Flash Chromatographic Purification of Cannabicitran (CBCT)

Cannabicitran is one of many minor cannabinoids found in cannabis though not much is known about this compound as far as possible medicinal benefits.

What is known is that it is found in hemp strains producing high CBD content[1]. Chemically, CBCT is a diether with the same molecular weight (314) as CBD, THC, CBL, and CBC, Figure 1.

Being a diether with no phenolic groups, it is the most well retained of the cannabinoids making it relatively easy to purify and identify using reversed-phase flash chromatography.

Figure 1. Cannabicitran chemical structure. The two ether groups (-O-) are less polar than phenolic groups found in CBD and other cannabinoids enabling its increased hydrophobicity.

Since cannabicitran is extremely lipophilic, a simple reversed-phase step gradient commonly used for THC remediation (70:30 to 100:0 ethanol/water or 80:20 to 100:0 methanol/water) is very effective for its purification and isolation, Figure 2.

Figure 2. Hemp distillate purification using a methanol/water step gradient separates CBD, THC, and CBCT.

As mentioned in previous posts, automated flash chromatography systems detect and collect cannabinoids based on their ability to absorb UV light which the system supplies.  The wavelengths of UV light absorbed by each cannabinoid are different providing a means for identifying any separated/collected compound.  In the case of cannabicitran, its UV absorption wavelengths are 212 nm and 282 nm making it unique among cannabinoids and easily identified, Figure 3. 

Figure 3. UV spectrum of the cannabicitran peak show peak UV absorption maxima of 212 nm and 282 nm.

Interested in learning more about cannabinoid chromatography? Take a look at our post on purifying minor cannabinoids:

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[1] https://www.extractlabs.com/cbd-guides/what-is-cbt/