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Synonyms | [6]-Shogaol;6-Shogaol | 6-Shogaol | AC-34334 | NSC752389 | NSC-752389 | Q2746448 | (E)-1-(4-Hydroxy-3- methoxyphenyl)dec-4-en-3-one | [(E)-1-(4-hydroxy-3-methoxyphenyl)-dec-4-en-3-one] | 1-(4-Hydroxy-3-methoxyphenyl)-4-dodecen-3-one, 9CI | BDBM50237536 | |
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Specifications & Purity | Moligand™, ≥90%(HPLC) |
Storage Temp | Store at 2-8°C |
Shipped In | Wet ice |
Grade | Moligand™ |
Product Description | Description Shogaol or 6-shogaol, the pungent metabolite of dried ginger, is one of the main bioactive compounds extracted from the natural dietary rhizome,Zingiber officinaleRoscoe (ginger). It is the dehydrated successor of 6-gingerol with an α,β-unsaturated ketone skeleton.Shogaol has been used to determine its safe dose to evaluate potential toxicity in higher concentrations in mice models. It has also been used to investigate its antioxidant effects on the modulation of TRPC5 (ITRPC5) and TRPA1 (ITRPA1) currents. |
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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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IUPAC Name | (E)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one |
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INCHI | InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+ |
InChi Key | OQWKEEOHDMUXEO-BQYQJAHWSA-N |
Canonical SMILES | CCCCCC=CC(=O)CCC1=CC(=C(C=C1)O)OC |
Isomeric SMILES | CCCCC/C=C/C(=O)CCC1=CC(=C(C=C1)O)OC |
WGK Germany | 3 |
Alternate CAS | 23513-13-5,555-66-8 |
PubChem CID | 5281794 |
NSC Number | 752389 |
MeSH Entry Terms | (6)-shogaol;6-shogaol;shogaol |
Molecular Weight | 276.37 |
Beilstein | 2056098 |
Enter Lot Number to search for COA:
Pictogram(s) | GHS07 |
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Signal | Warning |
Hazard Statements | H302:Harmful if swallowed |
Precautionary Statements | P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P270:Do not eat, drink or smoke when using this product. P330:Rinse mouth. P301+P317:IF SWALLOWED: Get medical help. |
WGK Germany | 3 |
1. 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] |
2. Rui Bao, Qi-Long Wang, Ran Li, Michael Adu-Frimpong, Elmurat Toreniyazov, Hao Ji, Xi-Ming Xu, Jiang-Nan Yu. (2020) Improved oral bioavailability and target delivery of 6-shogaol via vitamin E TPGS-modified liposomes: Preparation, in-vitro and in-vivo characterizations. JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY, 59 (101842). [PMID:] [10.1016/j.jddst.2020.101842] |
3. Huiyun Zhang, Qilong Wang, Congyong Sun, Yuan Zhu, Qiuxuan Yang, Qiuyu Wei, Jiaxin Chen, Wenwen Deng, Michael Adu-Frimpong, Jiangnan Yu, Ximing Xu. (2019) Enhanced Oral Bioavailability, Anti-Tumor Activity and Hepatoprotective Effect of 6-Shogaol Loaded in a Type of Novel Micelles of Polyethylene Glycol and Linoleic Acid Conjugate. Pharmaceutics, 11 (3): (107). [PMID:30845761] [10.3390/pharmaceutics11030107] |
1. Han Q, Yuan Q, Meng X, Huo J, Bao Y, Xie G. (2017) 6-Shogaol attenuates LPS-induced inflammation in BV2 microglia cells by activating PPAR-γ.. Oncotarget, 8 (26): (42001-42006). [PMID:28410218] [10.1021/op500134e] |
2. Young-Soo Kim,Chan Sik Hong,Sang Weon Lee,Joo Hyun Nam,Byung Joo Kim. (2016-11-15) Effects of ginger and its pungent constituents on transient receptor potential channels.. International journal of molecular medicine, 38 ((6)): (1905-1914). [PMID:27840893] |
3. Xingran Kou,Xiaoqi Wang,Ruya Ji,Lang Liu,Yening Qiao,Zaixiang Lou,Chaoyang Ma,Shiming Li,Hongxin Wang,Chi-Tang Ho. (2018-02-09) Occurrence, biological activity and metabolism of 6-shogaol.. Food & function, 9 ((3)): (1310-1327). [PMID:29417118] |
4. Jin-Hyung Lee,Yong-Guy Kim,Pilju Choi,Jungyeob Ham,Jae Gyu Park,Jintae Lee. (2018-09-14) Antibiofilm and Antivirulence Activities of 6-Gingerol and 6-Shogaol Against Candida albicans Due to Hyphal Inhibition.. Frontiers in cellular and infection microbiology, 8 (299-299). [PMID:30211127] |
5. H-R Kim,Y-B Eom. (2020-09-28) Antifungal and anti-biofilm effects of 6-shogaol against Candida auris.. Journal of applied microbiology, 130 ((4)): (1142-1153). [PMID:32981148] |
6. Ali Ghasemzadeh,Hawa Z E Jaafar,Ali Baghdadi,Amin Tayebi-Meigooni. (2018-07-07) Formation of 6-, 8- and 10-Shogaol in Ginger through Application of Different Drying Methods: Altered Antioxidant and Antimicrobial Activity.. Molecules (Basel, Switzerland), 23 ((7)): [PMID:29976903] |
7. Lingli Yang,Fei Yang,Lanting Teng,Ichiro Katayama. (2020-05-21) 6-Shogaol Protects Human Melanocytes against Oxidative Stress through Activation of the Nrf2-Antioxidant Response Element Signaling Pathway.. International journal of molecular sciences, 21 ((10)): [PMID:32429495] |
8. 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] |
9. Rui Bao, Qi-Long Wang, Ran Li, Michael Adu-Frimpong, Elmurat Toreniyazov, Hao Ji, Xi-Ming Xu, Jiang-Nan Yu. (2020) Improved oral bioavailability and target delivery of 6-shogaol via vitamin E TPGS-modified liposomes: Preparation, in-vitro and in-vivo characterizations. JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY, 59 (101842). [PMID:] [10.1016/j.jddst.2020.101842] |
10. Huiyun Zhang, Qilong Wang, Congyong Sun, Yuan Zhu, Qiuxuan Yang, Qiuyu Wei, Jiaxin Chen, Wenwen Deng, Michael Adu-Frimpong, Jiangnan Yu, Ximing Xu. (2019) Enhanced Oral Bioavailability, Anti-Tumor Activity and Hepatoprotective Effect of 6-Shogaol Loaded in a Type of Novel Micelles of Polyethylene Glycol and Linoleic Acid Conjugate. Pharmaceutics, 11 (3): (107). [PMID:30845761] [10.3390/pharmaceutics11030107] |