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G5798

Sigma-Aldrich

[10]-Gingerol

≥98% (HPLC)

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

Quality Level

100

Assay

≥98% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°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

WGK

WGK 3

Flash Point(F)

331.3 °F

Flash Point(C)

166.3 °C

Regulatory Information

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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
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.
Meran Keshawa Ediriweera et al.
Molecules (Basel, Switzerland), 25(14) (2020-07-16)
10-gingerol is a major phenolic lipid found in the rhizomes of ginger (Zingiber officinale). Being amphiphilic in nature, phenolic lipids have the ability to incorporate into cell membranes and modulate membrane properties. The purpose of the present study was to
Chien-Kei Wei et al.
International journal of molecular sciences, 18(1) (2017-01-21)
The anti-diabetic activity of ginger powder (Zingiber officinale) has been recently promoted, with the recommendation to be included as one of the dietary supplements for diabetic patients. However, previous studies presented different results, which may be caused by degradation and
Su-Chen Ho et al.
Food chemistry, 141(3), 3183-3191 (2013-07-23)
Despite the anti-neuroinflammatory capacity of ginger, the corresponding active constituents are unclear. This study analyzed the composition of fresh ginger ethanolic extract by using LC-MS. Inhibitory activities of fresh ginger extract and seven gingerol-related compounds on the neuro-inflammation were also
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