Chemistry:Geranylfarnesol

From HandWiki

Geranylfarnesol is a naturally occurring irregular, long-chain, acyclic isoprenoid alcohol. This is a C
25 compound, positioned between the ubiquitous C
15 farnesol and the C
30 triterpenoid squalene in the isoprenoid biosynthesis pathway. Its chemical formula is C
25H
42O.[1] Geranylfarnesol has garnered scientific interest primarily due to its role as a key biosynthetic intermediate and its potent biological activity as an inducer of apoptosis (programmed cell death).[2]

Structure

The compound is a member of sesterterpenoid group.[3] The chemical structure consists of a linear chain of five isoprene units (C
5H
8) in a head-to-tail arrangement, terminated by a hydroxyl (—OH) group. It is the C
25 homolog of the more common C
15 isoprenoid farnesol and the direct precursor to the C
30 isoprenoid squalene. The "geranyl" prefix indicates its structural relationship to geraniol (C
10) and farnesol (C
15).

Natural occurrence

The compound was isolated from the wax of the insect Ceroplastes albolineatus via hydrolysis.[4][5] Geranylfarnesol was also isolated from sponge Fasciospongia fovea[6] and identified in the frontal glands of the termites Reticulitermes santonensis.[7]

Physical properties

Geranylfarnesol forms a colorless, viscous oil. Insoluble in water.[8]

Uses

Geranylfarnesol is known as an inducer of apoptosis in mammalian cells, often exhibiting greater potency than its shorter-chain relative, farnesol.[9] It appears to trigger the mitochondrial (intrinsic) pathway of apoptosis.[10]

See also

References

  1. ↑ "Geranylfarnesol | Chemical Substance Information | J-GLOBAL" (in en). jglobal.jst.go.jp. https://jglobal.jst.go.jp/en/detail?JGLOBAL_ID=200907090857288890. 
  2. ↑ Ríos, Tirso; C, S. Pérez (1 January 1969). "Geranylfarnesol, a new acyclic C25 isoprenoid alcohol isolated from insect wax" (in en). Journal of the Chemical Society D: Chemical Communications (5): 214–215. doi:10.1039/C29690000214. ISSN 0577-6171. https://pubs.rsc.org/en/content/articlelanding/1969/c2/c29690000214. Retrieved 5 February 2026. 
  3. ↑ Peters, K. E.; Walters, C. C.; Moldowan, J. M. (2005) (in en). The Biomarker Guide. Cambridge University Press. p. 55. ISBN 978-0-521-78158-9. https://www.google.ru/books/edition/The_Biomarker_Guide/wKkxO3QV4kAC?hl=en&gbpv=1&dq=Geranylfarnesol+density&pg=PA458&printsec=frontcover. Retrieved 5 February 2026. 
  4. ↑ Morgan, E. David (22 March 2019) (in en). Biosynthesis in Insects: Advanced Edition. Royal Society of Chemistry. p. 7-40. ISBN 978-1-78801-822-7. https://www.google.ru/books/edition/Biosynthesis_in_Insects/s7arDwAAQBAJ?hl=en&gbpv=1&dq=Geranylfarnesol&pg=SA7-PA40&printsec=frontcover. Retrieved 5 February 2026. 
  5. ↑ Reinhold, L.; Harborne, J. B.; Swain, T. (13 October 2016) (in en). Progress in Phytochemistry: Volume 4. Elsevier. p. 211. ISBN 978-1-4831-4442-9. https://www.google.ru/books/edition/Progress_in_Phytochemistry/kts_DQAAQBAJ?hl=en&gbpv=1&dq=Geranylfarnesol&pg=PA211&printsec=frontcover. Retrieved 5 February 2026. 
  6. ↑ (in en) Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Springer Science & Business Media. 6 December 2012. p. 186. ISBN 978-3-7091-8505-6. https://www.google.ru/books/edition/Fortschritte_der_Chemie_Organischer_Natu/Fjj6CAAAQBAJ?hl=en&gbpv=1&dq=Geranylfarnesol&pg=PA186&printsec=frontcover. Retrieved 5 February 2026. 
  7. ↑ Morgan, Eric David (13 July 2004) (in en). Biosynthesis in Insects. Royal Society of Chemistry. p. 107. ISBN 978-0-85404-691-1. https://www.google.ru/books/edition/Biosynthesis_in_Insects/AbXid2E-17YC?hl=en&gbpv=1&dq=Geranylfarnesol&pg=PA107&printsec=frontcover. Retrieved 5 February 2026. 
  8. ↑ "geranyl farnesol, 79577-58-5". thegoodscentscompany.com. https://www.thegoodscentscompany.com/data/rw1435241.html. 
  9. ↑ Herrmann, Wolfgang; Obeid, Rima (2011) (in en). Vitamins in the Prevention of Human Diseases. Walter de Gruyter. p. 546. ISBN 978-3-11-021448-2. https://www.google.ru/books/edition/Vitamins_in_the_Prevention_of_Human_Dise/b9ahvNjPFO8C?hl=en&gbpv=1&dq=Geranylfarnesol+Apoptosis&pg=PA546&printsec=frontcover. Retrieved 5 February 2026. 
  10. ↑ Joo, Joung Hyuck; Jetten, Anton M. (28 January 2010). "Molecular mechanisms involved in farnesol-induced apoptosis". Cancer Letters 287 (2): 123–135. doi:10.1016/j.canlet.2009.05.015. ISSN 0304-3835. https://www.sciencedirect.com/science/article/abs/pii/S030438350900367X#:~:text=rights%20and%20content-,Abstract,2%2DERK1/2%20pathway.. Retrieved 5 February 2026. 



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