Bisabolene

Bisabolenes are a group of closely related natural chemical compounds which are classified as sesquiterpenes. Bisabolenes are produced from farnesyl pyrophosphate (FPP)^[1] and are present in the essential oils of bisabol, and of a wide variety of other plants including cubeb, lemon, and oregano. Various derivates also function as pheromones in different insects, such as stink bugs^[2] and fruit flies.^[3] Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear.^[4]

Bisabolenes

α-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	α: 17627-44-0 Y β: 495-61-4 Y γ: 495-62-5 Y
3D model (JSmol)	α: Interactive image β: Interactive image γ: Interactive image
Beilstein Reference	α: 2414203 β: 2044625 γ: 2501191
ChEBI	α: CHEBI:49244 β: CHEBI:49263 γ: CHEBI:49237
ChemSpider	α: 4509521 β: 8279897 γ: 2298446
KEGG	β: C16775
PubChem CID	α: 5352653 β: 10104370 γ: 3033866
UNII	α: SUQ209P6FX Y β: S19BRC22QA Y γ: E6941S3U3Q Y
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	204.357 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

Three isomers are known, α-, β-, and γ-bisabolene,^[5][6] which differ by the positions of the double bonds.

Uses

Bisabolenes are intermediates in the biosynthesis of many other natural chemical compounds,^[7] including hernandulcin, a natural sweetener. β-Bisabolene has a balsamic odor^[8] and is approved in Europe as a food additive.

Bisabolene has been identified as a biologically producible precursor to a diesel fuel alternative and/or cold weather additive bisabolane. ^[9]

See also

• Alpha-bisabolene synthase
• (S)-beta-bisabolene synthase
• (E)-gamma-bisabolene synthase
• (Z)-gamma-bisabolene synthase