Gingerol
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| Names | |
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IUPAC name
(S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone
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| Identifiers | |
23513-14-6 
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| 3D model (Jmol) | Interactive image |
| ChEBI |
CHEBI:10136 
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| ChEMBL |
ChEMBL402978
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| ChemSpider |
391126
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| ECHA InfoCard | 100.131.126 |
| KEGG |
C10462
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| PubChem | 442793 |
| UNII |
925QK2Z900
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| Properties | |
| C17H26O4 | |
| Molar mass | 294.38 g/mol |
| Melting point | 30 to 32 °C (86 to 90 °F; 303 to 305 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is ?) |
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| Infobox references | |
| Gingerol | |
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| Heat | (SR: 60,000) |
Gingerol, properly as [6]-gingerol, is the active constituent of fresh ginger. Chemically, gingerol is a relative of capsaicin and piperine, the compounds which give chilli peppers and black pepper their respective spicyness. It is normally found as a pungent yellow oil, but also can form a low-melting crystalline solid.
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.
[6]-Gingerol administered by intraperitoneal injection has been used to induce a hypothermic state in rats.
Gingerol seems to be effective in an animal model of rheumatoid arthritis.
Gingerol and its analogues have a favourable toxicity profile, but are cytotoxic towards a range of cancer cell lines including blood cancer and lung cancer.
Gingerol has been investigated in vitro for its effect on cancerous tumors of the bowel, breast tissue, ovaries, and pancreas, with positive results.
The product is sometimes used for gingering of horses, a practice that is seen in the horse show world, and which is illegal in some, but not all disciplines.
Both ginger (Zingiber officinale) and turmeric (Curcuma longa) had been suspected to utilize phenylpropanoid pathway and produce putative type III polyketide synthase products based on the research of 6-gingerol biosynthesis by Denniff and Whiting in 1976 and by Schröder's research in 1997. 6-Gingerol is the major gingerol in ginger rhizomes and it possesses some interesting pharmacological activities like analgesic effect. While the biosynthesis of 6-gingerol is not fully elucidated, plausible pathways are presented here.
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Wikipedia