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G1046

Sigma-Aldrich

[6]-Gingerol

≥98% (HPLC)

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Synonym(s):
3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (5S)-, 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone, 6-Gingerol
Empirical Formula (Hill Notation):
C17H26O4
CAS Number:
23513-14-6
Molecular Weight:
294.39
MDL number:
MFCD00210507
PubChem Substance ID:
329799719
NACRES:
NA.25

Quality Level

200

Assay

≥98% (HPLC)

storage condition

protect from light
under inert gas

solubility

methanol: 1 mg/mL, clear, colorless

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCCCC[C@H](O)CC(=O)CCc1ccc(O)c(OC)c1

InChI

1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3/t14-/m0/s1

InChI key

NLDDIKRKFXEWBK-AWEZNQCLSA-N

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General description

[6]-Gingerol is implicated in apoptosis, cell cycle regulation, cytotoxic activity and inhibition of angiogenesis. It prevents serotonin release and platelet aggregation. Gingerol has immunomodulatory, antiapoptotic, antihyperglycemic, antilipidemic and antiemetic properties.

Application

[6]-Gingerol has been used:
  • to study its effects on transient receptor potential (TRP) channels
  • to study its effects on experimental models of non-alcoholic steatohepatitis
  • to determine its effects on microsomal prostaglandine E2 synthase 1 (mPGES-1), glycogen synthase kinase 3β (GSK-3β) and β-catenin pathway in A549 cell line
  • to analyse the effects of 6-Shogaol (6-SG) on diabetic nephropathy (DN) in db/db mice

Biochem/physiol Actions

Bioactive compound found in ginger (Zingiber officinale) with antioxidant activity, which functions as an anti-inflammatory and antitumor agent. [6]-Gingerol down regulates proinflammatory cytokine release by macrophages. It has been shown to inhibit COX-2 expression by blocking the activation of p38 MAP kinase and NF-κB in phorbol ester-stimulated mouse skin.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Khairunnisa' Md Yusof et al.
Molecules (Basel, Switzerland), 20(6), 10280-10297 (2015-06-06)
Numerous bioactive compounds have cytotoxic properties towards cancer cells. However, most studies have used single compounds when bioactives may target different pathways and exert greater cytotoxic effects when used in combination. Therefore, the objective of this study was to determine
Khairunnisa' Md Yusof et al.
Journal of natural medicines (2019-06-10)
Our previous study reported that combined treatment of γ-tocotrienol with 6-gingerol showed promising anticancer effects by synergistically inhibiting proliferation of human colorectal cancer cell lines. This study aimed to identify and elucidate molecular mechanisms involved in the suppression of SW837
Revealing the effect of 6-gingerol, 6-shogaol and curcumin on mPGES-1, GSK-3beta and beta-catenin pathway in A549 cell line
Eren D and Betul YM
Chemico-Biological Interactions, 258, 257-265 (2016)
Effect of Herbal Supplement-Drug Interactions on Therapeutic Drug Monitoring
Chin AC and Baskin LB
Therapeutic Drug Monitoring, 417-445 (2012)
[6]-Gingerol dampens hepatic steatosis and inflammation in experimental nonalcoholic steatohepatitis
Tzeng TF, et al.
Phytomedicine, 22(4), 452-461 (2015)
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NF-κB and Inflammation

Chronic inflammation is an underlying factor in the development and progression of many of the chronic diseases of aging, such as arthritis, atherosclerosis, diabetes, and cancer.

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