Chemistry:Geranyl-linalool
Geranyl-linalool is a naturally occurring organic compound classified as a diterpenoid with the molecular formula C
20H
34O.[1] This is a compound found in various plants and serves as an important intermediate in the biosynthesis of several biologically active compounds.
Chemical structure
Geranyl-linalool is classified as an acyclic alyphatic diterpenoid polyalkene alcohol.[2] The compound includes four isoprene units arranged in a head-to-tail fashion, characteristic of diterpenes.[3]
Natural occurrence
Geranyllinalool is found in various plant species, including: tobacco (Nicotiana tabacum)[4] where it was first identified, ginkgo (Ginkgo biloba), various orchid species, some fungi and marine organisms. The compound is typically present in trace amounts and is often detected through careful phytochemical analysis.
Biosynthesis
Geranyl-linalool is biosynthesized via the plastidial MEP pathway. The compound is formed from geranylgeranyl diphosphate (GGPP) through the action of specific terpene syntheses.[5] The compound serves as a precursor to various cyclic diterpenes and other biologically active compounds in plants. In tobacco, geranyl-linalool is part of the cembranoid diterpene pathway and can be further metabolized into various oxidation products.[6]
Physcal properties
The compound forms a colorless to pale yellow liquid which is insoluble in water, but soluble in organic solvents.
Uses
Geranyl-linalool is commonly used as a fragrance.[7] Its aroma is mild and described as "floral, rose, balsamic".[8] It also demonstrate insecticidal property to xylophagous insects and pine wood. The compound has also been studied for its influence on pyocyanin and Pseudomonas quinolone signal production by Pseudomonas aeruginosa. Geranyl-linalool can also be used as a precursor in the synthesis of teprenone by reacting with acetylated Meldrum's acid.[9]
References
- ↑ "1,6,10,14-Hexadecatetraen-3-ol, 3,7,11,15-tetramethyl-, (E,E)-" (in en). NIST. https://webbook.nist.gov/cgi/cbook.cgi?ID=C1113219.
- ↑ Tisserand, Robert; Young, Rodney (2 December 2013) (in en). Essential Oil Safety: A Guide for Health Care Professionals. Elsevier Health Sciences. p. 569. ISBN 978-0-7020-5434-1. https://books.google.com/books?id=DbEKAQAAQBAJ&dq=Geranyl-linalool&pg=PA569. Retrieved 4 March 2026.
- ↑ Dev, Sukh (1985) (in en). CRC Handbook of Terpenoids--Diterpenoids: Tetracyclic and pentacyclic diterpenoids. CRC Press. p. 30. ISBN 978-0-8493-3604-1. https://books.google.com/books?id=IX86AQAAIAAJ&q=Geranyl-linalool. Retrieved 4 March 2026.
- ↑ Tie, Jinxin; Li, Shitou; He, Wenmiao; Li, Yongsheng; Liao, Fu; Xue, Jingjing; Bai, Bing; Yang, Jing et al. (15 June 2024). "Study of metabolite differences of flue-cured tobacco from Canada (CT157) and Yunnan (Yunyan 87)". Heliyon 10 (11). doi:10.1016/j.heliyon.2024.e32417. ISSN 2405-8440. https://pmc.ncbi.nlm.nih.gov/articles/PMC11219350/#:~:text=The%20analysis%20results%20are%20shown,predominantly%20pyridine%20and%20quinoline%20compounds.. Retrieved 5 March 2026.
- ↑ Liao, Zhihua; Chen, Min; Gong, Yifu; Guo, Liang; Tan, Qiumin; Feng, Xiaoqi; Sun, Xiaofen; Tan, Feng et al. (April 2004). "A New Geranylgeranyl Diphosphate Synthase Gene from Ginkgo biloba , which Intermediates the Biosynthesis of the Key Precursor for Ginkgolides". DNA Sequence 15 (2): 153–158. doi:10.1080/10425170410001667348. https://www.researchgate.net/publication/8362120_A_New_Geranylgeranyl_Diphosphate_Synthase_Gene_from_Ginkgo_biloba_which_Intermediates_the_Biosynthesis_of_the_Key_Precursor_for_Ginkgolides. Retrieved 5 March 2026.
- ↑ Falara, Vasiliki; Alba, Juan M.; Kant, Merijn R.; Schuurink, Robert C.; Pichersky, Eran (September 2014). "Geranyllinalool synthases in solanaceae and other angiosperms constitute an ancient branch of diterpene synthases involved in the synthesis of defensive compounds". Plant Physiology 166 (1): 428–441. doi:10.1104/pp.114.243246. ISSN 1532-2548. PMID 25052853.
- ↑ Lapczynski, A.; Bhatia, S. P.; Letizia, C. S.; Api, A. M. (1 November 2008). "Fragrance material review on geranyl linalool". Food and Chemical Toxicology 46 (11, Supplement): S176–S178. doi:10.1016/j.fct.2008.06.050. ISSN 0278-6915. PMID 18640234. https://www.sciencedirect.com/science/article/abs/pii/S0278691508003402. Retrieved 4 March 2026.
- ↑ "(E)-geranyl linalool". Scents and Flavors. https://scentsandflavors.com/database/9dbb5197-6209-4531-85a6-20ebfd16e22d.
- ↑ "Geranyllinalool". Sigma Aldrich. https://www.sigmaaldrich.com/RU/en/product/aldrich/48809?srsltid=AfmBOopt8yL1UQAMpPBBIT2FIcNC1UukcfyuARGq30KYwD7pwiyOpJ3n.
 |  |
