December 19, 2021

What Are Phenols & What’re They Doin’ In My CBD?

As you might know by now, cannabis is a crazy complex plant. Perhaps this is why CBD has so many — and such diverse — potential health and wellness benefits.

Clinicians, researchers, consumers, producers, and enthusiasts alike are curious to unlock the mysteries and magic of CBD. With CBD legal across the land, investigation of the industrial hemp plant is accelerating and accumulating.

One of the cannabis’s secrets that’s starting to come into the light is that of phenols. In this post, reveal what these phytochemicals are, their amazing capabilities, and how they tie in to your favorite CBD gummies and CBD tinctures.

Phenols 101

Assuming you’re not a PhD chemist, we’ll kick off with the basics — like what are phenols?

Phenols, aka phenolics, are organic chemical compounds. Found in most flora and fauna, they’re especially abundant in plants. Interestingly, though phenols don’t really do anything for plants themselves, they’re exceptionally healthful for the animals that consume them.

The hallmark of these compounds is their specific molecular structure that includes “an aromatic ring with one or more hydroxyl groups.”(1) If a substance has a single phenolic group — it’s a simple phenol. If a substance has multiple phenolic groups — it’s a polyphenol. Phenolic compounds contribute to a plant’s color, flavor, and smell.

Phenols vs Phenol

A point of clarification may help you get through the rest of this article. Phenol, phenolics, phenols, polyphenols, and phenolic compounds (PCs) are related but not all the same.(2) It goes like this:

  • Phenols, phenolics, phenolic compounds. These are phenolic substances with molecular structures that have at least one of those aforementioned hydroxyl group attached to an aromatic ring.
  • Polyphenols. These are phenolic substances with molecular structures that feature more than one hydroxyl group attached to an aromatic ring. There are more than 10,000 chemical compounds sauntering around with a sash that says “Polyphenol” on it.(3)
  • Phenol. This is a specific type of phenolic that’s also known as carbolic acid. In its purest state, phenol may be colorless or white with slightly sweet odor.(4) While it’s acidic and toxic in its pure form, tiny amounts of phenol — incorporated into household, personal care, and cosmetic goods — are generally not harmful. Phenol is also used in a variety of medical, scientific, and commercial applications.

Yes, maybe a taaaaad confusing…. But hopefully a little clearer than mud now. The key things to remember are:

  1. This post focuses on phenols — as in phenolics, phenolic compounds, polyphenols. We’ll use the terms phenols, phenolic compounds, and PCs interchangeably here on out.
  2. Phenols have a unique molecular shape. This shape has ramifications — it affects how these compounds work with other substances and within our bodies.(5) We’ll come back to this later.

Kinds Of Phenols

There are several categories of phenols, phenolic compounds, and their derivatives. These include:

  • Flavonoids
  • Lignanamides
  • Phenol amides
  • Phenolic acids
  • Stilbenes
  • Terpenes

Each class — and the individual substances that are under its umbrella — has its own traits. Which brings us to…

Benefits Of Phenols

Phenols can do your bod a world of good. They’ve been proven to be very “anti”:

  • Antioxidant
  • Anti-cancer
  • Antibacterial
  • Anti-inflammatory
  • Antimutagenic

Across the board, phenols are touted as powerful antioxidants. However, different kinds of phenols may provide a different mix of health benefits than the next type. For example, flavonoids are reputed for their anti-inflammatory abilities, whereas stilbenes are acclaimed for their cancer-fighting properties. Luckily, you’ll likely get an array of phenols with the plants you consume.

Phenolic Compounds In Cannabis

You’ve heard, haven’t you? Cannabis is a plant! This means it’s pulsing with phenols from root’s end to leaf’s tip.

Phenols are naturally created in cannabis. Through internal processing steps — collectively referred to as biosynthesis — the plant converts various phytochemicals into phenols.(6)

Are Cannabinoids Phenolic Compounds?

Technically, yes. Cannabinoids are a type of phenol known as terpeno-phenolic compounds. And, you probably already guessed this, but this breed of phenolics is only found in cannabis.

Non-Cannabinoid Phenolic Compounds In Cannabis

Previous blog posts have dwelled (rightly so!) on the characteristics and benefits of cannabinoids. So here we’ll spotlight the “other” phenols in cannabis.

Phenol Types Found in Cannabis

The primary categories of non-cannabinoid PCs in cannabis include:(7,8,9)

  • Alkaloids
  • Flavonoids
  • Lignanamides
  • Phenol amides
  • Phenolic acids
  • Stilbenes
  • Terpenes

Regardless of class, all phenols are highly-bioactive and health-protective plant-based nutrients.

Some Phenols in Cannabis

As of 2021, there are at least 42 identified non-cannabinoid phenolic compounds in cannabis.(7) Because of exciting new discoveries related to phenols and other substances in cannabis — it’s likely that research will continue on this path and even more PCs will be found.

So, what phenols are partying in your cannabis? If you look closely (just take our word for it), you'll see these PCs shakin' their groove things:(3,9,10)

  • Apigenin
  • 3,3′-demethyl-heliotropamide
  • Apigenin-7-O-glucoside
  • Caffeic acid
  • Caffeoyl tyramine
  • Caflanone
  • Cannabisin A
  • Cannabisin B
  • Cannabisin C
  • Cannabisin D
  • Cannflavin A
  • Cannflavin B
  • Catechin
  • Chlorogenic acid
  • Denbinobin
  • Epicatechin
  • Ferulic acid
  • Flavanone
  • Flavonol
  • Hydroxycinnamic acids
  • Kaempferol
  • Kaempferol-3-O-glucoside
  • Luteolin
  • Luteolin-7-O-glucoside
  • Naringenin
  • N-trans-caffeoyltyramine
  • P-coumaric acid
  • Phloroglucinol
  • Quercetin
  • Quercetin-3-glucoside
  • Resorcinol
  • Rutin

Some phenols in CBD can be found in other plants, but many of them only exist in cannabis. By extension, their special properties and benefits are also only available via cannabis. What a perfect transition to discussing…

Benefits Of Non-Cannabinoid PCs

Not only are scientists searching for phenolic substances themselves, they’re eagerly exploring what they do.

Several studies and articles assert that the dynamic duo of CBD + Phenols has been shown to bring about many wellness benefits, like:( 3,9,11,12)

  • One small-scale dog study revealed that a short course of CBD can influence metabolism. Researchers deduced that the phenols in the CBD contributed to significant changes associated with metabolic biomarkers (e.g., levels of substances like amino acids, glucose, and vitamins).
  • Phenolics such as cannabidiol can kill cancer cells.
  • Flavonoids are anti-cancer, antioxidant, antithrombogenic, antidiabetic, antiviral, and neuroprotective and rehabilitative. They can help address certain ocular disorders and be therapeutic for conditions like viral hepatitis, malaria, and autoimmune disorders. The flavonoid caflanone demonstrated anti-coronavirus effects. (Fun fact: Cannflavin A is considered to be 30x more effective than aspirin at inhibiting inflammation!)
  • Lignanamides and phenolic amides are cytotoxic, antineoplastic, anti-inflammatory, anti-obesity, analgesic, antihyperlipidemic, and antihyperlipidemic. They may also support cardiovascular health.
  • Stilbenes and their derivatives combat cancer and tumors, inhibit platelet aggregation, and fight free radicals. There’s evidence that they might help with pancreatitis and HIV.
  • Polyphenols in cannabis are able to modulate several enzymes and exhibit cardio- or chemo-protective qualities.

One last thing, as if you needed more convincing of the benefits of CBD and phenols. It appears (according to loads of studies, anecdotes, etc.) that nutraceuticals are safer, more bioavailable (especially if leveraging nanotechnology!), and have fewer side effects than traditional Rx drugs.(9) Plus, the blend of CBD and PCs may produce an entourage effect and actually alleviate side effects from other treatments.(13) So there.

A couple broader takeaways from the research that you can ponder:

  1. CBD, tag-teaming with its glorious phenols, may present new and unique treatment opportunities for health concerns.
  2. We may be a bit closer to understanding the pathways via which CBD works its wellness wonders.
  3. Revelationary research begets more research, which leads to even more possibilities for innovative therapies to improve mental and physical well-being.

Harnessing The Power Of Phenolic Compounds In Your CBD

Many factors — like environmental conditions, cultivar, cultural and postharvest practices, processing conditions, storage, etc. — can affect the phenolic load in a cannabis plant and the downstream CBD oil.

If you’re going through the trouble (it’s really no trouble at all…) to access the might of phenols and CBD — you might as well get the most out of your efforts. Here are some things to pay attention to when shopping for phenol-rich CBD products.

Age & Anatomy Matter

Not all cannabis plants — or parts of the plants — contain equal quantities of phenols.

A study from 2018 determined that cannabis extracts from younger plants have higher levels of PCs and more antioxidant activity.(14)

Other research concluded that different parts of the plant have different concentrations of phenols. For instance, inflorescences (the flower clusters) have a phenol content that’s 10 to 100 times greater than other parts of the plant.(9)

We also know that female hemp plants have larger stores of CBD. (Don’t know that? Read Anatomy Of CBD or CBD Sex Ed next.)

So, it stands to reason that a CBD oil derived from the inflorescences of a juvenile girl plant would have more phenolics than one created from an elderly boy plant’s leaves. Capisce?

Processing Methods Matter

The handling of the cannabis plant and its byproducts can impact to quantity and quality of the phenols.

The extraction method a processor uses will affect the amount of phenols retained in the finished CBD extract.(14) Extraction and processing can also damage PCs, which may reduce their efficacy and bioavailability.

Phenols are best preserved with gentler processing techniques, such as CO2 extraction. “Softer touch” production practices safeguard the integrity phenolic compounds and may result in higher PC yields. Bonus: They tend to be more eco-friendly and produce a healthier and safer CBD oil extract.(8) For a deep dive into this, check out What Is CO2 Extraction & Why's It A Good Thing For My CBD?.

Product Selection Matters

The concentration and bioavailability of phenols varies depending upon the species of cannabis and the form of CBD.

Cannabis sativa L. is a good source of polyphenols for nutraceutical or supplementation purposes. However, each cultivar (breed or strain) has its own bespoke ratios of phenols.(9) So, it may take a little research to find cannabis products made from the strain that are especially high in the phenols you desire.

Your choice of CBD type can also impact the phenol load in your product.

  • Isolate CBD has been processed to strip out everything but the CBD. CBD products made with isolate won’t have any phenolic compounds other than the pure CBD.
  • Full- and broad-spectrum CBD maintain a salad bowl of phytocompounds, including all the innate phenols. If you want the bennies of phennies — go with one of these CBD varieties.

Lastly, it’s good to consider the non-CBD ingredients and where everything originates from. In general, better growing conditions (e.g., more nutrients in the soil, favorable growing conditions, fewer toxins or pesticides, etc.). may yield more phenol dense crops. Similarly, better ingredients may mean more/higher quality PCs.

CBD Phenols Are Phenol-menal

Phenols are naturally-occurring substances common to plants. Cannabis contains many varieties of phenolic compounds, several of which are unique to cannabis. Cannabinoids — like CBD — are a type of phenol, too.

Like other plant nutrients, phenols serve up an astounding array of health benefits. Among other things, phenols are powerful antioxidants and anti-inflammatories. They’ve also been shown to help with cancer, metabolic conditions, coronavirus, and more.

As always, do your research before buying CBD. If you want to get the most phenolic bang for your buck, select CBD oil products made:

  • From cannabis plants that feature the phenolic profile that best matches your needs
  • Using a CO2 extraction method

EXPERIENCE THE BENEFITS OF PHENOLS FOR YOURSELF

References

  1. (n.d.). Phenolic Compound. Science Direct. https://doi.org/10.1016/b0-12-227055-x/01178-0
  2. Kougan, GB, et al. (2013). Simple Phenols, Phenolic Acids, and Related Esters from the Medicinal Plants of Africa. Medicinal Plant Research in Africa. https://doi.org/10.1016/B978-0-12-405927-6.00006-0
  3. Lowe, H, et al. (2021). Non-Cannabinoid Metabolites of Cannabis sativa L. with Therapeutic Potential. Plants. https://doi.org/10.3390/plants10020400
  4. Jewell, T. (2018). What are the Medical and Health Uses for Phenol? Healthline. https://www.healthline.com/health/what-is-phenol
  5. Borges, R, et al. (2013). Understanding the Molecular Aspects of Tetrahydrocannabinol and Cannabidiol as Antioxidants. Molecules. https://doi.org/10.3390/molecules181012663
  6. Rea, KA, et al. (2019). Biosynthesis of cannflavins A and B from Cannabis sativa L. Phytochemistry. https://doi.org/10.1016/j.phytochem.2019.05.009
  7. Radwan, MM, et al. (2021). Cannabinoids, Phenolics, Terpenes and Alkaloids of Cannabis. Molecules. https://doi.org/10.3390/molecules26092774
  8. Isidore, E, et al. (2021). Extraction of Phenolic Compounds and Terpenes from Cannabis sativa L. By-Products: From Conventional to Intensified Processes. Antioxidants. https://doi.org/10.3390/antiox10060942
  9. Izzo, L, et al. (2020). Analysis of Phenolic Compounds in Commercial Cannabis sativa L. Inflorescences Using UHPLC-Q-Orbitrap HRMS. Molecules. https://doi.org/10.3390/molecules25030631
  10. Sakakibara, I, et al. (1992). Three phenyldihydronaphthalene lignanamides from fruits of Cannabis sativa. Phytochemistry. https://doi.org/10.1016/0031-9422(92)83479-i
  11. Morris, EM, et al. (2021). Alteration of the Canine Metabolome After a 3-Week Supplementation of Cannabidiol (CBD) Containing Treats: An Exploratory Study of Healthy Animals. Frontiers in Veterinary Science. https://doi.org/10.3389/fvets.2021.685606
  12. Olivas-Aguirre, M, et al. (2020). Phenolic Compounds Cannabidiol, Curcumin and Quercetin Cause Mitochondrial Dysfunction and Suppress Acute Lymphoblastic Leukemia Cells. International Journal of Molecular Sciences. https://doi.org/10.3390/ijms22010204
  13. Federica, P, et al. (2018). Cannabis Phenolics and their Bioactivities. Current Medicinal Chemistry. https://doi.org/10.2174/0929867324666170810164636
  14. Drinić, Z, et al. (2018). Effect of extraction solvent on total polyphenols content and antioxidant activity of Cannabis sativa L. Lekovite Sirovine. https://doi.org/10.5937/leksir1838017d


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