Determine the necessary mass, volume, or concentration for preparing a solution.
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| SKU | Size | Availability |
Price | Qty |
|---|---|---|---|---|
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G109797-1g
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1g |
4
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$21.90
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G109797-5g
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5g |
4
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$98.90
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G109797-25g
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25g |
4
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$159.90
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G109797-100g
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100g |
3
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$574.90
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Gap junction inhibitor
| Synonyms | 18 beta -Glycyrrhetinic Acid | 3-beta-Hydroxy-11-oxoolean-12-en-30-oic acid | 3beta-Hydroxy-11-oxoolean-12-en-30-oic acid | ENOXOLONE [MI] | DTXCID50669 | Enoxolone (Glycyrrhetin) | (5S,8S,15S,18S,1R,2R,10R,14R,20R)-18-hydroxy-1,2,5,8,15,19,19-heptamethyl |
|---|---|
| Specifications & Purity | Moligand™, ≥97% |
| Biochemical and Physiological Mechanisms | Gap junction inhibitor. Antiviral activity against rotavirus replication in vitro . Shows immunomodulatory, chemopreventive and anti-inflammatory effects in vivo. Orally active. |
| Shipped In | Normal |
| Grade | Moligand™ |
| Action Type | INHIBITOR |
| Mechanism of action | Inhibitor of hydroxysteroid 11-beta dehydrogenase 1;Inhibitor of hydroxysteroid 11-beta dehydrogenase 2 |
| Note | 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. |
| Product Description |
18 β-Glycyrrhetinic Acid is an aglycone of the triterpenoid Glyccyrrhizic acid, which is found in liquorice. inhibits the PGDH (15-hydroxyprostaglandin dehydrogenase) leading to increased prostaglandin concentration in the digestive system. Also investigated for potential antibiotic activities. |
Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Triterpenoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Triterpenoids |
| Alternative Parents | Cyclohexenones Secondary alcohols Cyclic alcohols and derivatives Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aliphatic homopolycyclic compounds |
| Substituents | Triterpenoid - Cyclohexenone - Cyclic alcohol - Secondary alcohol - Ketone - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. |
| External Descriptors | Oleanane triterpenoids |
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| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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| Pubchem Sid | 488181083 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/488181083 |
| IUPAC Name | (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid |
| INCHI | InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1 |
| InChIKey | MPDGHEJMBKOTSU-YKLVYJNSSA-N |
| Smiles | CC1(C2CCC3(C(C2(CCC1O)C)C(=O)C=C4C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C |
| Isomeric SMILES | C[C@]12CC[C@](C[C@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)(C)C(=O)O |
| WGK Germany | 3 |
| RTECS | RK0180000 |
| Molecular Weight | 470.68 |
| Beilstein | 2229654 |
| Reaxy-Rn | 3041142 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3041142&ln= |
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
| Certificate of Analysis | Dec 06, 2023 | G109797 | |
| Certificate of Analysis | Dec 06, 2023 | G109797 | |
| Certificate of Analysis | Dec 06, 2023 | G109797 | |
| Certificate of Analysis | May 06, 2023 | G109797 | |
| Certificate of Analysis | Nov 23, 2022 | G109797 | |
| Certificate of Analysis | Nov 23, 2022 | G109797 | |
| Certificate of Analysis | Nov 23, 2022 | G109797 | |
| Certificate of Analysis | Nov 23, 2022 | G109797 | |
| Certificate of Analysis | Nov 23, 2022 | G109797 | |
| Certificate of Analysis | Nov 23, 2022 | G109797 | |
| Certificate of Analysis | Nov 23, 2022 | G109797 | |
| Certificate of Analysis | Nov 23, 2022 | G109797 | |
| Certificate of Analysis | Nov 23, 2022 | G109797 | |
| Certificate of Analysis | Feb 14, 2022 | G109797 | |
| Certificate of Analysis | Feb 14, 2022 | G109797 | |
| Certificate of Analysis | Feb 14, 2022 | G109797 | |
| Certificate of Analysis | Feb 14, 2022 | G109797 |
| Specific Rotation[α] | 162 ° (C=1, MeOH) |
|---|---|
| Melt Point(°C) | 292-295°C |
| Molecular Weight | 470.700 g/mol |
| XLogP3 | 6.400 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Exact Mass | 470.34 Da |
| Monoisotopic Mass | 470.34 Da |
| Topological Polar Surface Area | 74.600 Ų |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Complexity | 965.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 9 |
| 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 |
| 1. Yang Y, Zhu Q, Zhong Y, Cui X, Jiang Z, Wu P, Zheng X, Zhang K, Zhao S. (2020) Synthesis, anti-microbial and anti-inflammatory activities of 18β-glycyrrhetinic acid derivatives.. Bioorg Chem, 101 (103985). |
| 2. Omar Mezghrani,Yue Tang,Xue Ke,Yi Chen,Danrong Hu,Jiasheng Tu,Li Zhao,Nadia Bourkaib. (2014-12-03) Hepatocellular carcinoma dually-targeted nanoparticles for reduction triggered intracellular delivery of doxorubicin.. International journal of pharmaceutics, 478 ((2)): (553-568). |
| 3. Linjun Zou, Yong Hou, Jiawen Zhang, Meiying Chen, Peiying Wu, Changcun Feng, Qinglong Li, Xudong Xu, Zhaocui Sun, Guoxu Ma. (2023) Degradable carrier-free spray hydrogel based on self-assembly of natural small molecule for prevention of postoperative adhesion. Materials Today Bio, 22 (100755). |
| 4. Qing Yao, Yingying Tang, Sheng Dai, Lihui Huang, Zewei Jiang, Shiming Zheng, Meng Sun, Yitianhe Xu, Ruijie Lu, Tuyue Sun, Huirong Huang, Xinyu Jiang, Xiaomin Yao, Guangyong Lin, Longfa Kou, Ruijie Chen. (2023) A Biomimetic Nanoparticle Exerting Protection against Acute Liver Failure by Suppressing CYP2E1 Activity and Scavenging Excessive ROS. Advanced Healthcare Materials, (2300571). |
| 5. Liu Cui, Xi Wang, Zhaoyun Liu, Ziqi Li, Ziwei Bai, Kui Lin, Jian Yang, Yuanlu Cui, Fei Tian. (2023) Metal-organic framework decorated with glycyrrhetinic acid conjugated chitosan as a pH-responsive nanocarrier for targeted drug delivery. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 240 (124370). |
| 6. Wen Zhijie, Fu Hudie, Ye Xuexin, Yang Xuedan, Zhu Shengpeng, Hu Jie, Kang Li, Li Xiaojun, Yang Xinzhou, Hu Yan. (2023) Antitumor activities of novel glycyrrhetinic acid-modified lipogel hybrid system in vitro. JOURNAL OF MATERIALS SCIENCE, 58 (13): (5788-5807). |
| 7. Jie Hu, Yongsheng Zheng, Zhijie Wen, Hudie Fu, Xuedan Yang, Xuexin Ye, Shengpeng Zhu, Li Kang, Xiaojun Li, Xinzhou Yang, Yan Hu. (2023) Construction of redox-sensitive liposomes modified by glycyrrhetinic acid and evaluation of anti-hepatocellular carcinoma activity. CHEMISTRY AND PHYSICS OF LIPIDS, 252 (105292). |
| 8. Fanli Shi, Ruilong Li, Wenjing Wang, Xiangyu Yu, Fenxia Zhu, Yiping Huang, Jing Wang, Zhenhai Zhang. (2023) Carboxymethyl starch as a solid dispersion carrier to enhance the dissolution and bioavailability of piperine and 18β-glycyrrhetinic acid. DRUG DEVELOPMENT AND INDUSTRIAL PHARMACY, |
| 9. Yanmin Shen, Ruoyu Li, Peixia Zhao, Wenju Liu, Xiaolong Yang, Zheng Zhang. (2022) Equilibrium Solubility of 18β-Glycyrrhetinic Acid in 12 Pure Solvents: Determination, Correlation, and Hansen Solubility Parameter. JOURNAL OF CHEMICAL AND ENGINEERING DATA, 67 (10): (3243–3251). |
| 10. Li Li, Anqi Chen, Bingmi Liu, Hao Pan, Yanjie Yu, Yu Liu. (2022) Preparation and pharmacokinetics of glycyrrhetinic acid and cell transmembrane peptides modified with liposomes for liver targeted-delivery. Biomedical Materials, 17 (4): (45006). |
| 11. Lulu Jin, Zhixin Zhu, Liangjie Hong, Zhefeng Qian, Fang Wang, Zhengwei Mao. (2023) ROS-responsive 18β-glycyrrhetic acid-conjugated polymeric nanoparticles mediate neuroprotection in ischemic stroke through HMGB1 inhibition and microglia polarization regulation. Bioactive Materials, 19 (38). |
| 12. Di Zhang, Jianxin Sun, Shiquan Chang, Xing Li, Huimei Shi, Bei Jing, Yachun Zheng, Yi Lin, Guoqiang Qian, Yuwei Pan, Guoping Zhao. (2021) Protective effect of 18β‑glycyrrhetinic acid against H2O2‑induced injury in Schwann cells based on network pharmacology and experimental validation. Experimental and Therapeutic Medicine, 22 (5): (1-9). |
| 13. Feng Yunhui, Mei Liyan, Wang Maojie, Huang Qingchun, Huang Runyue. (2021) Anti-inflammatory and Pro-apoptotic Effects of 18beta-Glycyrrhetinic Acid In Vitro and In Vivo Models of Rheumatoid Arthritis. Frontiers in Pharmacology, 12 (1688). |
| 14. Hao Liu, Sijiao Wang, Houyin Shi, Ruirui Zhang, Kunyan Qu, Yue Hu, Xingyu Qu, Chenyun Gan, Jingjing Chen, Xinyu Shi, Mengwu Zhang, Weiling Zeng. (2021) Gastric floating tablet improves the bioavailability and reduces the hypokalemia effect of gossypol in vivo. SAUDI PHARMACEUTICAL JOURNAL, 29 (305). |
| 15. Ruoning Wang, Xin Wang, Xiaoshun Jia, Honglan Wang, Wen Li, Junsong Li. (2020) Impacts of particle size on the cytotoxicity, cellular internalization, pharmacokinetics and biodistribution of betulinic acid nanosuspensions in combined chemotherapy. INTERNATIONAL JOURNAL OF PHARMACEUTICS, 588 (119799). |
| 16. Li Li, Shasha Han, Chun Yang, Lin Liu, Sengqun Zhao, Xiaofang Wang, Bingmi Liu, Hao Pan, Yu Liu. (2020) Glycyrrhetinic acid modified MOFs for the treatment of liver cancer. NANOTECHNOLOGY, 31 (32): (325602). |
| 17. Kaili Wang, Chunjing Guo, Shaohua Zou, Yueming Yu, Xinxin Fan, Bingjie Wang, Mengna Liu, Lei Fang, Daquan Chen. (2018) Synthesis, characterization and in vitro/in vivo evaluation of novel reduction-sensitive hybrid nano-echinus-like nanomedicine. Artificial Cells Nanomedicine and Biotechnology, |
| 18. Saisai Wang, Yong Shen, Runfeng Qiu, Zhiliang Chen, Zhehang Chen, Wenbin Chen. (2017) 18 β-glycyrrhetinic acid exhibits potent antitumor effects against colorectal cancer via inhibition of cell proliferation and migration. INTERNATIONAL JOURNAL OF ONCOLOGY, 51 (2): (615-624). |
| 19. Ping Zhang, Yang Cao, Huali Chen, Bo Zhou, Wenjing Hu, Liangke Zhang. (2017) Preparation and evaluation of glycyrrhetinic acid-modified and honokiol-loaded acoustic nanodroplets for targeted tumor imaging and therapy with low-boiling-point phase-change perfluorocarbon. Journal of Materials Chemistry B, 5 (29): (5845-5853). |
| 20. Dagen Zhong, Zonghua Liu, Shasha Xie, Wei Zhang, Yuanming Zhang, Wei Xue. (2012) Study on poly(D,L-lactic) microspheres embedded in calcium alginate hydrogel beads as dual drug delivery systems. JOURNAL OF APPLIED POLYMER SCIENCE, 129 (2): (767-772). |
| 21. Ma Xuan, Sun Zhenou, Chen Hui, Cao Lixing, Zhao Shuang, Fan Lihong, Zhao Chong, Yin Shutao, Hu Hongbo. (2024) 18β-glycyrrhetinic acid suppresses Lewis lung cancer growth through protecting immune cells from ferroptosis. CANCER CHEMOTHERAPY AND PHARMACOLOGY, (1-11). |
| 22. Qianhui Zhao, Xinhang Li, Jun Wen, Yinhui He, Nenggan Zheng, Wenchang Li, Albert Cardona, Zhefeng Gong. (2024) A two-layer neural circuit controls fast forward locomotion in Drosophila. CURRENT BIOLOGY, |