Lavandulol

Lavandulol is a monoterpene alcohol found in a variety of essential oils such as lavender oil.[3] The term refers to 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
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.055.676
EC Number
  • 261-264-2
UNII
  • (±): InChI=1S/C10H18O/c1-8(2)5-6-10(7-11)9(3)4/h5,10-11H,3,6-7H2,1-2,4H3
    Key: CZVXBFUKBZRMKR-UHFFFAOYSA-N
  • (R)-(−): InChI=1S/C10H18O/c1-8(2)5-6-10(7-11)9(3)4/h5,10-11H,3,6-7H2,1-2,4H3/t10-/m0/s1
    Key: CZVXBFUKBZRMKR-JTQLQIEISA-N
  • (S)-(+): InChI=1S/C10H18O/c1-8(2)5-6-10(7-11)9(3)4/h5,10-11H,3,6-7H2,1-2,4H3/t10-/m1/s1
    Key: CZVXBFUKBZRMKR-SNVBAGLBSA-N
  • (±): CC(=CCC(CO)C(=C)C)C
  • (R)-(−): CC(=CC[C@@H](CO)C(=C)C)C
  • (S)-(+): CC(=CC[C@H](CO)C(=C)C)C
Properties
C10H18O
Molar mass 154.253 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 and its esters are used in the perfume industry and have been identified as insect pheromones.[4][5][6]

See also

References
  1. 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): 1183–6. doi:10.1002/cbdv.200590088. PMID 17193200. S2CID 36611254.
  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. doi:10.1023/A:1010320130073. PMID 11504023. S2CID 40743068.
  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. hdl:10400.5/5591. S2CID 1141741.
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