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
CAS Number	58461-27-1 498-16-8 (R)-(−) 50373-53-0 (S)-(+)
3D model (JSmol)	(±): 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 CID	94060 (±) 5464156 (R)-(−) 68133 (S)-(+)
UNII	1YPC7F65XU T2QB7QHN63 (R)-(−) 8PLA23B8JZ (S)-(+)
CompTox Dashboard (EPA)	DTXSID70866690
InChI (±): 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
SMILES (±): 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
Chemical formula	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

• Lavandulyl acetate

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.
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.

External links

• Media related to Lavandulol at Wikimedia Commons