ChemicalBook Product Catalog Biochemical Engineering Chinese Herbs 10-Gingerol

10-Gingerol

Product Name10-Gingerol
CAS23513-15-7
MFC21H34O4
MW350.49
EINECS
MOL File23513-15-7.mol

Chemical Properties

Melting point	56-58 °C
Boiling point	499.7±35.0 °C(Predicted)
Density	1.037±0.06 g/cm3(Predicted)
Flash point	166℃
storage temp.	2-8°C
solubility	methanol: soluble5mg/mL, clear, colorless
form	Solid
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)

Safety Information

Risk Statements	53
Safety Statements	24/25
WGK Germany	3
HS Code	29145019
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Usage And Synthesis

Description

10-Gingerol is a phenol that has been found in Z. officinale and has diverse biological activities. It scavenges DPPH , 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; ) in isolated human polymorphonuclear (PMN) neutrophils when used at a concentration of 6 μM. 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. It is active against M. avium and M. tuberculosis (MICs = 25 and 50 μg/ml, respectively). 10-Gingerol (200 μM) is also cytotoxic to human MDA-MB-231 and MDA-MB-468 and murine 4T1 and EO771 mammary carcinoma cells.

Chemical Properties

White waxy, soluble in methanol, ethanol, DMSO and other organic solvents, 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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