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
CAS Number	58461-27-1;
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	T2QB7QHN63 ;
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
Density	0.878 g/mL at 20 °C
	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]

References

^ ^a ^b 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.
^ "(±)-Lavandulol". Sigma-Aldrich.
^ "Lavandulol". Merriam-Webster.
^ 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.
^ "Semiochemical - lavandulol". pherobase.com. Retrieved 14 January 2014.
^ 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

[Sakauchi-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.

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[5]

[6]

See also

References

External links