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Plant-Associated Volatile Organic Compound (VOC) Database (PVD)

A database supporting research and application of VOCs produced by plants and plant-associated microbes

(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

Metabolic Pathways

map00909
map01100
map01110

Structure

IUPAC Name

(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

PubChem CID

5281515

Synonymous Names

BETA-CARYOPHYLLENE
Caryophyllene
trans-Caryophyllene
(-)-trans-Caryophyllene
87-44-5
(-)-beta-caryophyllene
L-Caryophyllene
(-)-(E)-Caryophyllene
(E)-Caryophyllene
.beta.-Caryophyllene
b-caryophyllene
FEMA No. 2252
(E)-beta-caryophyllene
trans-beta-caryophyllene
CHEBI:10357
E-Caryophyllene
Beta-Caryophylene
trans-.beta.-Caryophyllene
(-)-Caryophyllene
.beta.-Caryophyllen
DTXSID8024739
(-)-E-Caryophyllene
(E)-beta-caryophylene
NSC 11906
NSC-11906
.beta.-(E)-Caryophyllene
UNII-BHW853AU9H
BHW853AU9H
Cannabinoid
CCRIS 8094
DTXCID304739
beta-Caryophyllen
8-Methylene-4,11,11-(trimethyl)bicyclo(7.2.0)undec-4-ene
(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
Bicyclo(7.2.0)undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)-
g-Caryophyllene
EINECS 201-746-1
C15H24
(1R,4E,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
trans-(1R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
(1R,4E,9S)-4,11,11-TRIMETHYL-8-METHYLENEBICYCLO(7.2.0)UNDEC-4-ENE
E-.beta.-caryophyllene
AI3-36121
.beta.-Caryophyllene, (-)
CHEBI:63191
2-Methylene-6,10,10-trimethylbicyclo(7.2.0)undec-5-ene
cariofileno
Tincturoid
Copaiba
8-Methylene-4,11,11-(trimethyl)bicyclo[7.2.0]undec-4-ene
caryophyllen-
clove terpenes
NSC11906
Caryophyllene B
Caryophyllene hg
beta-cariofillene
cb2 receptor
(1R,4E,9S)-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene
(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo(7.2.0)undec-4-ene
trans-(1R,9S)-4,11,11-trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene
beta-caryophillene
BICYCLO(7.2.0)UNDEC-4-ENE, 4,11,11-TRIMETHYL-8-METHYLENE-, (E)-(1R,9S)-(-)-
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (E)-(1R,9S)-(-)-
Bicyclo[7.2.0]undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)-
4,11,11-Trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene, (1R-(1R*,4E,9S))-
Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R-(1R*,4E,9S*))-
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R-(1R*,4E,9S*)]-
trans caryophyllene
caryophyllene 917
CARYOPHYLLENE ,ALPHA + BETA MIXT.
E-beta-caryophyllene
MFCD00075925
Caryophyllene, (E)
02 - Terpenes
(?)-b-caryophyllene
1-CARYOPHYLLENE
beta-(e)-caryophyllene
beta-trans-caryophyllene
clove terpene derivative
(?)-trans-Caryophyllene
caryophyllene beta natural
CARYOPHYLLENE [MI]
.beta.-trans-Caryophyllene
(-)-I(2)-caryophyllene
12 - Analysis of terpenes
CHEMBL445740
BETA-CARYOPHYLLENE [FCC]
BETA-CARYOPHYLLENE [INCI]
Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-
HY-N1415
.BETA.-CARYOPHYLLENE [FHFI]
Tox21_301497
(1S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undec-5-ene
11CAR7501
BDBM50529607
s6058
AKOS024283988
LMPR0103120001
beta-Caryophyllene, >=80%, FCC, FG
CAS-87-44-5
NCGC00142620-01
NCGC00255159-01
(-)-trans-Caryophyllene, analytical standard
CS-0016839
C09629
beta-Caryophyllene 2000 microg/mL in Acetonitrile
P198906
Q421614
W-109317
(-)-trans-Caryophyllene, >=98.5% (sum of enantiomers, GC)
Nevada Terpene Mixture 0058 1000 microg/mL in Isopropanol
8-Methylene-4,11,11-(trimethyl)bicyclo(7.2.0)undec-4-ene, (1R,4E,9S)-
BICYCLO(7.2.0)UNDEC-4-ENE, 4,11,11-TRIMETHYL-8-METHYLENE-, (1R-(1R*,4E,9S*)-
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R- (1R*,4E,9S*)]-
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R-(1R,4E,9S)]-

Formula

C15H24

Molecular Weight

204.35

Chemical Class

Sesquiterpenoid, Aliphatic, Olefin, Prenol

Reference Link

Bitas, V., McCartney, N., Li, N., Demers, J., Kim, J.-E., Kim, H.-S., et al. 2015. Fusarium Oxysporum Volatiles Enhance Plant Growth Via Affecting Auxin Transport and Signaling. Front Microbiol. 6:1248.
Suckling, D. M., Twidle, A. M., Gibb, A. R., Manning, L. M., Mitchell, V. J., Sullivan, T. E. S., et al. 2012. Volatiles from apple trees infested with light brown apple moth larvae attract the parasitoid Dolichogenidia tasmanica. J Agric Food Chem. 60:9
Cuevas, F. J., Moreno-Rojas, J. M., and Ruiz-Moreno, M. J. 2017. Assessing a traceability technique in fresh oranges (Citrus sinensis L. Osbeck) with an HS-SPME-GC-MS method. Towards a volatile characterisation of organic oranges. Food Chem. 221:1930–193
Najar-Rodriguez, A., Orschel, B., and Dorn, S. 2013. Season-long volatile emissions from peach and pear trees in situ, overlapping profiles, and olfactory attraction of an oligophagous fruit moth in the laboratory. J Chem Ecol. 39:418–29.

Plants/Microbial Species and Abiotic/Biotic Stimuli

Plant/Microbial Species	Abiotic/Biotic Stimuli
Prunus persica (Peach)	None
Malus domestica (Apple)	Insect - Epiphyas postvittana - Light Brown Apple Moth
Citrus sinensis (Sweet orange)	None
Pyrus communis (Pear)	None

Confirmed/Hypothesized Functions