Gingerol

Gingerol ([6]-gingerol) is a phenolic phytochemical compound found in fresh ginger that activates heat receptors on the tongue. 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.

Gingerol
Names
Preferred IUPAC name
(5S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
Other names
[6]-Gingerol; 6-Gingerol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.131.126
KEGG
UNII
  • 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 Y
    Key: NLDDIKRKFXEWBK-AWEZNQCLSA-N Y
  • 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
  • O=C(C[C@@H](O)CCCCC)CCc1cc(OC)c(O)cc1
Properties
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).
N verify (what is YN ?)
Infobox references
Gingerol
HeatVery hot (chemical)
Scoville scale60,000 SHU

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. This explains why dried ginger is more pungent than fresh ginger.

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

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