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G1046

Sigma-Aldrich

[6]-Gingerol

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C17H26O4
Numéro CAS:
23513-14-6
Poids moléculaire :
294.39
Numéro MDL:
MFCD00210507
Code UNSPSC :
12352205
ID de substance PubChem :
329799719
Nomenclature NACRES :
NA.25

Niveau de qualité

200

Pureté

≥98% (HPLC)

Conditions de stockage

protect from light
under inert gas

Solubilité

methanol: 1 mg/mL, clear, colorless

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne 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

Clé InChI

NLDDIKRKFXEWBK-AWEZNQCLSA-N

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Description générale

[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

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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8-Gingerol phyproof® Reference Substance

PHL89202

8-Gingerol

USP

USP

1291504

Powdered ginger

Sigma-Aldrich

Sigma-Aldrich

W252204

Ginger oil

6-Shogaol phyproof® Reference Substance

PHL89792

6-Shogaol

Vanillylacetone ≥96%, FG

Sigma-Aldrich

W312401

Vanillylacetone

10-Gingerol phyproof® Reference Substance

PHL89203

10-Gingerol

10-Shogaol phyproof® Reference Substance

PHL83911

10-Shogaol

[6]-Gingerol dampens hepatic steatosis and inflammation in experimental nonalcoholic steatohepatitis
Tzeng TF, et al.
Phytomedicine, 22(4), 452-461 (2015)
Poovvathingal Haris et al.
International journal of biological macromolecules, 113, 124-131 (2018-02-20)
6-Gingerol [5-hydroxy-1-(4-hydroxy-3-methoxyphenyl) decan-3-one], the bio-active ingredient of the popular Indian spice ginger (Zingiber officinale Roscoe), is well-known for its pharmacological and physiological actions. The potent antioxidant, antiemetic, antiulcer, antimicrobial, analgesic, hypoglycemic, antihypertensive, antihyperlipidemic, immunostimulant, anti-inflammatory, cardiotonic, and cancer prevention activities
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
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
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