Lavandulol

Lavandulol

Names
IUPAC name 5-Methyl-2-prop-1-en-2-ylhex-4-en-1-ol
Other names 2-Isopropenyl-5-methyl-4-hexen-1-ol
Identifiers
CAS Number	58461-27-1
ChEBI	CHEBI:50281
ChemSpider	84888 (±) 4576557 (R)-(−) 61441 (S)-(+)
EC Number	261-264-2
Jmol interactive 3D	(±): Image (R)-(−): Image (S)-(+): Image
PubChem	94060 (±) 5464156 (R)-(−) 68133 (S)-(+)
UNII	T2QB7QHN63
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	154.25 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

• 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. 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.

External links

• Media related to Lavandulol at Wikimedia Commons