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Gingerol

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Gingerol
Gingerol
Names
IUPAC name
(S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.131.126 Edit this at Wikidata
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 checkY
    Key: NLDDIKRKFXEWBK-AWEZNQCLSA-N checkY
  • 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 30-32 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Gingerol, or sometimes [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.[1] It is normally found as a pungent yellow oil, but also can form a low-melting crystalline solid.

Cooking ginger transforms gingerol into zingerone, which is less pungent and has a spicy-sweet aroma. When ginger is dried 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.[1]

Physiological effects

Gingerol may reduce nausea caused by motion sickness or pregnancy[2] and may also relieve migraine.[3]

[6]-Gingerol has been used to induce a hypothermic state in rats.[4]

Gingerol seems to be effective in an animal model of rheumatoid arthritis.[5]

Gingerol has been investigated for its effect on cancerous tumors in the bowel,[6][7] breast tissue,[8] ovaries,[9] the pancreas,[10] among other tissues, with positive results.

The product is sometimes used for gingering of horses, a practice that is seen in the horse show world, illegal in some, but not all disciplines.[11]

References

  1. ^ a b McGee, Harold (2004). "A survey of tropical spices". McGee on Food and Cooking. Hodder and Stoughton. p. 426. ISBN 0-340-83149-9.
  2. ^ Ernst, E; Pittler, MH (2000). "Efficacy of ginger for nausea and vomiting: a systematic review of randomized clinical trials". British journal of anaesthesia. 84 (3): 367–71. PMID 10793599.
  3. ^ Mustafa, T; Srivastava, K (1990). "Ginger (zingiber officinale) in migraine headache". Journal of Ethnopharmacology. 29 (3): 267–73. doi:10.1016/0378-8741(90)90037-T. PMID 2214812.
  4. ^ Ueki, S; Miyoshi, M; Shido, O; Hasegawa, J; Watanabe, T (2008). "Systemic administration of [6]-gingerol, a pungent constituent of ginger, induces hypothermia in rats via an inhibitory effect on metabolic rate". European Journal of Pharmacology. 584 (1): 87–92. doi:10.1016/j.ejphar.2008.01.031. PMID 18295202.
  5. ^ Funk, Janet L.; Frye, Jennifer B.; Oyarzo, Janice N.; Timmermann, Barbara N. (2009). "Comparative Effects of Two Gingerol-ContainingZingiber officinaleExtracts on Experimental Rheumatoid Arthritis⊥". Journal of Natural Products. 72 (3): 403–7. doi:10.1021/np8006183. PMC 2837120. PMID 19216559.
  6. ^ "Ginger 'could halt bowel cancer'". BBC News. October 29, 2003.
  7. ^ Jeong, C.-H.; Bode, A. M.; Pugliese, A.; Cho, Y.-Y.; Kim, H.-G.; Shim, J.-H.; Jeon, Y.-J.; Li, H.; Jiang, H. (2009). "[6]-Gingerol Suppresses Colon Cancer Growth by Targeting Leukotriene A4 Hydrolase". Cancer Research. 69 (13): 5584–91. doi:10.1158/0008-5472.CAN-09-0491. PMID 19531649.
  8. ^ Lee, H; Seo, E; Kang, N; Kim, W (2008). "[6]-Gingerol inhibits metastasis of MDA-MB-231 human breast cancer cells". The Journal of Nutritional Biochemistry. 19 (5): 313–9. doi:10.1016/j.jnutbio.2007.05.008. PMID 17683926.
  9. ^ Rhode, Jennifer; Fogoros, Sarah; Zick, Suzanna; Wahl, Heather; Griffith, Kent A; Huang, Jennifer; Liu, J Rebecca (2007). "Ginger inhibits cell growth and modulates angiogenic factors in ovarian cancer cells". BMC Complementary and Alternative Medicine. 7: 44. doi:10.1186/1472-6882-7-44. PMC 2241638. PMID 18096028.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  10. ^ Park, Yon Jung; Wen, Jing; Bang, Seungmin; Park, Seung Woo; Song, Si Young (2006). "[6]-Gingerol Induces Cell Cycle Arrest and Cell Death of Mutant p53-expressing Pancreatic Cancer Cells". Yonsei Medical Journal. 47 (5): 688–97. doi:10.3349/ymj.2006.47.5.688. PMC 2687755. PMID 17066513.
  11. ^ "hermographic detection of gingering in horses" T.A. Turner DVM, MS1 and R.D. Scoggins DVM, Journal of Equine Veterinary Science Volume 5, Issue 1, 1985, Pages 8-10
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