gingerol

Also known as 6-Gingerol, [6]-Gingerol, (S)-(6)-Gingerol, (+)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone, (S)-(+)-[6]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.

Key facts

Pepper.heat: Very hot (chemical)
Pepper.scoville: 60,000

via Wikipedia infobox

Chemical data

Formula: C17H26O4
Molecular weight: 294.4 g/mol
IUPAC name: (5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
SMILES: CCCCC[C@@H](CC(=O)CCC1=CC(=C(C=C1)O)OC)O
InChIKey: NLDDIKRKFXEWBK-AWEZNQCLSA-N
XLogP: 2.5
Polar surface area: 66.8 Å²
H-bond donors: 2
H-bond acceptors: 4
Formal charge: 0

via PubChem

Wikidata facts

Mass: 294.183109

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chemical formula: C₁₇H₂₆O₄
canonical SMILES: CCCCCC(CC(=O)CCC1=CC(=C(C=C1)O)OC)O
isomeric SMILES: CCCCC[C@@H](CC(=O)CCC1=CC(=C(C=C1)O)OC)O
Scoville grade: 60000
Commons category: Gingerols
median lethal dose (LD50): 25.5

Sources (7)

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Article

4 sections

Contents

Physiological potential
Biosynthesis
References
External links

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 is why dried ginger is more pungent than fresh ginger.