| Identification | Back Directory | [Name]
10-Gingerol | [CAS]
23513-15-7 | [Synonyms]
10-GINGEROL
GINGEROL, 10-
10-Gingerol ,98%
(+)-(S)-[10]-Gingerol
10-GINGEROL, HPLC 98%
10-Gingerol USP/EP/BP
[10]-Gingerol Standard
10]-Gingerol >=95% (HPLC)
10-Gingerol, 98%, from Zingiber officinale Roscoe
5-hydroxy-1-(4-hydroxy-3-Methoxyphenyl)tetradecan-3-one
5-HYDROXY-1-(4-HYDROXY-3-METHOXYPHENYL)-3-TETRADECANONE
(S)-12-Oxo-14-(3-methoxy-4-hydroxyphenyl)tetradecane-10-ol
(S)-5-hydroxy-1-(4-hydroxy-3-Methoxyphenyl)tetradecan-3-one
(s)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-tetradecanone
(5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)tetradecan-3-one
(5S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-tetradecanone
(S)-1-(3-Methoxy-4-hydroxyphenyl)-5-hydroxytetradecane-3-one
(5S)-1-(3-Methoxy-4-hydroxyphenyl)-5-hydroxytetradecane-3-one
(5S)-5-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)tetradecan-3-one
3-Tetradecanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (5S)- | [Molecular Formula]
C21H34O4 | [MDL Number]
MFCD01682694 | [MOL File]
23513-15-7.mol | [Molecular Weight]
350.49 |
| Chemical Properties | Back Directory | [Melting point ]
56-58 °C | [Boiling point ]
499.7±35.0 °C(Predicted) | [density ]
1.037±0.06 g/cm3(Predicted) | [Fp ]
166℃ | [storage temp. ]
2-8°C | [solubility ]
methanol: soluble5mg/mL, clear, colorless | [form ]
neat | [pka]
10.02±0.20(Predicted) | [color ]
Yellow | [Water Solubility ]
practically insoluble in water | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [InChI]
InChI=1S/C21H34O4/c1-3-4-5-6-7-8-9-10-18(22)16-19(23)13-11-17-12-14-20(24)21(15-17)25-2/h12,14-15,18,22,24H,3-11,13,16H2,1-2H3/t18-/m0/s1 | [InChIKey]
AIULWNKTYPZYAN-SFHVURJKSA-N | [SMILES]
C(C1=CC=C(O)C(OC)=C1)CC(=O)C[C@@H](O)CCCCCCCCC | [LogP]
4.900 (est) |
| Hazard Information | Back Directory | [Description]
10-Gingerol is a phenol that has been found in Z. officinale and has diverse biological activities.1,2,3,4 It scavenges DPPH (Item No. 14805), superoxide, and hydroxyl radicals in cell-free assays (IC50s = 10.47, 1.68, and 1.35 μM, respectively) and inhibits oxidative burst induced by N-formyl-Met-Leu-Phe (fMLP; Item No. 21495) in isolated human polymorphonuclear (PMN) neutrophils when used at a concentration of 6 μM.1 10-Gingerol inhibits NETosis and the production of reactive oxygen species (ROS) induced by LPS or lupus-relevant stimuli, including ribonucleoprotein-containing immune complexes and anti-phospholipid antibodies, in isolated human neutrophils.2 It is active against M. avium and M. tuberculosis (MICs = 25 and 50 μg/ml, respectively).3 10-Gingerol (200 μM) is also cytotoxic to human MDA-MB-231 and MDA-MB-468 and murine 4T1 and EO771 mammary carcinoma cells.4 | [Chemical Properties]
It is white and waxy, soluble in organic solvents such as methanol, ethanol, and DMSO, and is derived from ginger. | [Uses]
(+)-(S)-[10]-Gingerol has been observed to exhibit anti-oxidant behaviour towards lipids and is effective in suppressing obesity and adipose tissue inflammation. | [Definition]
ChEBI: (10)-Gingerol is a beta-hydroxy ketone, a member of phenols and a monomethoxybenzene. | [Biochem/physiol Actions]
[10]-Gingerol is a bioactive compound found in ginger (Zingiber officinale) with anti-inflammatory and antioxidant activity. | [in vivo]
10-Gingerol (30 mg/kg, i.p., 7 consecutive days) reverses body weight loss, declines disease activity index (DAI), decreasing myeloperoxidase (MPO) activity and malondialdehyde (MDA) level, as well as restoring SOD activity, reduces the serum TNF-α and IL-1β levels, ameliorates mucosa inflammation and/or defect in rats with DSS-induced acute ulcerative colitis[4].
| Animal Model: | Rats with DSS-induced acute ulcerative colitis[4] | | Dosage: | 30 mg/kg | | Administration: | i.p., 7 consecutive days | | Result: | Reversed body weight loss and significantly declined DAI, reduced the serum TNF-α and IL-1β levels, ameliorated mucosa inflammation and/or defect in rats with DSS-induced acute ulcerative colitis in rats with DSS-induced acute ulcerative colitis. |
| [References]
[1] SWARNALATHA DUGASANI . Comparative antioxidant and anti-inflammatory effects of [6]-gingerol, [8]-gingerol, [10]-gingerol and [6]-shogaol[J]. Journal of ethnopharmacology, 2010, 127 2: Pages 515-520. DOI: 10.1016/j.jep.2009.10.004
[2] RAMADAN A ALI. Antineutrophil properties of natural gingerols in models of lupus.[J]. JCI insight, 2021. DOI: 10.1172/jci.insight.138385
[3] R. D. HISERODT R. T R S G Franzblau. Isolation of 6-, 8-, and 10-Gingerol from Ginger Rhizome by HPLC and Preliminary Evaluation of Inhibition of Mycobacterium avium and Mycobacterium tuberculosis[J]. Journal of Agricultural and Food Chemistry, 1998, 46 7: 2504-2508. DOI: 10.1021/jf970948l
[4] MEGAN M. BERNARD David W H Jason R McConnery. [10]-Gingerol, a major phenolic constituent of ginger root, induces cell cycle arrest and apoptosis in triple-negative breast cancer cells[J]. Experimental and molecular pathology, 2017, 102 2: Pages 370-376. DOI: 10.1016/j.yexmp.2017.03.006 |
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