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G1046

Sigma-Aldrich

[6]-Gingerol

≥98% (HPLC)

Sinônimo(s):

3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (5S)-, 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone, 6-Gingerol

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About This Item

Fórmula empírica (Notação de Hill):
C17H26O4
Número CAS:
Peso molecular:
294.39
Número MDL:
Código UNSPSC:
12352205
ID de substância PubChem:
NACRES:
NA.25

Nível de qualidade

Ensaio

≥98% (HPLC)

condição de armazenamento

protect from light
under inert gas

solubilidade

methanol: 1 mg/mL, clear, colorless

aplicação(ões)

metabolomics
vitamins, nutraceuticals, and natural products

Condições de expedição

dry ice

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

chave InChI

NLDDIKRKFXEWBK-AWEZNQCLSA-N

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Descrição geral

[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.

Aplicação

[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

Ações bioquímicas/fisiológicas

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.

Pictogramas

Exclamation mark

Palavra indicadora

Warning

Frases de perigo

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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


Certificados de análise (COA)

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Sigma-Aldrich

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W252204

Ginger oil

6-Shogaol phyproof® Reference Substance

PHL89792

6-Shogaol

10-Gingerol phyproof® Reference Substance

PHL89203

10-Gingerol

10-Shogaol phyproof® Reference Substance

PHL83911

10-Shogaol

Biological properties of 6-gingerol: a brief review.
Wang S, et al.
Natural Product Communications, 9(7), 1027-1030 (2014)
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
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
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
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)

Artigos

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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