Gingerol

Gingerol
Gingerol
Heat	Very hot (chemical)
Scoville scale	60,000 SHU

Gingerol
Names
	Preferred IUPAC name (5S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
	Other names [6]-Gingerol; 6-Gingerol
Identifiers
CAS Number	23513-14-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:10136 ;
ChEMBL	ChEMBL402978 ;
ChemSpider	391126 ;
ECHA InfoCard	100.131.126
KEGG	C10462 ;
PubChem CID	442793;
UNII	925QK2Z900 ;
CompTox Dashboard (EPA)	DTXSID3041035 ;
	InChI 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 Key: NLDDIKRKFXEWBK-AWEZNQCLSA-N ; InChI=1/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 Key: NLDDIKRKFXEWBK-AWEZNQCLBF;
	SMILES O=C(C[C@@H](O)CCCCC)CCc1cc(OC)c(O)cc1;
Properties
Chemical formula	C17H26O4
Molar mass	294.38 g/mol
Melting point	30 to 32 °C (86 to 90 °F; 303 to 305 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Gingerol ([6]-gingerol) is a phenolic phytochemical compound found in fresh ginger that activates heat receptors on the tongue.^[1]^[2] It is normally found as a pungent yellow oil in the ginger rhizome, but can also form a low-melting crystalline solid. This chemical compound is found in all members of the Zingiberaceae family and is high in concentrations in the grains of paradise as well as an African Ginger species.

Cooking ginger transforms gingerol via a reverse aldol reaction into zingerone, which is less pungent and has a spicy-sweet aroma. When ginger is dried or mildly heated, gingerol undergoes a dehydration reaction forming shogaols, which are about twice as pungent as gingerol.^[3] This explains why dried ginger is more pungent than fresh ginger.^[4]

Ginger also contains [8]-gingerol, [10]-gingerol,^[5] and [12]-gingerol,^[6] collectively deemed gingerols.

^ Mao QQ, Xu XY, Cao SY, Gan RY, Corke H, Beta T, Li HB (May 2019). "Zingiber officinale Roscoe)". Foods. 8 (6): 185. doi:10.3390/foods8060185. PMC 6616534. PMID 31151279.
^ Yin, et al. (17 June 2019). "Structural mechanisms underlying activation of TRPV1 channels by pungent compounds in gingers". British Journal of Pharmacology. 176 (17): 3364–3377. doi:10.1111/bph.14766. PMC 6692589. PMID 31207668.
^ NSF International Determination of Gingerols and Shogaols in Zingiber officinale rhizome and powdered extract by High-Performance Liquid Chromatography ^{[full citation needed]}
^ McGee, Harold (2004). "A survey of tropical spices". McGee on Food and Cooking. Hodder and Stoughton. p. 426. ISBN 0-340-83149-9.
^ Zick SM, Djuric Z, Ruffin MT, Litzinger AJ, Normolle DP, Alrawi S, et al. (August 2008). "Pharmacokinetics of 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol and conjugate metabolites in healthy human subjects". Cancer Epidemiology, Biomarkers & Prevention. 17 (8): 1930–6. doi:10.1158/1055-9965.EPI-07-2934. PMC 2676573. PMID 18708382.
^ Park M, Bae J, Lee DS (November 2008). "Antibacterial activity of [10]-gingerol and [12]-gingerol isolated from ginger rhizome against periodontal bacteria". Phytotherapy Research. 22 (11): 1446–9. doi:10.1002/ptr.2473. PMID 18814211. S2CID 31384218.

[1] Mao QQ, Xu XY, Cao SY, Gan RY, Corke H, Beta T, Li HB (May 2019). "Zingiber officinale Roscoe)". Foods. 8 (6): 185. doi:10.3390/foods8060185. PMC 6616534. PMID 31151279.

[2] Yin, et al. (17 June 2019). "Structural mechanisms underlying activation of TRPV1 channels by pungent compounds in gingers". British Journal of Pharmacology. 176 (17): 3364–3377. doi:10.1111/bph.14766. PMC 6692589. PMID 31207668.

[nsf-3] NSF International Determination of Gingerols and Shogaols in Zingiber officinale rhizome and powdered extract by High-Performance Liquid Chromatography ^{[full citation needed]}

[mcgee-4] McGee, Harold (2004). "A survey of tropical spices". McGee on Food and Cooking. Hodder and Stoughton. p. 426. ISBN 0-340-83149-9.

[5] Zick SM, Djuric Z, Ruffin MT, Litzinger AJ, Normolle DP, Alrawi S, et al. (August 2008). "Pharmacokinetics of 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol and conjugate metabolites in healthy human subjects". Cancer Epidemiology, Biomarkers & Prevention. 17 (8): 1930–6. doi:10.1158/1055-9965.EPI-07-2934. PMC 2676573. PMID 18708382.

[6] Park M, Bae J, Lee DS (November 2008). "Antibacterial activity of [10]-gingerol and [12]-gingerol isolated from ginger rhizome against periodontal bacteria". Phytotherapy Research. 22 (11): 1446–9. doi:10.1002/ptr.2473. PMID 18814211. S2CID 31384218.

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