[6]-Gingerol - Moligand™, analytical standard, ≥98% , Activator of TRPA1, CAS No.23513-14-6, Activator of TRPA1

CAS: 23513-14-6 Cat. No.: G111261 Peso molecular: 294.39 Número EC: 607-241-6

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

Synonyms

3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)-(+)- | HMS1361D09 | (+)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone | CCG-208214 | HY-14615 | [1-(4''-hydroxy-3''-methoxyphenyl)-5-hydroxy-3-decanone] | 925QK2Z900 | AKOS006222484

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Descripción general

Gingerol, a phenolic substance and a potent cardiotonic agent isolated from the rhizome of ginger, has been shown to stimulate the Ca2+-pumping activity of sarcoplasmic reticulum (SR) of rabbits in a concentration-dependent manner. It was noted that Gingerol specifically activated SERCA (Ca2+-ATPase of cardiac and skeletal SR). Additional research has shown Gingerol to inhibit platelet aggregation via suppression of thromboxane production. Gingerol blocked ATP release from platelets induced by adrenaline and adenosine 5-diphosphate and prevented secondary aggregation. It has been demonstrated that Gingerol contains antioxidant and antiinflammatory characteristics and could significantly inhibit 7,12-dimethylbenz[a]anthracene-induced skin papillomagenesis in mice. Furthermore, Gingerol has been noted as an agonist of the capsaicin-activated VR1 (vanilloid receptor) and in leukemia cell studies it has been shown to have apoptotic properties.

Specifications

Sinónimos

3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)-(+)- | HMS1361D09 | (+)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone | CCG-208214 | HY-14615 | [1-(4''-hydroxy-3''-methoxyphenyl)-5-hydroxy-3-decanone] | 925QK2Z900 | AKOS006222484

Especificaciones y pureza

Moligand™, analytical standard, ≥98%

Mecanismos bioquímicos y fisiológicos

A bioactive compound with antioxidant activity found in ginger, which can be used as an anti-inflammatory and anti-tumor agent. 6-gingerol downregulates the release of pro-inflammatory cytokines through macrophages. It has been proven that it can block p3

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -20°C, Argon charged

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Analytical standard, Moligand™

Tipo de acción

ACTIVATOR

Mecanismo de acción

Activator of TRPA1

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%

Nombres e identificadores

• Sonrisas canónicas: CCCCCC(CC(=O)CCC1=CC(=C(C=C1)O)OC)O
• IUPAC Name: (5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
• InChIKey: NLDDIKRKFXEWBK-AWEZNQCLSA-N
• INCHI: 1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3/t14-/m0/s1
• Isómeros SMILES: CCCCC[C@@H](CC(=O)CCC1=CC(=C(C=C1)O)OC)O
• WGK Alemania: 3
• RTECS: HE0757000
• Número ONU: 2811
• Peso molecular: 294.39
• Reaxy-Rn: 2059333
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2059333&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Clase Phenols
      • Subclass Methoxyphenols

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Phenols
• Subclass: Methoxyphenols
• Intermediate Tree Nodes: Not available
• Direct Parent: Gingerols
• Alternative Parents: Fatty alcohols Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Beta-hydroxy ketones Secondary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Gingerol - Fatty alcohol - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Monocyclic benzene moiety - Beta-hydroxy ketone - Fatty acyl - Ketone - Secondary alcohol - Ether - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organic oxygen compound - Alcohol - Organooxygen compound - Aromatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as gingerols. These are compounds containing a gingerol moiety, which is structurally characterized by a 4-hydroxy-3-methoxyphenyl group substituted at the C6 carbon atom by a 5-hydroxy-alkane-3-one.
• External Descriptors: Zingiber derived compounds

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

Objetivos asociados (humanos)

TRPA1 Tclin Transient receptor potential cation channel subfamily A member 1 (0 Activities)

Discover Target: TRPA1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Propiedades químicas y físicas

• Solubilidad: Soluble in ethanol, benzene, ether, chloroform, methanol (1 mg/ml), and DMSO. Insoluble in water.
• Sensibilidad: Light ＆ heat sensitive.
• Peso molecular: 294.400 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 294.183 Da
• Monoisotopic Mass: 294.183 Da
• Topological Polar Surface Area: 66.800 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 293.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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

Referencias

1. Zhang Sheng-Feng, Li Jing, Wei Mei-Jie, Kong Fen-Ying, Zhang Rui, Wang Zhong-Xia, Fang Hai-Lin, Wang Wei.  (2023)  Highly sensitive electrochemical sensing of 6-gingerol in ginger using AuNPs-ZnO-rGO nanocomposites modified electrode.  IONICS,  29  (4): (1571-1578).  [PMID:] [10.1007/s11581-023-04890-7]

2. Xiaomin Zhang, Gaofeng Hu, Chaoyang Xu, Wen Nie, Kezhou Cai, Hongmei Fang, Baocai Xu.  (2023)  Inhibition of benzo[a]pyrene formation in charcoal-grilled pork sausages by ginger and its key compounds.  JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE,  103  (6): (2838-2847).  [PMID:36700254] [10.1002/jsfa.12470]

3. Zhang Changrong, Huang Yongquan, Li Peiwu, Chen Xinlin, Liu Fengbin, Hou Qiuke.  (2020)  Ginger relieves intestinal hypersensitivity of diarrhea predominant irritable bowel syndrome by inhibiting proinflammatory reaction.  BMC Complementary Medicine and Therapies,  20  (1): (1-10).  [PMID:32928188] [10.1186/s12906-020-03059-3]

4. Ying Liu, ShiJi Deng, Zhi Zhang, Yue Gu, ShengNan Xia, XinYu Bao, Xiang Cao, Yun Xu.  (2020)  6-Gingerol attenuates microglia-mediated neuroinflammation and ischemic brain injuries through Akt-mTOR-STAT3 signaling pathway.  EUROPEAN JOURNAL OF PHARMACOLOGY,      [PMID:32681941] [10.1016/j.ejphar.2020.173294]

5. Lijun Zhen, Qiuyu Wei, Qilong Wang, Huiyun Zhang, Michael Adu-Frimpong, Caleb Kesse Firempong, Ximing Xu, Jiangnan Yu.  (2020)  Preparation and in vitro/in vivo evaluation of 6-Gingerol TPGS/PEG-PCL polymeric micelles.  PHARMACEUTICAL DEVELOPMENT AND TECHNOLOGY,      [PMID:30557068] [10.1080/10837450.2018.1558239]

6. Min Zhang, Ying Peng, Mengyue Wang, Beibei Gao, Lijuan Zhao, Xiaobo Li.  (2018)  The influence of compatibility of Si-Ni decoction with metabolism in intestinal bacteria on transports of toxic diterpenoid alkaloids from processed aconite root across Caco-2 monolayers.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:30223050] [10.1016/j.jep.2018.09.022]

7. Qilong Wang, Qiuyu Wei, Qiuxuan Yang, Xia Cao, Qiang Li, Feng Shi, Shan Shan Tong, Chunlai Feng, Qingtong Yu, Jiangnan Yu, Ximing Xu.  (2017)  A novel formulation of [6]-gingerol: Proliposomes with enhanced oral bioavailability and antitumor effect.  INTERNATIONAL JOURNAL OF PHARMACEUTICS,      [PMID:29126908] [10.1016/j.ijpharm.2017.11.006]

8. Yang Xu, Qilong Wang, Yingshu Feng, Caleb Kesse Firempong, Yuan Zhu, Emmanuel Omari-Siaw, Yuanyuan Zheng, Zunqin Pu, Ximing Xu, Jiangnan Yu.  (2016)  Enhanced oral bioavailability of [6]-Gingerol-SMEDDS: Preparation, in vitro and in vivo evaluation.  Journal of Functional Foods,      [PMID:] [10.1016/j.jff.2016.10.007]

9. Zhenhao Li, Shun Xiao, Ni Ai, Kedi Luo, Xiaohui Fan, Yiyu Cheng.  (2014)  Derivative multiple reaction monitoring and single herb calibration approach for multiple components quantification of traditional Chinese medicine analogous formulae.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:25541090] [10.1016/j.chroma.2014.12.024]

10. Yanni Tai, Mintong Zhao, Feng Ding, Gelin Wu, Haibin Qu, Ping Gong, Yongjian Xie, Peng Zhou, Xingchu Gong.  (2024)  Analytical quality by design based on knowledge organization: A case study of developing an ultrahigh-performance liquid chromatography method for the detection of phenolic compounds.  PHYTOCHEMICAL ANALYSIS,      [PMID:38462508] [10.1002/pca.3343]

11. Rui Wang, Pei-Feng Guo, Jing Nie, Xing Hu, Yu-Wei Wu, Shu Zhu, Bo-Ru Chen, Jian Li, Xin-An Zeng, Fei-Yue Xu.  (2024)  Inhibitory mechanism of xanthine oxidase by 6-, 8- and 10-gingerol: Enzyme kinetics, multi-spectroscopy and molecular simulations.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2024.125605]

12. Jiehong He, Tian Wang, Yuanyuan Xie, Xianrui Liang.  (2024)  Preparation and characterization of self-assembling nanoparticles in Gancao Ganjiang decoction.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2024.125174]

13. Zhen Liu, Ning Xu, Jumei Hou, Tong Liu.  (2024)  TbNACα negatively regulates Trichoderma breve T069 synthesis of ethyl caffeate and enhances antagonism of Sclerotium rolfsii1.  Journal of Integrative Agriculture,      [PMID:] [10.1016/j.jia.2024.01.030]

14. Yang Zhang, Siyi Yang, Wensi Li, Xiaoyan Li, Xiangqin Lai, Xiang Li, Wuwan Xiong, Bo Zhang.  (2025)  Optimized High-Pressure Ultrasonic-Microwave-Assisted Extraction of Gingerol from Ginger: Process Design and Performance Evaluation.  Processes,  13  (7): (2149).  [PMID:] [10.3390/pr13072149]

15. Yanyan Nong, Hui Li, Yueen Ou, Luanyu Xie, Caimin Fen, Hong Gao, Guidong Huang, Zhiming Zhang, Senwei Hu.  (2025)  Effects of lactic acid bacteria on sensory evaluation and flavor compounds of fermented baby ginger jam.  Applied Food Research,      [PMID:] [10.1016/j.afres.2025.101426]

16. Jiajia Wang, Hongru He, Lianbing Lin, Yicen Lin, Feng Wang.  (2025)  Quality attributes, metabolomics and microbial community dynamics of naturally fermented Xiaohuang ginger (Zingiber officinale cv. Xiaohuang): A ready-to-eat flavoring food.  Food Chemistry-X,      [PMID:41323687] [10.1016/j.fochx.2025.103237]

17. Zongmei Huang, Cong-Ting Wu, Jing Li, Lu-Shuang Li.  (2026)  One-step synthesis of dual-emission carbon dots for ratiometric fluorescence sensing of curcumin in food samples.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2026.116897]

18. Mintong Zhao, Zhilong Tang, Mingyang Zhou, Xiaohan Zhang, Xinyu Wang, Xingchu Gong.  (2026)  Online monitoring of Chinese herbal medicine production process toward lean six sigma: multimodal data fusion based on transformer architecture.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:41610806] [10.1016/j.saa.2026.127507]