary cultures of rat cortical neurons.
PubMed: A hybrid microdevice with a thin PDMS membrane on the detection window for UV absorbance detection.
PubMed: Pharmacokinetics of Gastrodin in rat plasma and CSF after i.n. and i.v.
PubMed: Analysis of brain distribution and biliary excretion of a nutrient supplement, gastrodin, in rat.
PubMed: A microdialysis study of effects of gastrodin on neurochemical changes in the ischemic/reperfused rat cerebral hippocampus.
PubMed: Effects of gastrodin on amino acids after cerebral ischemia-reperfusion injury in rat striatum.
PubMed: Phenolic constituents from the rhizomes of Gastrodia elata.
PubMed: [Synthesis of gastrodin by microbial transformation].
PubMed: [Preparation and stability investigation of gastrodin dispersible tablets].
PubMed: [The production of gastrodin through biotransformation of p-hydroxybenzaldehyde by cell suspension culture of Datura stramonium].
PubMed: A study of the neuroprotective effect of the phenolic glucoside gastrodin during cerebral ischemia in vivo and in vitro.
PubMed: [Production of gastrodin through biotransformation of p-hydroxybenzaldehyde by cell suspension cultures of Datura tatula L].
PubMed: [Cloning of distinguishing DNA sequences of Gastrodia elata Blume and application of them in identifying gastrodia tuber].
PubMed: Gastrodin interaction with human fibrinogen: anticoagulant effects and binding studies.
PubMed: Simultaneous determination of Gastrodin and Ligustrazine hydrochloride in dog plasma by gradient high-performance liquid chromatography.
PubMed: [Protective effects of gastrodin on the cellular model of Alzheimer's disease induced by Abeta25-35].
PubMed: Preparative isolation and purification of gastrodin from the Chinese medicinal plant Gastrodia elata by high-speed counter-current chromatography.
PubMed: Chemical constituents of the rhizomes of Coeloglossum viride var. bracteatum.
PubMed: [Studies on chemical constituents from Tibetan medicine wangla(rhizome of Coeloglossum viride var. bracteatum)].
PubMed: [Studies on the chemical constituents of Coeloglossum viride (L.) Hartm. var. bracteatum (Willd.) Richter].
PubMed: [Effect of various nutrient solutions on quality of Gastrodia elata].
PubMed: Gastrodin decreases immunoreactivities of gamma-aminobutyric acid shunt enzymes in the hippocampus of seizure-sensitive gerbils.
PubMed: [Analysis gastrodin in various types of Gastrodia elata Bl].
PubMed: Determination of the active ingredients in Gastrodia rhizoma by capillary electrophoresis with electrochemical detection.
PubMed: Isolation and identification of succinic semialdehyde dehydrogenase inhibitory compound from the rhizome of Gastrodia elata Blume.
PubMed: [The effect of Tianma injection on cultured vascular smooth muscle cells proliferation].
PubMed: Gastrodin and p-hydroxybenzyl alcohol facilitate memory consolidation and retrieval, but not acquisition, on the passive avoidance task in rats.
PubMed: Effects of Gastrodia elata and its active constituents on scopolamine-induced amnesia in rats.
PubMed: [Quantitative method for the determination of contents of gastrodin in zhennaonin capsules].
PubMed: p-Hydroxybenzyl alcohol attenuates learning deficits in the inhibitory avoidance task: involvement of serotonergic and dopaminergic systems.
PubMed: Hearing loss and trace elements Fe2+ and Zn2+ in the perilymph.
PubMed: [Biodistribution and metabolism of 3H-gastrodigenin and 3H-gastrodin in mice].
PubMed: [The effect of different types of premedication on gastric juice volume and pH].
PubMed: [Studies on the phenolic derivatives from Galeola faberi Rolfe].
PubMed: [Study of the mechanism of gastrodin and derivatives of gastrodigenin].
PubMed: [A trial of utilizing TDP (specific electromagnetic wave) in cultivating Gastrodia elata Bl].
PubMed: [Comparison studies on pharmacological properties of injectio gastrodia elata, gastrodin-free fraction and gastrodin].
PubMed: [The distribution of 3H-alpha-sec-butyl-p hydroxybenzyl alcohol in mice].
PubMed: [Studies on the quality of Gastrodia elata Bl. cultivated with various kinds of fungus-growing materials].
PubMed: [Effect of sapogenins from the leaves of Panax notoginseng on migraine].
PubMed: [Determination of gastrodin in biological specimens and in pharmacokinetics].
PubMed: Simultaneous determination of gastrodin and its metabolite by HPLC.
PubMed: [Study on the stability of gastrodin injection].
PubMed: [Effect of synthetic gastrodin on the beating and histochemical changes of cultured heart cells of neonatal rats].
PubMed: [Circadian effect on gastrodin pharmacokinetics in rats].
PubMed: [Processing of Gastrodia elata where it is produced].
PubMed: [Studies on some pharmacological effects of gastrodia injection and gastrodin].
PubMed: [Effect of synthetic gastrodin in an injectable form on neurasthenia].
PubMed: [Recent developments in pharmacological study and clinical application of Gastrodia elata in China].
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Soluble in:
 water, 2.38e+005 mg/L @ 25 °C (est)
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