Wikipedia

Geranyl-linalool

Geranyl-linalool
Names
IUPAC name
(6E,10E)-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraen-3-ol
Other names
  • Geranyllinalool
  • Geranyl linalool
  • (E,E)-geranyllinalool
  • 3,7,11,15-Tetramethyl-1,6,10,14-hexadecatetraen-3-ol
Identifiers
3D model (JSmol)
6713421
ChEBI
ChemSpider
EC Number
  • 214-201-8
KEGG
UNII
  • InChI=1S/C20H34O/c1-7-20(6,21)16-10-15-19(5)14-9-13-18(4)12-8-11-17(2)3/h7,11,13,15,21H,1,8-10,12,14,16H2,2-6H3/b18-13+,19-15+ ☒N
    Key: IQDXAJNQKSIPGB-HQSZAHFGSA-N
  • CC(=CCC/C(=C/CC/C(=C/CCC(C)(C=C)O)/C)/C)C
Properties
C20H34O
Molar mass 290.491 g·mol−1
Appearance pale yellow liquid
Density 0.9 g/cm3
Boiling point 389.9 °C (733.8 °F; 663.0 K)
insoluble
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Flash point 124.4 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Geranyl-linalool is a naturally occurring organic compound classified as a diterpenoid with the molecular formula C20H34O.[2] This is a compound found in various plants and serves as an important intermediate in the biosynthesis of several biologically active compounds.

Chemical structure

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Geranyl-linalool is classified as an acyclic alyphatic diterpenoid polyalkene alcohol.[3] The compound includes four isoprene units arranged in a head-to-tail fashion, characteristic of diterpenes.[4]

Natural occurrence

[edit]

Geranyllinalool is found in various plant species, including: tobacco (Nicotiana tabacum)[5] 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

[edit]

Geranyl-linalool is biosynthesized via the plastidial MEP pathway. The compound is formed from geranylgeranyl diphosphate (GGPP) through the action of specific terpene syntheses.[6] 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.[7]

Physcal properties

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The compound forms a colorless to pale yellow liquid which is insoluble in water, but soluble in organic solvents.

Uses

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Geranyl-linalool is commonly used as a fragrance.[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

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  1. ^ PubChem. "Geranyllinalool". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-03-04.
  2. ^ "1,6,10,14-Hexadecatetraen-3-ol, 3,7,11,15-tetramethyl-, (E,E)-". NIST. Retrieved 4 March 2026.
  3. ^ Tisserand, Robert; Young, Rodney (2 December 2013). Essential Oil Safety: A Guide for Health Care Professionals. Elsevier Health Sciences. p. 569. ISBN 978-0-7020-5434-1. Retrieved 4 March 2026.
  4. ^ Dev, Sukh (1985). CRC Handbook of Terpenoids--Diterpenoids: Tetracyclic and pentacyclic diterpenoids. CRC Press. p. 30. ISBN 978-0-8493-3604-1. Retrieved 4 March 2026.
  5. ^ Tie, Jinxin; Li, Shitou; He, Wenmiao; Li, Yongsheng; Liao, Fu; Xue, Jingjing; Bai, Bing; Yang, Jing; Wu, Jizhong (15 June 2024). "Study of metabolite differences of flue-cured tobacco from Canada (CT157) and Yunnan (Yunyan 87)". Heliyon. 10 (11): e32417. doi:10.1016/j.heliyon.2024.e32417. ISSN 2405-8440. Retrieved 5 March 2026.{{cite journal}}: CS1 maint: article number as page number (link) CS1 maint: unflagged free DOI (link)
  6. ^ Liao, Zhihua; Chen, Min; Gong, Yifu; Guo, Liang; Tan, Qiumin; Feng, Xiaoqi; Sun, Xiaofen; Tan, Feng; Tang, Kexuan (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. Retrieved 5 March 2026.
  7. ^ 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. PMC 4149726. PMID 25052853.
  8. ^ 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. Retrieved 4 March 2026.
  9. ^ "Geranyllinalool". Sigma Aldrich. Retrieved 4 March 2026.