Caryophyllene

Caryophyllene, also known as (−)-β-caryophyllene, is a natural bicyclic sesquiterpene found in various essential oils. It is especially prevalent in clove oil, extracted from the stems and flowers of Syzygium aromaticum (cloves), Cannabis sativa, rosemary, and hops. Typically, it is found mixed with isocaryophyllene and α-humulene (α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for its cyclobutane ring and a trans-double bond in a 9-membered ring, both rare in nature.

Profile:

• 📂 CAS N° 13877-93-5

• ⚖️ MW — 204.35 g/mol

• 📝 Odour Type: Terpenic

• 📈 Odour Strength: medium

• 👃🏼 Odour Profile: woody - spicy, dry and tenacious odor. Many descriptions include the clove-like word, since it is found also in Clove leaf. The dry down presents a pleasantly musty driftwood note. While there is an ostensibly tenacious open, the longevity is only about 3-4 hours, making this unmistakably a top note.

• 👅 Flavor Profile: Dry-woody, somewhat bitter taste. Is true that there is a similarity to Clove leaf oil, but that oil does contain Caryophyllene and includes it in its odor picture. Spicy pepper-like, woody, camphoraceous, with a citrus background.

• ⚗️ Uses: Occasionally used in perfume compositions, but the modem derivatives of Caryophyllene are more and more preferred. See the following two monographs. Used in flavour compositions, mainly in spice blends and particularly for chewing gum, where concentrations may be as high as 200 ppm. It also acts as a fixative for the more volatile spice chemicals such as Cinnamic aldehyde, etc. Recommended use up to 8% in fragrance concentrate.

Discovery

The first total synthesis of caryophyllene in 1964 by E.J. Corey was a landmark achievement in synthetic organic chemistry. Caryophyllene is one of the compounds that contribute to the spiciness of black pepper.

Natural Occurrence

Caryophyllene is found in various plants and essential oils, including:

• Cannabis, hemp, marijuana (Cannabis sativa): 3.8–37.5% of cannabis flower essential oil

• Black caraway (Carum nigrum): 7.8%

• Cloves (Syzygium aromaticum): 1.7–19.5% of clove bud essential oil

• Hops (Humulus lupulus): 5.1–14.5%

• Basil (Ocimum spp.): 5.3–10.5% O. gratissimum; 4.0–19.8% O. micranthum

• Oregano (Origanum vulgare): 4.9–15.7%

• Black pepper (Piper nigrum): 7.29%

• Lavender (Lavandula angustifolia): 4.62–7.55% of lavender oil

• Rosemary (Rosmarinus officinalis): 0.1–8.3%

• Cinnamon (Cinnamomum zeylanicum): 6.9–11.1%

• Malabathrum (Cinnamomum Tamala): 25.3%

• Ylang-ylang (Cananga odorata): 3.1–10.7%

• Copaiba oil (Copaifera spp.)

Production

Caryophyllene is produced by isolating it from clove leaf oil, clove stem oil, or cinnamon leaf oil. It is also obtained from certain fractions of American pine oil. It should be noted that caryophyllene is not exclusively β-caryophyllene and may often carry an unpleasant off-odour of sulfuraceous character from sulfate turpentine and other sources.

Sources:

• National Center for Biotechnology Information (2020). PubChem Compound Summary for CID 5322111. Retrieved November 25, 2020 from https://pubchem.ncbi.nlm.nih.gov/compound/5322111.