Gingerol

Structural formula
General
Surname	Gingerol
other names	( S ) -5-Hydroxy-1- (4-hydroxy-3-methoxy-phenyl) -decan-3-one ( IUPAC )
Molecular formula	C 17 H 26 O 4
Brief description	yellowish, odorless liquid
External identifiers / databases
EC number	607-241-6
ECHA InfoCard	100.131.126
PubChem	442793
ChemSpider	391126
Wikidata	Q421081
properties
Molar mass	294.39 g mol −1
Physical state	liquid
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 301-315-319-335
	P: 261-301 + 310-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Gingerol is an important flavor component of ginger rhizome ( Zingiber officinale ). Gingerol is the main cause of the pungent taste of ginger.

Related substances

Ginger rhizome

So far, six pungent substances have been identified in ginger. Further ingredients with structures similar to the pungent substances are 6-, 8-, 10-gingerol and 6-, 8-, 10-shogaol. 6-Shogaol is a breakdown product of 6-Gingerol, whereby Gingerol loses a hydroxyl group . Zingiberen and zingiberol are also contained in ginger and are important for the taste .

Analytics

For the reliable qualitative and quantitative determination of gingerol in various test materials, the coupling of HPLC with mass spectrometry is suitable after adequate sample preparation .

effect

On the one hand, it is believed that gingerols, especially shogaols, act on the vanilloid receptor and thus trigger an anti-inflammatory reaction. It could be shown that the pungent substances (gingerol, shogaol) have a specific influence on the interleukin / cytokine pattern . The interleukin / cytokine pattern can be used to see different reactions to a disease.

It could also be shown that the pungent substances influence the iNOS (inducable NO synthase ), which may have an impact on the smooth muscles and thus cause a constriction or dilation of the vessels .

Individual evidence

↑ Data gingerol (PDF) at Carl Roth , accessed on 14 December of 2010.
↑ ^a ^b ^c ^d data sheet 6-Gingerol from Sigma-Aldrich , accessed on April 3, 2011 ( PDF ).
↑ Entry on spicy taste. In: Römpp Online . Georg Thieme Verlag, accessed on July 19, 2014.
^ Y. Tao, W. Li, W. Liang, RB Van Breemen: Identification and quantification of gingerols and related compounds in ginger dietary supplements using high-performance liquid chromatography-tandem mass spectrometry. In: J Agric Food Chem. 57 (21), Nov 11, 2009, pp. 10014-10021. PMID 19817455 .
↑ C. Schoenknecht, G. Andersen, P. Schieberle: A novel method for the quantitation of gingerol glucuronides in human plasma or urine based on stable isotope dilution assays. In: J Chromatogr B Analyt Technol Biomed Life Sci. 1036-1037, Nov 15, 2016, pp. 1-9. PMID 27700987 .
↑ S. Lee, C. Khoo, CW Halstead, T. Huynh, A. Bensoussan: Liquid chromatographic determination of 6-, 8-, 10-gingerol, and 6-shogaol in ginger (Zingiber officinale) as the raw herb and dried aqueous extract. In: J AOAC Int. 90 (5), Sep-Oct 2007, pp. 1219-1226. PMID 17955965 .
↑ Tzung-Yan Leea, Ko-Chen Leeb, Shih-Yuan Chena, Hen-Hong Chang: 6-Gingerol inhibits ROS and iNOS through the suppression of PKC-α and NF-κB pathways in lipopolysaccharide-stimulated mouse macrophages. In: Biochemical and Biophysical Research Communications. Volume 382, No. 1, April 24, 2009, pp. 134-139.

[roth-1] Data gingerol (PDF) at Carl Roth , accessed on 14 December of 2010.

[Sigma-2] ta sheet 6-Gingerol from Sigma-Aldrich , accessed on April 3, 2011 ( PDF ).

[roempp-3] Entry on spicy taste. In: Römpp Online . Georg Thieme Verlag, accessed on July 19, 2014.

[4] Y. Tao, W. Li, W. Liang, RB Van Breemen: Identification and quantification of gingerols and related compounds in ginger dietary supplements using high-performance liquid chromatography-tandem mass spectrometry. In: J Agric Food Chem. 57 (21), Nov 11, 2009, pp. 10014-10021. PMID 19817455 .

[5] C. Schoenknecht, G. Andersen, P. Schieberle: A novel method for the quantitation of gingerol glucuronides in human plasma or urine based on stable isotope dilution assays. In: J Chromatogr B Analyt Technol Biomed Life Sci. 1036-1037, Nov 15, 2016, pp. 1-9. PMID 27700987 .

[6] S. Lee, C. Khoo, CW Halstead, T. Huynh, A. Bensoussan: Liquid chromatographic determination of 6-, 8-, 10-gingerol, and 6-shogaol in ginger (Zingiber officinale) as the raw herb and dried aqueous extract. In: J AOAC Int. 90 (5), Sep-Oct 2007, pp. 1219-1226. PMID 17955965 .

[7] Tzung-Yan Leea, Ko-Chen Leeb, Shih-Yuan Chena, Hen-Hong Chang: 6-Gingerol inhibits ROS and iNOS through the suppression of PKC-α and NF-κB pathways in lipopolysaccharide-stimulated mouse macrophages. In: Biochemical and Biophysical Research Communications. Volume 382, No. 1, April 24, 2009, pp. 134-139.