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G1046

[6]-Gingerol

≥98% (HPLC)

Synonym(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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Pack SizeSKUAvailabilityPrice
5 mg
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$304.00
10 mg
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$588.00

About This Item

Empirical Formula (Hill Notation):
C17H26O4
CAS Number:
23513-14-6
Molecular Weight:
294.39
NACRES:
NA.25
PubChem Substance ID:
329799719
UNSPSC Code:
12352205
MDL number:
MFCD00210507

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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

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[1]

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.

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This Item
50866PHL8920101514
[6]-Gingerol ≥98% (HPLC)

Sigma-Aldrich

G1046

[6]-Gingerol

[6]-Gingerol analytical standard

Supelco

50866

[6]-Gingerol

6-Gingerol phyproof® Reference Substance

PHL89201

6-Gingerol

[8]-Gingerol analytical standard

Supelco

01514

[8]-Gingerol

assay

≥98% (HPLC)

assay

≥94.0% (HPLC)

assay

≥90.0% (HPLC)

assay

≥95.0% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care

application(s)

food and beverages

application(s)

food and beverages

Quality Level

200

Quality Level

100

Quality Level

-

Quality Level

100

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

solubility

methanol: 1 mg/mL, clear, colorless

solubility

-

solubility

-

solubility

-

storage condition

protect from light, under inert gas

storage condition

-

storage condition

-

storage condition

-

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pictograms

Exclamation mark
GHS07

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

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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Certificates of Analysis (COA)

Lot/Batch Number
0000519740
0000519740
0000500806
0000500806
0000466745

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Articles

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.

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.
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
View All Related Papers

Global Trade Item Number

SKUGTIN
G1046-5MG04061833624913
G1046-10MG04061833624906

Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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