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G5798

Sigma-Aldrich

[10]-Gingerol

≥98% (HPLC)

Synonym(s):

(S)- 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-tetradecanone, 10-Gingerol

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About This Item

Empirical Formula (Hill Notation):
C21H34O4
CAS Number:
23513-15-7
Molecular Weight:
350.49
MDL number:
MFCD01682694
UNSPSC Code:
85151701
PubChem Substance ID:
329799946
NACRES:
NA.25

Assay

≥98% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

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

InChI

1S/C21H34O4/c1-3-4-5-6-7-8-9-10-18(22)16-19(23)13-11-17-12-14-20(24)21(15-17)25-2/h12,14-15,18,22,24H,3-11,13,16H2,1-2H3/t18-/m0/s1

InChI key

AIULWNKTYPZYAN-SFHVURJKSA-N

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General description

[10]-Gingerol is a pungent, non-volatile phenolic compound of fresh ginger root.

Application

[10]-Gingerol has been used as an antibacterial agent to study its effects on Escherichia coli ATP synthase. It has also been used as an anti-hyperglycemic agent to test its effects on promoting glucose utilization in 3T3-L1 adipocytes and C2C12 myotubes.

Biochem/physiol Actions

[10]-Gingerol is a potent anti-cancer agent and a known inhibitor of breast cancer cells growth by blocking cell proliferation and inducing programmed cell death. It also inhibits ovarian cancer cells growth by inducing G2 phase cell cycle arrest. 10-Gingerol elicits inhibitory effects towards triple breast cancer cells in both mouse models and in vitro studies. It also displays anti-neuroinflammatory and anti-hyperglycemic activities.
[10]-Gingerol is a bioactive compound found in ginger (Zingiber officinale) with anti-inflammatory and antioxidant activity.

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

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

331.3 °F - closed cup

Flash Point(C)

166.3 °C - closed cup

Certificates of Analysis (COA)

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Andrea Rasmussen et al.
Advanced pharmaceutical bulletin, 9(4), 685-689 (2019-12-21)
Purpose: Gingerol homologs found in the rhizomes of ginger plants have the potential to benefit human health, including the prevention and treatment of cancer. This study evaluated the effect of 10-gingerol on ovarian cancer cell (HEY, OVCAR3, and SKOV-3) growth.
Megan M Bernard et al.
Experimental and molecular pathology, 102(2), 370-376 (2017-03-21)
The ginger rhizome is rich in bioactive compounds, including [6]-gingerol, [8]-gingerol, and [10]-gingerol; however, to date, most research on the anti-cancer activities of gingerols have focused on [6]-gingerol. In this study, we compared [10]-gingerol with [8]-gingerol and [6]-gingerol in terms
Zhufeng Wu et al.
The Journal of pharmacy and pharmacology, 67(4), 583-596 (2014-12-17)
To determine the reaction kinetics for regioselective glucuronidation of gingerols (i.e. 6-, 8- and 10-gingerol) by human liver microsomes and expressed UDP-glucuronosyltransferase (UGT) enzymes, and to identify the main UGT enzymes involved in regioselective glucuronidation of gingerols. The rates of

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