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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:
Molecular Weight:
294.39
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

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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This Item
SMB00311PHL89201345868
vibrant-m

G1046

[6]-Gingerol

vibrant-m

SMB00311

Shogaol

vibrant-m

PHL89201

6-Gingerol

vibrant-m

345868

[6]-Gingerol, Zingiber officinale

assay

≥98% (HPLC)

assay

≥90% (HPLC)

assay

≥90.0% (HPLC)

assay

≥95% (HPLC)

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

100

solubility

methanol: 1 mg/mL, clear, colorless

solubility

-

solubility

-

solubility

DMSO: 5 mg/mL

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

storage condition

protect from light

storage condition

-

storage condition

-

storage condition

OK to freeze, protect from light

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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[6]-Gingerol dampens hepatic steatosis and inflammation in experimental nonalcoholic steatohepatitis
Tzeng TF, et al.
Phytomedicine, 22(4), 452-461 (2015)
Yun Xu et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 97, 633-641 (2017-11-05)
The prevalence of type 2 diabetes mellitus has been increasing worldwide and more than two thirds of the patients may develop diabetic nephropathy (DN). However, the efficiency of existing approaches on DN progression is limited. 6-Shogaol (6-SG), a major dehydrated
Biological properties of 6-gingerol: a brief review.
Wang S, et al.
Natural Product Communications, 9(7), 1027-1030 (2014)
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
Effect of Herbal Supplement-Drug Interactions on Therapeutic Drug Monitoring
Chin AC and Baskin LB
Therapeutic Drug Monitoring, 417-445 (2012)

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