Structure Database (LMSD)

Common Name
beta-Caryophyllene
Systematic Name
Synonyms
LM ID
LMPR0103120001
Formula
Exact Mass
Calculate m/z
204.1878
Status
Curated

Classification

Biological Context

β-Caryophyllene is a sesquiterpene that has been found in plants, including C. sativa, C. indica, and hemp, and has diverse biological activities, including lipid metabolic, antioxidant, anti-neuroinflammatory, anti-proliferative, and antinociceptive properties.1,2,3,4,5,6 It is an agonist of the cannabinoid (CB) receptor CB2 (Ki = 155 nM) that inhibits cAMP production induced by forskolin in CHO-K1 cells expressing CB2 receptors (EC50 = 38 nM).7 β-Caryophyllene is also an agonist of peroxisome proliferator-activated receptor α (PPARα; EC50 = 9.58 µM in a reporter assay).2 β-Caryophyllene (1 and 2.5 µM) reduces the production of reactive oxygen species (ROS) in and protects against cytotoxicity of SH-SY5Y cells induced by 1-methyl-4-pheylpyridinium (MPP+).3 It also decreases the β-amyloid burden in the hippocampus and cerebral cortex and improves memory in an APP/PS1 transgenic mouse model of Alzheimer’s disease, decreasing the latency to find the platform in the Morris water maze during training and increasing the time spent in the target quadrant during testing when administered at a dose of 48 mg/kg per day.4 β-Caryophyllene (50 mg/kg) increases the number of entries into and the time spent in the open arms of the elevated plus maze and the time spent immobile in the forced swim test, indicating anxiolytic-like and antidepressant-like activity, effects that can be blocked by the CB2 receptor antagonist AM630 .5

This information has been provided by Cayman Chemical

References

2. Hazekamp, A., Tejkalová, K., and Papadimitriou, S. Cannabis: From cultivar to chemovar II—A metabolomics approach to Cannabis classification. Cannabis Cannabinoid Res. 1(1), 202-215 (2016).
6. Wang, G., Ma, W., and Du, J. β-Caryophyllene (BCP) ameliorates MPP+ induced cytotoxicity. Biomed. Pharmacother. 103, 1086-1091 (2018).

String Representations

InChiKey (Click to copy)
NPNUFJAVOOONJE-GFUGXAQUSA-N
InChi (Click to copy)
InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1
SMILES (Click to copy)
[C@]12([H])C(C[C@]1([H])C(=C)CCC=C(C)CC2)(C)C

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 15
Rings 2
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 238.06
Topological Polar Surface Area 0.00
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 0
logP 4.73
Molar Refractivity 66.74

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Updated at
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