Tag Archives: extracts

Annual AOCS Meeting Spotlights Cannabinoid Analytics

By Aaron G. Biros
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The AOCS Annual Meeting is an international science and business forum on fats, oils, surfactants, lipids and related materials. The American Oil Chemist’s Society (AOCS) is holding their meeting in Orlando, Florida from April 30 to May 3, 2017. Last year’s meeting included discussions on best practices and the pros and cons of different extraction techniques, sample preparation, proficiency testing and method development, among other topic areas.

Posters on display for the duration of the Annual Meeting will discuss innovative solutions to test, preparing samples, discovering new compounds and provide novel information about the compounds found in cannabis. David Egerton, vice president of technical operations at CW Analytical (a cannabis testing laboratory in Oakland, CA), is preparing a poster titled Endogenous Solvents in Cannabis Extracts. His abstract discusses testing regulations focusing on the detection of the presence of solvents, despite the fact that endogenous solvents, like acetone and lower alcohols, can be found in all plant material. His study will demonstrate the prevalence of those compounds in both the plant material and the concentrated oil without those compounds being used in production.rsz_am17-editorialpic-cij

The conference features more than 650 oral and poster presentations within 12 interest areas. This year’s technical program includes two sessions specifically designed to address cannabinoid analytics:

Lab Proficiency Programs and Reference Samples

How do you run a lab proficiency program when you cannot send your samples across state lines? What constituents do you test for when state requirements are all different? Are all pesticides illegal to use on cannabis? What pesticides should be tested for when they are mostly illegal to use? How do you analyze proficiency results when there are no standard methods? Learn about these and other challenges facing the cannabis industry. This session encourages open and active discussion, as the cannabis experts want to hear from you and learn about your experiences.

Method Development

The need for high-quality and safe products has spurred a new interest in cannabinoid analytics, including sample preparation, pesticide, and other constituent testing. In this session, a diverse group of scientists will discuss developing analytical methods to investigate cannabis. Learn the latest in finding and identifying terpenes, cannabinoids, matrix effects, and even the best practice for dissolving a gummy bear.

Cynthia Ludwig speaking at last year's meeting
Cynthia Ludwig speaking at last year’s meeting

Cynthia Ludwig, director of technical services at AOCS, says they are making great progress in assembling analytical methods for the production of the book AOCS Collection of Cannabis Analytical Methods. “We are the leading organization supporting the development of analytical methods in the cannabis industry,” says Ludwig. “Many of the contributors in that collection will be presenting at the AOCS Annual Meeting, highlighting some of the latest advances in analyzing cannabis.” The organization hopes to foster more collaboration among those in the cannabis testing industry.

In addition to oral and poster sessions, the 2017 Annual Meeting will feature daily networking activities, more than 70 international exhibitors, two special sessions, and a Hot Topics Symposia which will address how current, critical issues impact the future of the fats and oils industry.

AOCS Highlights Cannabis Lab Standards, Extraction Technology

By Aaron G. Biros
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The American Oil Chemists’ Society (AOCS) held its annual conference in Salt Lake City this week, with a track focused on cannabis testing and technology. Cynthia Ludwig, director of technical services at AOCS and member of the advisory panel to The Emerald Test, hosted the two-day event dedicated to all things extraction technology and analytical testing of cannabis.

Highlights in the discussion surrounding extraction technologies for the production of cannabis concentrates included the diversity of concentrate products, solvent selection for different extraction techniques and the need for cleaning validation in extraction equipment. Jerry King, Ph.D., research professor at the University of Arkansas, began the event with a brief history of cannabis processing, describing the physical morphologies in different types of extraction processes.

J. Michael McCutcheon presents a history of cannabis in medicine
J. Michael McCutcheon presents a history of cannabis in medicine

Michael McCutcheon, research scientist at Eden Labs, laid out a broad comparison of different extraction techniques and solvents in use currently. “Butane is a great solvent; it’s extremely effective at extracting active compounds from cannabis, but it poses considerable health, safety and environmental concerns largely due to its flammability,” says McCutcheon. He noted it is also very difficult to get USP-grade butane solvents so the quality can be lacking. “As a solvent, supercritical carbon dioxide can be better because it is nontoxic, nonflammable, readily available, inexpensive and much safer.” The major benefit of using supercritical carbon dioxide, according to McCutcheon, is its ability for fine-tuning, allowing the extractor to be more selective and produce a wider range of product types. “By changing the temperature or pressure, we can change the density of the solvent and thus the solubility of the many different compounds in cannabis.” He also noted that, supercritical carbon dioxide exerts tremendous pressure, as compared to hydrocarbon solvents, so the extraction equipment needs to be rated to a higher working pressure and is generally more expensive.

John A. Mackay, Ph.D., left at the podium and Jerry King, Ph.D., on the right
John A. Mackay, Ph.D., left at the podium and Jerry King, Ph.D., on the right

John A. Mackay, Ph.D., senior director of strategic technologies at Waters Corporation, believes that cannabis processors using extraction equipment need to implement cleaning SOPs to prevent contamination. “There is currently nothing in the cannabis industry like the FDA CMC draft for the botanical industry,” says Mackay. “If you are giving a child a high-CBD extract and it was produced in equipment that was previously used for another strain that contains other compounds, such as CBG, CBD or even traces of THC extract, there is a high probability that it will still contain these compounds as well as possibly other contaminants unless it was properly cleaned.” Mackay’s discussion highlighted the importance of safety and health for workers throughout the workflow as well as the end consumer.

Jeffrey Raber, Ph.D., chief executive officer of The Werc Shop, examined different testing methodologies for different applications, including potency analyses with liquid chromatography. His presentation was markedly unique in proposing a solution to the currently inconsistent classification system for cannabis strains. “We really do not know what strains cause what physiological responses,” says Raber. “We need a better classification system based on chemical fingerprints, not on baseless names.” Raber suggests using a chemotaxonomic system to identify physiological responses in strains, noting that terpenes could be the key to these responses.

Cynthia Ludwig welcomes attendees to the event.
Cynthia Ludwig welcomes attendees to the event.

Dylan Wilks, chief scientific officer at Orange Photonics, discussed the various needs in sample preparation for a wide range of products. He focused on sample prep and variation for on-site potency analysis, which could give edibles manufacturers crucial quality assurance tools in process control. Susan Audino, Ph.D., chemist and A2LA assessor, echoed Wilks’ concerns over sample collection methods. “Sampling can be the most critical part of the analysis and the sample size needs to be representative of the batch, which is currently a major issue in the cannabis industry,” says Audino. “I believe that the consumer has a right to know that what they are ingesting is safe.” Many seemed to share her sentiment about the current state of the cannabis testing industry. “Inadequate testing is worse than no testing at all and we need to educate the legislators about the importance of consumer safety.”

46 cannabis laboratories participated in The Emerald Test’s latest round of proficiency testing for potency and residual solvents. Cynthia Ludwig sits on the advisory panel to give direction and industry insights, addressing specific needs for cannabis laboratories. Kirsten Blake, director of sales at Emerald Scientific, believes that proficiency testing is the first step in bringing consistency to cannabis analytics. “The goal is to create some level of industry standards for testing,” says Blake. Participants in the program will be given data sets, judged by a consensus mean, so labs can see their score compared to the rest of the cannabis testing industry. Proficiency tests like The Emerald Test give labs the ability to view how consistent their results are compared to the industry’s results overall. According to Ludwig, the results were pleasantly surprising. “The results were better than expected across the board; the vast majority of labs were within the acceptable range,” says Ludwig. The test is anonymous so individual labs can participate freely.

The AOCS cannabis working groups and expert panels are collaborating with Emerald Scientific to provide data analytics reports compliant with ISO 13528. “In the absence of a federal program, we are trying to provide consistency in cannabis testing to protect consumer safety,” says Ludwig. At the AOCS annual meeting, many echoed those concerns of consumer safety, proposing solutions to the current inconsistencies in testing standards.

Marijuana Matters

Let’s Talk CBD

By David C. Kotler, Esq.
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Let’s talk about cannabidiol, CBD, a non-psychoactive component of cannabis. Let’s not talk about CBD from the whole plant. This is a conversation about the proliferation of hemp-based CBD marketed everywhere from gas stations to specialty health and wellness stores. Heck, “its legal in all 50 states”, right?

On the Federal Level, pursuant to Title 21 USC 802 Section (16) The term “marijuana” means all parts of the plant cannabis sativa L., whether growing or not; the seeds thereof; the resin extracted from any part of such plant; and every compound, manufacture, salt, derivative, mixture, or preparation of such plant, its seeds or resin. The term does not include the mature stalks of such plant, fiber produced from such stalks, oil or cake made from the seeds of such plant, any other compound, manufacture, salt, derivative, mixture, or preparation of such mature stalks (except the resin extracted therefrom), fiber, oil, or cake, or the sterilized seed of such plant which is incapable of germination.

Proponents of the position that hemp-derived CBD is legal point to the lack of a specific definition under the above description (often asserting that their oil is not processed from the flower) and the Ninth Circuit’s opinion in Hemp Indus. Ass’n v DEA, 333 F.3d 1082 (9th Cir. 2003). They buttress their belief by citing the DEA’s clarification of hemp in the Federal Register released in October 2001 and the 2013 Farm Bills’ adoption of the following definition of industrial hemp (adopted from plant scientists research in the 70’s: “The term ‘industrial hemp’ means the plant, cannabis sativa L. and any part of such plant, whether growing or not, with a delta-9 tetrahydrocannabinol H. R. 2642—265 concentration of not more than 0.3 percent on a dry weight basis.” Much of the foregoing has been extended to even support opinions that hemp-derived CBD from domestic sources under the 2013 Farm Bill is legal for distribution nationwide.

Opponents of the hemp-derived CBD is legal argument (putting aside the issues with imported hemp and contaminants, etc.) point to the exception in the definition of “marijuana” i.e. to actually get a workable form of CBD from hemp, the preparation of the stalk puts you into the resin category which is excepted from the terms that are specifically not included in “marijuana.” In regard to HIA v. DEA cited above, opponents posit that the court decision, never mentions CBD, and the HIA maintain that this ruling did not legalize CBD.

In February 2015 and again in February 2016 the FDA issued warning letters to CBD companies. The overall context of the letters dealt with mislabeling and improper claims in addition to the most recent round of letters addressing CBD products’ exclusion from the dietary supplement definition under the FD&C act and how that is affected by CBD’s consideration as a new drug in one or more new drug applications. What has not been addressed or asserted by the FDA is the legal status of CBD under the Controlled Substances Act.

Although I have seen many commentators and attorneys opine on the legality as the case may be of hemp-derived CBD and its ability to be shipped to and sold in all 50 states (often with a caveat that readers should consult them for further advice), I have never seen the issue addressed from a practitioner that deals with the United States Patent and Trademark Office. I am not that practitioner. However, I do represent a company that has recently made application. I, not being a trademark attorney, but being sensitive to the federal government’s position collectively on CBD, found the examiner’s questions in her Office Action Letter surrounding CBD to be quite interesting. They were as follows:

  1. Do applicant’s identified goods contain marijuana, marijuana based preparations, or marijuana extracts or derivatives, synthetic marijuana, or any other illegal controlled substances?
  2. If the applicant’s goods contain Cannabidiol (CBD), is this derived from marijuana or from industrial hemp?
  3. Are the applicant’s goods lawful pursuant to the Controlled Substances Act?

I searched for another application and Office Action Letter from 2016 for another CBD product (both were vaporizer products rather than the lotions, balms, etc. that have been the subject of other applications). The questions to that applicant mirrored those above.

What I take from the questions that trademark examiners are asking is that perhaps the debate raging in academic and legal circles is for naught. It looks like at least the USPTO has resigned itself to there being a difference between cannabis or whole plant and hemp-based CBD in terms of definition and proscription under the federal controlled substances act.

So we have come full circle in my question, ‘Is it legal in all fifty states?’ If you answer yes to that question then please provide me the definition of marijuana/cannabis from the Controlled Substance Act from each of the fifty states individually and a copy of the documentation from a source showing how the industrial hemp was grown and processed and verifiable lab reports of the particular product’s contents.

Wellness Watch

Solventless Flower Oil – The Luxury Concentrate

By Dr. Emily Earlenbaugh, PhD.
7 Comments

As the high-end cannabis market continues to grow, dispensary owners and product manufactures alike seek to fill the growing niche for high-end, luxury cannabis products.

When it comes to concentrates, many people are looking to rosin to fill this luxury niche. But not all rosin is the same, and poorly processed rosin can range from a dark almost burnt tasting sap, to something that’s almost bright orange in color. A poor rosin experience can leave a bad taste in a consumer’s mouth, and discourage them from trying more in the future.

For dispensary operators looking to expand their luxury concentrates, skip the hair-straightener rosin and look for SFO. When it comes to concentrates, nothing is more luxurious than solventless flower oil (or SFO). Like most luxury items, SFO comes at a higher price point than the average gram of oil. But for those in the know, the price is well worth it.
 
What is so great about SFO?
 

Clean: Most concentrates are made using dangerous chemical solvents like butane or propane. This can leave behind toxic heavy metals. SFO is solventless. It is made using a modified Rosin process, which uses only low heat and pressure in the extraction process.

Made From Flowers: Safety is one huge bonus of the method, and I always suggest that patients and recreational users alike avoid concentrates made with solvents. But SFO is also special in that it is made directly from the flowers of the cannabis rather than the trim, hash, or kief, and the process preserves the flowers’ natural terpenes.
 
Feels Better: Terpenes are the compounds in cannabis that give it its smell and taste. Each strain has a unique smell and taste because of it’s terpenes. They also affect the feel of the strain. If you love the way sour diesel tastes and feels, but hate lemon haze, it’s probably because of the terpenes in each.
 
Terpenes can also modify the effects of THC, lessening some of its negative side effects like accelerated heart-rate, paranoia, dry mouth and mental confusion.
 
In most extraction processes, most of the flower’s natural terpenes are destroyed. If you have ever excitedly bought a concentrate of your favorite strain only to find that it doesn’t taste or feel like the flower, it is likely because the terpenes weren’t retained.  
 
Smells and Tastes Amazing: SFO has unprecedented natural terpene retention. This means it tastes incredible and feels like the flower it was made from.
 
Pressed at Low Temperatures: It’s important to note that not all Rosin is SFO. SFO is made using lower temperatures than the hair straightener and t-shirt press rosin that has flooded the market. High temperatures burn off the terpenes that make SFO so delicious. So, if you are making a purchase for your dispensary and you want a concentrate that will really knock your customer’s socks off, make sure the rosin is pressed at low temperatures and made from flower, not hash or kief.
 
Best Terpene Retention: When checking terpene analytics, beware of concentrates that have terpenes added back in. While we can isolate the terpenes we know about, we have only researched a subset of the terpenes in the cannabis plant. If we want to recreate the effect of a particular strain, we need to know all the compounds in it or the recipe won’t be right. Rosin with terpenes added back in tends to taste artificial and take on a brighter orange hue.
 
The most effective way of getting complex flavors and effects like those in the flower, is to preserve the compounds as they are in nature. That is exactly what SFO does.
 
If you are looking for that luxurious concentrate, SFO is bound to be a crowd pleaser with its potent, pleasant effects and clean, fragrant taste. Like many luxury items it is also rare, so finding a good supplier can be tricky.
 
For a great tasting SFO in CA, try out Fleurish Farm’s line of SFO. These Sonoma County rosin makers have perfected the art of terpene retention. Each flavorful option has a unique and complex aroma. And their terpene percentages are some of the highest around ranging from 3-9%.
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BEST Extractions

Busting the Myth: Examining CO2 versus Butane Extraction

By John A. Mackay, Ph. D.
26 Comments
jMackaypic

The basis of anecdotal controversy continues about the use of hydrocarbons versus carbon dioxide. It is important to note that hydrocarbons span a range of phases on the planet earth.

It is important to eliminate the cost of the instruments and the cost of the facilities from this comparison to keep the discussion on specifically the extraction principles.

Source: (https://en.wikipedia.org/wiki/Butane#Isomers)
Source: (https://en.wikipedia.org/wiki/Butane#Isomers)

Butane is a gaseous hydrocarbon. As you add more carbons to hydrocarbons, they move from gaseous to liquid.

It is also important to note that the same is true of carbon dioxide in its natural form on the earth’s atmosphere, it is a gas. It is nonflammable and used in fire extinguishers.

At typical conditions, carbon dioxide in the supercritical range is similar to hexane (C6H14) and ethyl acetate in its solubility characteristics. Propane (C3H8) and butane (C4H10) are gases at normal atmospheric conditions. Both must be manipulated for the extraction of CBDA and CBD. For example, both CO2 and C4H10 must be placed under pressure and then passed through the material to extract the lipophilic terpenes and cannabinoids.

For this short discussion, let’s remove the concern about the different volatilities of the compounds. Hydrocarbons with a spark will be significantly more powerful of an explosion than carbon dioxide (note it could be used to put out the butane fire). The hydrocarbons can be in more configurations and therefore the getting the correct form initially is critical. For example, butane can have all the carbons in a row like a train, or branched like a tree. Those are very different and have different characteristics too. Getting pharmaceutical grade butane is essential to ensure safety. The concern that people have expressed with butane is what is in the other 0.1% for 99.9%. Checking for residual butane is less of a concern than the polyaromatic hydrocarbons in the untested cylinder. Furthermore, in the wrong hands it can be more volatile.

Source: (https://en.wikipedia.org/wiki/Carbon_dioxide)
Source: (https://en.wikipedia.org/wiki/Carbon_dioxide)

The critical premise that needs to be considered is the final formulation. Is one solvent significantly more applicable than the other? No. They have different characteristics.

Propane is a common solvent in the spices, flavors and fragrances industry. For example, the extraction of lipids and oils from vegetables and the fatty oils from seeds, it would be an advantage to have a solvent that is totally miscible, i.e. will be totally soluble in a fluid. This is similar to the idea of sugar in hot water versus in water in ice. If an example of cardamom were used comparing CO2 and propane (which is similar to butane), the pressure needed for CO2 would be 100 bar, while propane would be only 20 bar. However the increasing the pressure of the propane from 20 to 50 bar at a constant 25 C, also increases the chlorophyll from 3.4 g/g oil to 10.8 g/g oil. Meanwhile with the more finely tunable CO2 from 80 to 100 to 200 the amount of chlorophyll is negligible (0.36 g/g oil) but at 300 bar it dramatically increases to 4.53 g/g oil.

Additionally the CO2 is a better extraction for the terpenes in the cardamom. The beta-pinine, Cineole, linalool, alpha-terpinol and bornelole. The increase in the propane pressure will allow us to increase the yield of the CO2 (Illes, V, et. al. Proceedings of the Fifth Meeting of Supercritical Fluids, Nice, France, Tome 2, 555-560).

This example is the same with the butane and cannabis. Butane is a stronger solvent and if left too long will continue to pull out more and more polar compounds like chlorophyll. With the fine-tuning of CO2, you can eliminate or you can pull out the chlorophyll if you choose the wrong conditions.

So fast extractions are possible with butane but little control of all the material, while CO2 can be tunable and therefore is able to collect all of the same material, just through a segmented process.