L-Caryophyllene
[CAS# 87-44-5]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Hydrocarbon spice >> Olefin
• Name: L-Caryophyllene
• Synonyms: trans-Caryophyllene; trans-beta-Caryophyllene; beta-Caryophyllen; beta-Caryophyllene; (-)-trans-Caryophyllene; (-)-beta-Caryophyllene; (1R,4E,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• CAS Registry Number: 87-44-5
• EC Number: 201-746-1
• SMILES: C/C/1=CCCC(=C)[C@H]2CC([C@@H]2CC1)(C)C

Properties

• Density: 0.89
• Boiling point: 268 °C
• Refractive index: 1.499
• Flash point: 105 °C

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H304-H317
• Safety Statements: P261-P272-P280-P301+P316-P302+P352-P321-P331-P333+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Aspiration hazard	Asp. Tox.	1	H304
Skin sensitization	Skin Sens.	1B	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

The discovery of L-caryophyllene dates back to the early 1800s, when scientists began to isolate and study essential oils. Beta-caryophyllene was first isolated from clove oil by German chemist Friedrich Wilhelm Sertürner in the early 19th century. Later, its chemical structure was elucidated as C15H24, which features a bicyclic structure with a cyclobutane ring—uncommon in natural compounds.

L-caryophyllene is a colorless to pale yellow liquid with a woody, spicy odor. Its structure includes double bonds and a unique cyclobutane ring that contributes to its stability and reactivity. This sesquiterpene is able to interact with cannabinoid receptors in the human body, which further distinguishes it from other terpenes and is particularly attractive for therapeutic uses.

L-caryophyllene is widely used in the flavor and fragrance industry for its rich aroma and ability to enhance the flavor of various food and beverage products. Its spicy, peppery flavor adds depth to savory dishes, sauces, and marinades. In the fragrance industry, its warm, woody scent is an important ingredient in formulating perfumes, colognes, and aromatherapy products, adding to their sophistication and appeal.

In addition to its sensory contributions, L-caryophyllene has antimicrobial properties that help preserve the freshness and quality of food products. This makes it a beneficial addition to natural food preservation strategies.

The most promising application of L-caryophyllene is its potential therapeutic function. It has anti-inflammatory properties due to its interaction with the CB2 cannabinoid receptor. Unlike THC (tetrahydrocannabinol), L-caryophyllene does not produce psychoactive effects, making it a safe anti-inflammatory and analgesic option.

Research suggests that L-caryophyllene may help manage pain by modulating inflammatory responses and interacting with pain receptors. This makes it a hot topic for the development of natural pain relief alternatives, especially for conditions such as arthritis and neuropathic pain.

Preliminary research suggests that L-caryophyllene may have anxiolytic and antidepressant effects. By affecting the endocannabinoid system, it helps relieve symptoms of anxiety and depression and promotes mental health without the side effects associated with traditional treatments.

Its role in protecting the gastrointestinal tract from inflammation and oxidative stress has also gained attention, opening avenues for its use in treating conditions such as inflammatory bowel disease (IBD) and other gastrointestinal disorders.

In agriculture, L-caryophyllene is a natural insect repellent. Its strong aroma repels a variety of insects, reducing the need for synthetic pesticides and promoting sustainable agricultural practices.

Plants produce L-caryophyllene as part of their defense mechanism against herbivores and pathogens. Understanding its role in plant biology could help develop crop varieties with enhanced resistance to pests and diseases.

References

2025. Investigation of the in vitro effects of cannabidiol, cannabidiolic acid, and the terpene β-caryophyllene on lymphocytes harvested from atopic and healthy dogs: A preliminary study. Research in Veterinary Science.
DOI: 10.1016/j.rvsc.2024.105483

2024. Select terpenes from Cannabis sativa are antinociceptive in mouse models of post-operative pain and fibromyalgia via adenosine A2a receptors. Pharmacological reports : PR.
DOI: 10.1007/s43440-024-00687-1

2008. Beta-caryophyllene is a dietary cannabinoid. Proceedings of the National Academy of Sciences, 105(26).
DOI: 10.1073/pnas.0803601105