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| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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Basic Description
| 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 | |
|---|---|
| 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. |
Associated Targets(Human)
TRPV1 Tclin Transient receptor potential cation channel subfamily V member 1 (2 Activities)
HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
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ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)
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ACHE Tclin Acetylcholinesterase (18204 Activities)
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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)
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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
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LTA4H Tchem Leukotriene A4 hydrolase (1442 Activities)
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CYP2C8 Tchem Cytochrome P450 2C8 (1492 Activities)
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TRPV1 Tclin Vanilloid receptor (8273 Activities)
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BCHE Tclin Butyrylcholinesterase (7174 Activities)
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APP Tclin Amyloid-beta A4 protein (8510 Activities)
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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
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CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
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CYP2E1 Tchem Cytochrome P450 2E1 (2174 Activities)
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CYP2A6 Tchem Cytochrome P450 2A6 (2861 Activities)
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CYP2B6 Tchem Cytochrome P450 2B6 (1338 Activities)
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HT-29 (80576 Activities)
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IMR-32 (1082 Activities)
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NCI-H1299 (3248 Activities)
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HCT-116 (91556 Activities)
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HepG2 (196354 Activities)
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NLRP3 Tchem NACHT, LRR and PYD domains-containing protein 3 (908 Activities)
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SNU-182 (48 Activities)
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Associated Targets(non-human)
Abcb1b P-glycoprotein 1 (174 Activities)
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Rodentolepis nana (555 Activities)
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PC-12 (7051 Activities)
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RBL-2H3 (1162 Activities)
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C6 (2371 Activities)
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BV-2 (3710 Activities)
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Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)
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Plasma (328 Activities)
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Mapt Microtubule-associated protein tau (6 Activities)
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Names and Identifiers
| IUPAC Name | (E)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one |
|---|---|
| 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 |
Certificates
Certificate of Analysis(COA)
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Safety and Hazards(GHS)
| Pictogram(s) | GHS07 |
|---|---|
| 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 |
Related Documents
Citations of This Product
| 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] |
References
| 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] |
| 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] |