Lavandulol

Lavandulol
Names
Preferred IUPAC name
5-Methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol
Other names
2-Isopropenyl-5-methyl-4-hexen-1-ol
Identifiers
58461-27-1
3D model (Jmol) (±): Interactive image
(R)-(): Interactive image
(S)-(+): Interactive image
ChEBI CHEBI:50281
ChemSpider 84888 (±)
4576557 (R)-()
61441 (S)-(+)
ECHA InfoCard 100.055.676
EC Number 261-264-2
PubChem 94060 (±)
5464156 (R)-()
68133 (S)-(+)
UNII T2QB7QHN63 YesY
Properties
C10H18O
Molar mass 154.25 g·mol−1
Appearance Clear colorless liquid[1]
Density 0.878 g/mL at 20 °C[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Lavandulol is a monoterpene alcohol found in a variety of essential oils such as lavender oil.[3] It can exist as either of two enantiomers. The (R)-enantiomer is natural and has an aroma described as "weak floral, herbal odor with slightly lemon-like, fresh citrus fruity nuance"; the (S)-enantiomer has only a weak odor.[1]

Lavandulol and its esters are used in the perfume industry and have been identified as insect pheromones.[4][5][6]

See also

References

  1. 1 2 Sakauchi, Hiroyuki; Kiyota, Hiromasa; Takigawa, Shin-ya; Oritani, Takayuki; Kuwahara, Shigefumi (2005). "Enzymatic Resolution and Odor Description of Both Enantiomers of Lavandulol, a Fragrance of Lavender Oil". Chemistry & Biodiversity. 2 (9): 1183. doi:10.1002/cbdv.200590088.
  2. "(±)-Lavandulol". Sigma-Aldrich.
  3. "Lavandulol". Merriam-Webster.
  4. Innocenzi, PJ; Hall, DR; Cross, JV (2001). "Components of male aggregation pheromone of strawberry blossom weevil, Anthonomus rubi herbst. (Coleoptera:Curculionidae)". Journal of chemical ecology. 27 (6): 1203–18. PMID 11504023.
  5. "Semiochemical - lavandulol". pherobase.com. Retrieved 14 January 2014.
  6. Zada, A.; Dunkelblum, E.; Assael, F.; Franco, J. C.; Silva, E. B. da; Protasov, A.; Mendel, Z. (2008). "Attraction of Planococcus ficus males to racemic and chiral pheromone baits: Flight activity and bait longevity". Journal of Applied Entomology. 132 (6): 480. doi:10.1111/j.1439-0418.2008.01277.x.
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