β-Caryophyllene
Identity
| Property | Value |
|---|---|
| Preferred name | β-Caryophyllene |
| IUPAC name | (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene |
| CAS number | 87-44-5 |
| PubChem CID | 5281515 [^4] |
| Chemical family | Bicyclic Sesquiterpene |
| Molecular formula | C15H24 |
| Molecular mass | 204.35 g/mol |
| Stereochemistry | Chiral; (−)-β-caryophyllene is the common natural form, and the (+)-enantiomer is a distinct identity (α-humulene, a constitutional isomer, is also kept separate) |
Aroma and sensory character
Spicy, peppery, woody, clove-like sensory notes.
Occurrence outside cannabis
- Black pepper (Piper nigrum)
- Cloves (Syzygium aromaticum)
- Hops (Humulus lupulus)
- Rosemary (Rosmarinus officinalis)
Physical properties
| Property | Value |
|---|---|
| Standard boiling point | 263 °C (atmospheric; unconfirmed by NIST) [^1] |
| Reference pressure | 101.325 kPa |
| Data source | Secondary literature; NIST WebBook (CAS 87-44-5) lists no boiling point |
Thermal-extraction context
As a 15-carbon sesquiterpene, β-caryophyllene has lower volatility and higher standard boiling temperature than 10-carbon monoterpenes.
Reported biological activity
Human evidence
No controlled human clinical trials establishing a benefit from isolated β-caryophyllene administration were identified for this archive [^2].
Animal or laboratory evidence
Receptor-binding and cell assays report that β-caryophyllene selectively binds the CB2 receptor, and preclinical rodent models report anti-inflammatory and antinociceptive activity attributed to CB2 pathways 1. Receptor-binding activity is an in vitro observation and does not constitute human clinical evidence.
Traditional or anecdotal claims
Historical black pepper remedy for respiratory and digestive comfort.
Cannabis laboratory results
Among the most abundant sesquiterpenes in cannabis flower across chemotypes; measured at 3.89–4.69 mg/g dry weight in two US hemp cultivars by validated GC-MS of hydrodistilled oil 2. Check Lab Results for COA entries.
Sources
Related pages
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Gertsch J, Leonti M, Raduner S, et al. Beta-caryophyllene is a dietary cannabinoid. Proc Natl Acad Sci USA. 2008;105(26):9099–9104. doi:10.1073/pnas.0803601105. PMID 18574142. ↩
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Joy N, et al. A Validated GC-MS Method for Major Terpenes Quantification in Cannabis sativa L. Essential Oil. 2025. PMC12670203; PMID 40042239; Booth JK, et al. Terpene synthases and terpene variation in Cannabis sativa. Plant Physiol. 2020;184(1):130–147. PMID 32591428. ↩
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