Gastrodin - analytical standard,Moligand™,≥98% , CAS No.62499-27-8

CAS: 62499-27-8 Cat. No.: G111309 Molecular Weight: 286.28 EC Number: 683-202-7

GRADE & PURITY Analytical standard, Moligand™, ≥98%

Synonyms

NCGC00346601-02_C13H18O7_beta-D-Glucopyranoside, 4-(hydroxymethyl)phenyl | SCHEMBL1076037 | LOPINAVIR [WHO-IP] | AKOS015951256 | BDBM50177403 | Gastrodin, from Gastrodia alata, >=98% | AC-8028 | Gastrodin (Gastrodine) | A833810 | (-)-GASTRODIN | BCP900071

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Gastrodin, a phenolic glucoside, is the main active ingredient of the traditional Chinese medicinal compound Tianma. Gastrodin is an active component of Gastrodia elata Blume, a herb belonging to the Orchidaceae family.

Specifications

Synonyms

NCGC00346601-02_C13H18O7_beta-D-Glucopyranoside, 4-(hydroxymethyl)phenyl | SCHEMBL1076037 | LOPINAVIR [WHO-IP] | AKOS015951256 | BDBM50177403 | Gastrodin, from Gastrodia alata, >=98% | AC-8028 | Gastrodin (Gastrodine) | A833810 | (-)-GASTRODIN | BCP900071

Specifications & Purity

analytical standard, Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Gastrodin can penetrate through the blood-brain barrier and has been suggested to have neuroprotective effects against hypoxia. It is also known to reduce the immunoreactivity of gamma-aminobutyric acid shunt enzymes in hippocampal tissues. Traditionally,

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Analytical standard, Moligand™

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1=CC(=CC=C1CO)OC2C(C(C(C(O2)CO)O)O)O
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
• InChIKey: PUQSUZTXKPLAPR-UJPOAAIJSA-N
• 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
• Isomeric SMILES: C1=CC(=CC=C1CO)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Molecular Weight: 286.28
• Reaxy-Rn: 25441801
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25441801&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 Phenolic glycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: Phenolic glycosides
• Alternative Parents: O-glycosyl compounds Phenoxy compounds Phenol ethers Benzyl alcohols Oxanes Monosaccharides Secondary alcohols Polyols Oxacyclic compounds Acetals Primary alcohols Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenolic glycoside - O-glycosyl compound - Phenoxy compound - Benzyl alcohol - Phenol ether - Monocyclic benzene moiety - Monosaccharide - Oxane - Benzenoid - Secondary alcohol - Polyol - Organoheterocyclic compound - Oxacycle - Acetal - Alcohol - Hydrocarbon derivative - Primary alcohol - Aromatic alcohol - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
• External Descriptors: glycoside

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ABAT Tclin Gamma-amino-N-butyrate transaminase (140 Activities)

Discover Target: ABAT

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH5A1 Tclin Succinate semialdehyde dehydrogenase (19 Activities)

Discover Target: ALDH5A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: heat sensitive
• Specific Rotation[α]: -66.0 to -70.0 deg(C=1,H2O)
• Melt Point(°C): 154-155°C
• Molecular Weight: 286.280 g/mol
• XLogP3: -0.800
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 286.105 Da
• Monoisotopic Mass: 286.105 Da
• Topological Polar Surface Area: 120.000 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 292.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Jiang-Long Shi, Li-Yun Liu, Yu-Ting Dong, Tao Shen.  (2023)  Gastrodin Ameliorates Knee Joint Inflammation and Pain in Osteoarthritis Rats and Prevents Chondrocyte Injury by Regulating PI3K/Akt/FoxO1 Pathway.  Pharmacognosy Magazine,      [PMID:] [10.1177/09731296231203860]

2. Baolin Huang, Zimin Lin, Zhenzhen Chen, Jiasheng Chen, Birui Shi, Jingjing Jia, Yuan Li, Yueqing Pan, Yuntao Liang, Zheng Cai.  (2023)  Strain differences in the drug transport capacity of intestinal glucose transporters in Sprague–Dawley versus Wistar rats, C57BL/6J versus Kunming mice.  INTERNATIONAL JOURNAL OF PHARMACEUTICS,      [PMID:37254285] [10.1016/j.ijpharm.2023.123000]

3. Sun Hao-Fei, Cui Yuan-Yuan, Li Hong-Liang, Yang Cheng-Xiong.  (2023)  Click postsynthesis of microporous organic network@silica composites for reversed-phase/hydrophilic interaction mixed-mode chromatography.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,  415  (18): (4533-4543).  [PMID:37017725] [10.1007/s00216-023-04680-0]

4. Qiang Yin, Ran Yan, Yan Wang, Jia Yu.  (2023)  Gastrodin from Gastrodia elata attenuates acute myocardial infarction by suppressing autophagy: Key role of the miR-30a-5p/ATG5 pathway.  Journal of Functional Foods,      [PMID:] [10.1016/j.jff.2023.105429]

5. Jin-Jin Song, Hui Li, Nan Wang, Xiao-Yan Zhou, Yan Liu, Zhen Zhang, Qian Feng, Yu-Ling Chen, Dan Liu, Jia Liang, Xiang-Yu Ma, Xiang-Ru Wen, Yan-Yan Fu.  (2022)  Gastrodin ameliorates the lipopolysaccharide-induced neuroinflammation in mice by downregulating miR-107-3p.  Frontiers in Pharmacology,      [PMID:36569291] [10.3389/fphar.2022.1044375]

6. Yuhong Wang, Kaixuan Luo, Junrui Li, Yehui Liao, Chengde Liao, Wen-Shiang Chen, Moxian Chen, Lijuan Ao.  (2022)  Focused Ultrasound Promotes the Delivery of Gastrodin and Enhances the Protective Effect on Dopaminergic Neurons in a Mouse Model of Parkinson’s Disease.  Frontiers in Cellular Neuroscience,      [PMID:35656407] [10.3389/fncel.2022.884788]

7. Yin Hua, Hu Tiandong, Zhuang Yibin, Liu Tao.  (2020)  Metabolic engineering of Saccharomyces cerevisiae for high-level production of gastrodin from glucose.  Microbial Cell Factories,  19  (1): (1-12).  [PMID:33243241] [10.1186/s12934-020-01476-0]

8. Limin Li, Bin Hao, Yulong Zhang, Shen Ji, Guixin Chou.  (2020)  Metabolite Profiling and Distribution of Militarine in Rats Using UPLC-Q-TOF-MS/MS.  MOLECULES,  25  (5): (1082).  [PMID:32121087] [10.3390/molecules25051082]

9. Lianfang Chen, Junjie Ou, Hongwei Wang, Zhongshan Liu, Mingliang Ye, Hanfa Zou.  (2016)  Tailor-Made Stable Zr(IV)-Based Metal–Organic Frameworks for Laser Desorption/Ionization Mass Spectrometry Analysis of Small Molecules and Simultaneous Enrichment of Phosphopeptides.  ACS Applied Materials & Interfaces,      [PMID:27427857] [10.1021/acsami.6b06225]

10. Yanfen Bai, Hua Yin, Huiping Bi, Yibin Zhuang, Tao Liu, Yanhe Ma.  (2016)  De novo biosynthesis of Gastrodin in Escherichia coli.  METABOLIC ENGINEERING,      [PMID:26804288] [10.1016/j.ymben.2016.01.002]

11. Qing Wang, Yao Long, Lin Yao, Li Xu, Zhi-Guo Shi, Lanying Xu.  (2015)  Preparation, characterization and application of a reversed phase liquid chromatography/hydrophilic interaction chromatography mixed-mode C18-DTT stationary phase.  TALANTA,      [PMID:26695288] [10.1016/j.talanta.2015.09.009]

12. Yanhong Bi, Ruiping Fu, Weiliang Hua, Xinyu Xiong, Chun Zhu, Xiaobao Nie, Zhaoyu Wang.  (2025)  An empirical exploration of the capacity of choline chloride/lactic acid eutectics to extract and stabilize natural polyhydroxy compounds.  FOOD CHEMISTRY,      [PMID:40120314] [10.1016/j.foodchem.2025.143873]

13. Chenran Xin, Pinhui Jia, Yan Zhao, Zhiqiang Cheng, Wencong Liu, Peng Di, Wei Li, Hongyan Zhu.  (2025)  Antioxidant effects of Gastrodia elata polysaccharide-based hydrogels loaded with puerarin/gelatin microspheres for D-galactose-induced aging-skin wound healing.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:39805458] [10.1016/j.ijbiomac.2025.139809]

14. Lin Ge, Yu Xia, Wenxin Xu, Ruobing Jia, Tingting Zhang.  (2025)  Efficient Biosynthesis of Gastrodin by UDP-Glycosyltransferase from Rauvolfia serpentina.  JOURNAL OF MICROBIOLOGY AND BIOTECHNOLOGY,      [PMID:40147927] [10.4014/jmb.2501.01002]

15. He Sun, Miao Li, Yunling Li, Na Zheng, Jiaxin Li, Xiang Li, Yingying Liu, Qianyun Ji, Liping Zhou, Jingwen Su, Wanxu Huang, Zhongbo Liu, Peng Liu, Libo Zou.  (2024)  Gastrodin Improves the Activity of the Ubiquitin–Proteasome System and the Autophagy–Lysosome Pathway to Degrade Mutant Huntingtin.  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  25  (14): (7709).  [PMID:39062952] [10.3390/ijms25147709]

16. Ge Xinyu, Wu Bozhao, Dou Xiaohui, Sun Mingchen, Wu Ji-ao, Sun Daqing.  (2025)  Gastrodin alleviates loperamide-induced slow transit constipation in mice by modulating the MAPK signaling pathway.  NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY,      [PMID:41134354] [10.1007/s00210-025-04763-y]

17. Ruijing Li, Weili Yang, Lijuan Zheng, Xingxue Yan, Cuihua Liu, Yaodong Zhang, Jitong Li.  (2025)  Gastrodin alleviates alcohol-induced developmental and neurotoxic effects in zebrafish larvae by suppressing ferroptosis via regulating the Nrf2/GPX4 signaling pathway.  TOXICOLOGY AND APPLIED PHARMACOLOGY,      [PMID:41371372] [10.1016/j.taap.2025.117684]

18. Hong Ding, Wen-Xuan Wang, Qiong-Dan Liang, Chuan-Feng Tang, Tang-Di Xu, Zi-An Miao, Bang-Xing Han, Ling-Dong Kong.  (2026)  Gastrodin alleviates high fructose-induced podocyte mitochondria-mediated apoptosis by inhibiting NLRP6 to facilitate TRIM7-triggered Bok mRNA degradation.  International Journal of Biological Sciences,  22  (3): (1162).  [PMID:41608624] [10.7150/ijbs.120307]

19. Haili Zhang, Ling Li, Zhihuang Zhao, Meidan Wang, Yangyan Ge, Shuqin Lu, Min Hu, Chenghong Xiao, Menglan Luo, Ting Lei, Liangyuan Li, Jinqiang Zhang.  (2026)  Systems pharmacology reveals the mechanism underlying gastrodiae rhizoma in improving stress-induced cognitive impairment: Protecting hippocampal synapses from excessive microglia-mediated pruning.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:] [10.1016/j.jep.2026.121482]