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 Registry Number	17627-44-0 (α) ; 495-61-4 (β) ; 495-62-5 (γ)
ChemSpider	4509521 (α); 8279897 (β); 2298446 (γ)
	InChI 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- (α) ; 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 (β) ; 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+ (γ) ;
Jmol-3D images	Image (α); Image (β); Image (γ)
	SMILES CC1=CCC(/C(C)=C/C/C=C(C)/C)CC1 (α) ; CC1=CC[C@@H](C(CC/C=C(C)/C)=C)CC1 (β) ; CC(CC/1)=CCC1=C(C)/CC/C=C(C)/C (γ) ;
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]

Uses[edit]

Bisabolenes are intermediates in the biosynthesis of many other natural chemical compounds,^[3] including hernandulcin, a natural sweetener. β-Bisabolene has a balsamic odor^[4] and is approved in Europe as a food additive.

References[edit]

^ 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.
^ 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.
^ Bisabolene derived sesquiterpenoid biosynthesis
^ (−)-β-bisabolene, flavornet.org

External links[edit]

Beta-bisabolene, NIST Chemistry WebBook listing

[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] Bisabolene derived sesquiterpenoid biosynthesis

[4] (−)-β-bisabolene, flavornet.org

[1]

[2]

[3]

[4]

Bisabolene

Uses[edit]

References[edit]

External links[edit]

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Names
α-Bisabolene
β-Bisabolene
β-Bisabolene
γ-Bisabolene
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 Registry Number	17627-44-0 (α)^N 495-61-4 (β)^N 495-62-5 (γ)^N
ChemSpider	4509521 (α) 8279897 (β) 2298446 (γ)
InChI 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- (α) 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 (β) 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+ (γ)
Jmol-3D images	Image (α) Image (β) Image (γ)
SMILES CC1=CCC(/C(C)=C/C/C=C(C)/C)CC1 (α) CC1=CC[C@@H](C(CC/C=C(C)/C)=C)CC1 (β) CC(CC/1)=CCC1=C(C)/CC/C=C(C)/C (γ)
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