Caryophyllene

Many plants make a special smell.

This smell comes from oils in the plants. You can find it in black pepper. It is also in cloves and rosemary. It can even be found in hops.

This smell helps give food its taste. Some people use it as a flavoring. It is safe to eat in food. It is a very common thing in nature. It is fun to smell these plants!

Caryophyllene is a natural substance found in many plants.

It is a type of sesquiterpene. This is a group of natural chemicals. You can find it in many essential oils. It helps give black pepper its smell. It is also in cloves, rosemary, and hops. It is even in basil and oregano.

Scientists study how this substance works in the body. It can act on a part of the body called a CB2 receptor. This is a special spot on certain cells. Some studies look at how it binds to these spots.

Plants make caryophyllene through a set of steps.

First, the plant uses two small parts called DMAPP and IPP. An enzyme called GPPS2 helps turn these into a new part. Then, another enzyme called IspA helps make farnesyl pyrophosphate. Finally, an enzyme called QHS1 finishes the work. This makes the caryophyllene.

The FDA says caryophyllene is safe to eat. They allow it to be used as a food additive. This means it can be used to add flavor to food. It is a very common part of nature.

Caryophyllene is a special natural substance found in many plants.

It belongs to a group of chemicals called sesquiterpenes. This molecule is quite rare because of its unique shape. It has a small four-sided ring called a cyclobutane ring. It also has a large nine-membered ring with a specific bond. These shapes help give plants their distinct smells. Many people know it from the scent of black pepper. It is also a part of many essential oils used in cooking and scents.

Plants follow a specific way it works to make this substance.

It starts with two small building blocks called DMAPP and IPP. First, an enzyme named GPPS2 helps turn these into geranyl pyrophosphate. Next, a second enzyme called IspA adds more parts. This creates a larger piece called farnesyl pyrophosphate. Finally, an enzyme called QHS1 helps the molecule fold into itself. This folding process is called intramolecular cyclization. This is how the plant finishes making the caryophyllene.

Scientists are doing basic research to see how it works in the body. They are looking at how it acts on the CB2 receptor. This is a specific spot on certain cells. Research shows it has a binding affinity of Ki = 155 nM at these receptors. This means it can attach to the receptor quite well. It has higher cannabinoid activity than its cousin, alpha-humulene. Other substances like cannabinol also bind to these same spots. Scientists compare these different strengths to learn more about how they work.

Caryophyllene is found in many different places in nature.

In cannabis flowers, it can make up 3.8% to 37.5% of the oil. It is also found in cloves at levels between 1.7% and 19.5%. Black pepper contains about 7.29% of this substance. You can find it in hops at levels from 5.1% to 14.5%. Other plants like basil and oregano also have it. Even lavender and rosemary contain these helpful molecules. It is a very widespread part of the plant world.

This substance is very safe for people to use in food. The FDA has given it a designation called GRAS. This stands for generally recognized as safe. Because of this, the FDA allows it to be a food additive. It is often used to add flavor to things we eat. When animals eat it, scientists have seen no big problems. For example, rats given large amounts for 90 days stayed healthy. It is a common and trusted part of our world.

Caryophyllene, also known as (−)-β-caryophyllene (BCP), is a natural bicyclic sesquiterpene. This means it is a chemical compound made of carbon and hydrogen with a specific, complex shape. It is found widely throughout the natural world. This molecule is quite rare because of its unique structure. It contains a cyclobutane ring, which is a small four-sided ring. It also features a trans-double bond within a nine-membered ring. These specific geometric features are uncommon in nature.

Plants create caryophyllene through a process called biosynthesis. This process uses specific building blocks called precursors. The two main precursors are dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP). First, an enzyme named GPPS2 catalyzes a reaction between these two units. This reaction involves an SN1-type process and the loss of pyrophosphate. This step creates a molecule called geranyl pyrophosphate (GPP). Next, a second enzyme called IspA facilitates a reaction with another unit of IPP. This creates farnesyl pyrophosphate (FPP). Finally, an enzyme called QHS1 triggers intramolecular cyclization. This means the FPP molecule folds into itself to form the final caryophyllene structure.

Caryophyllene is a major component in many essential oils. It is often found alongside other similar molecules. For example, it frequently exists as a mixture with isocaryophyllene. Isocaryophyllene is a cis double bond isomer. It can also be found with α-humulene. This is a ring-opened isomer of the molecule. These different versions of the chemical can change how they interact with other things.

Scientists are conducting basic research on the properties of β-caryophyllene. They are specifically studying its role as an agonist for the cannabinoid receptor type 2 (CB2 receptor). An agonist is a substance that activates a receptor. Research shows that β-caryophyllene has a binding affinity of Ki = 155 nM at these CB2 receptors. This measures how strongly the molecule attaches to the receptor. It has higher cannabinoid activity than the ring-opened isomer α-caryophyllene humulene. To understand this strength, scientists compare it to other substances. For instance, cannabinol binds to CB2 receptors with a Ki of 126.4 nM. Delta-9-tetrahydrocannabinol binds with a Ki of 36 nM.

This compound is found in a vast variety of plants at different concentrations. In cannabis sativa, it makes up between 3.8% and 37.5% of the flower essential oil. It is very prominent in Malabathrum, where it reaches 25.3%. In cloves, it accounts for 1.7% to 19.5% of the bud essential oil. Other notable amounts include 7.29% in black pepper and 5.1% to 14.5% in hops. You can also find it in basil, oregano, lavender, rosemary, and true cinnamon.

Once inside a living thing, caryophyllene undergoes metabolism. This is the process where the body breaks down or changes a substance. The metabolism of caryophyllene moves through several specific stages. First, it turns into caryophyllene oxide (C15H24O). In this stage, the alkene group becomes an epoxide. This specific oxide is what drug-sniffing dogs use to identify cannabis. From there, the process continues to 14-hydroxycaryophyllene (C15H24O). The final stage in this chain is 14-hydroxycaryophyllene oxide (C15H24O2). Researchers have even studied the X-ray crystal structure of its acetate derivative.

Safety is an important part of how we use this chemical. The FDA has given caryophyllene a "generally recognized as safe" (GRAS) designation. This allows the FDA to approve it as a food additive for flavoring. It is a common way to add aroma and taste to food products. Studies on animal safety have shown positive results. Rats given up to 700 mg/kg daily for 90 days showed no significant toxic effects. In mice, the level for toxicity was measured at 5,000 mg/kg. This demonstrates that the substance is handled safely in many applications.