Bisabolene

Bisabolenes

α-Bisabolene
β-Bisabolene
β-Bisabolene
γ-Bisabolene
Names
IUPAC names (α): (E)-1-Methyl-4-(6-methylhepta-2,5-dien-2-yl)cyclohex-1-ene (β): (S)-1-Methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene (γ): (Z)-1-Methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene
Identifiers
CAS Number	17627-44-0 (α) 495-61-4 (β) 495-62-5 (γ)
3D model (Jmol)	(α): Interactive image (β): Interactive image (γ): Interactive image
ChemSpider	4509521 (α) 8279897 (β) 2298446 (γ)
InChI (α): InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6-8,15H,5,9-11H2,1-4H3/b14-7- (β): InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,15H,4-5,7,9-11H2,1-3H3/t15-/m1/s1 (γ): InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8H,5,7,9-11H2,1-4H3/b15-14+
SMILES (α): CC1=CCC(/C(C)=C/C/C=C(C)/C)CC1 (β): CC1=CC[C@@H](C(CC/C=C(C)/C)=C)CC1 (γ): CC(CC/1)=CCC1=C(C)/CC/C=C(C)/C
Properties
Chemical formula	C15H24
Molar mass	204.36 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bisabolenes are a group of closely related natural chemical compounds which are classified as sesquiterpenes. Bisabolenes are present in the essential oils of a wide variety of plants including cubeb, lemon and oregano. Various derivates also function as pheromones in different insects, such as stink bugs^[1] and fruit flies.^[2] It has also been observed to be produced by several fungi, though it's biological role in that group of organisms remains unclear.^[3]

Uses

Bisabolenes are intermediates in the biosynthesis of many other natural chemical compounds,^[4] including hernandulcin, a natural sweetener. β-Bisabolene has a balsamic odor^[5] and is approved in Europe as a food additive.

References

1. Aldrich, J.R.; Numata, H.; Borges, M.; Bin, F.; Waite, G.K.; Lusby, W.R. (1993). "Artifacts and pheromone blends from Nezara spp. and other stink bug (Heteroptera: Pentatomidae)". Zeitschrift für Naturforschung. 48C: 73–79.
2. Lu, F.; Teal, P.E. (2001). "Sex pheromone components in oral secretions and crop of male Caribbean fruit flies, Anastrepha suspensa (Loew)". Arch Insect Biochem Physiol. 48 (3): 144–154. doi:10.1002/arch.1067.
3. Spakowicz, Daniel J.; Strobel, Scott A. (2015). "Biosynthesis of hydrocarbons and volatile organic compounds by fungi: bioengineering potential". Applied microbiology and biotechnology. 99 (12): 4943–4951. Retrieved 2016-02-22.
4. Bisabolene derived sesquiterpenoid biosynthesis Archived November 2, 2010, at the Wayback Machine.
5. (−)-β-bisabolene, flavornet.org

External links

• Beta-bisabolene, NIST Chemistry WebBook listing