Alcademics

I've been reading the word "terpenes" a lot lately and a pitch on a terpene turbocharged tequila finally gave me the push I needed to learn what the heck they are. 

Terpenes are any of a class of monocyclic hydrocarbons of the formula C10H16, obtained from plants. [source]

Any of numerous hydrocarbons (C5H8)n found especially in essential oils, resins, and balsams [source]

Terpenes are a large and diverse class of organic compounds, produced by a variety of plants, particularly conifers, and by some insects. They often have a strong odor and may protect the plants that produce them by deterring herbivores and by attracting predators and parasites of herbivores.... Terpenes are the major components of rosin and of turpentine produced from resin... Terpenes and terpenoids are the primary constituents of the essential oils of many types of plants and flowers. [source]

This story on SevenFifty Daily has information about terpenes in wine. 

Of all the aroma compounds found in wine, terpenes seem to get the most attention and study. There’s something inherently alluring about the floral, rose, citrus, pine, and mint aromas most often associated with this group of compounds. Petrol and pepper are also a part of the greater family, adding to the olfactory diversity.

All grapes have terpenes—some bursting with them, others in quantities below sensory threshold, where they still may work synergistically with other compounds to affect aroma in indirect ways. There are more than 4,000 terpenes in the natural world, but only around 75 have been identified in grapes, and a few dozen in wine.

Most terpene-related wine conversations focus on what are known as monoterpenes (think floral, rose, and citrus) that are just one part of a diverse family of aroma compounds called isoprenoids.

 

So terpenes are aromatic compounds - but why are they springing up all of a sudden in all my nerdy news feeds?

Weed. Weed is why. Terpenes/terpenoids are present in cannabis and there is some attention to them of late. 

What's up with terpenes and cannabis? 

This website did a good job at explaining it to me:

Simply put, terpenes are what gives an orange its citrusy smell. They give pine trees their unique aroma. They’re even responsible for the relaxing effects in lavender. They are chemicals that determine how things smell.

But wait. You thought that cannabinoids were the compounds in the cannabis plant that caused healing, right? Yes, but it’s been discovered that terpenes can play a big role in that as well. In fact, cannabinoids and terpenes work together in something called the entourage effect.

The entourage effect simply means that cannabinoids such as THC and CBD, along with the hundreds of other compounds, along with the terpenes, are meant to work together. It’s the whole plant that does the best job, not just a single compound. While relief does come from using a CBD oil or a THC oil, whole plant therapy has been the most common use. Utilizing all the compounds and terpenes in the plant may just be the best way after all.

Terpenes can intensify or downplay the effects of the cannabinoids. Have you ever noticed how two similar strains can produce profoundly different effects? One may leave you with couch lock and the other may energize you? That’s another aspect of the entourage effect, which is driven by both cannabinoids and terpenes.

I also found this video to be very interesting - it covers both what terpenes are and how they are extracted in cannabis. 

I am not going to spend any more time learning about terpenes and cannabis but this video makes me think that products made with cannabis (and as we'll see later, agave) terpenes are meant to pair with and perhaps enhance isolated THC and CBD cannabinoids. 

Terpenes and Agave

Back to booze. So I was intrigued by the sciencey press release for a new tequila called El Sativo. I wouldn't have paid it any mind (sounds like pseudo-science) except for the fact that the tequila won best tequila in the San Francisco World Spirits Competition, of which I am a judge. Is their special terpene-maximizing process the reason why it tastes so good? 

That's what got me started down this road. The brand sent me a list of active terpenes with their supposed medical applications (lavender aroma relaxes you, pinene is anti-inflammatory, limonene is antibacterial, etc). So first I wanted to learn about terpenes in tequila and then about how this brand is supposedly upping the terpene content. 

I found this paper: 

Biological activities of Agave by-products and their possible applications in food and pharmaceuticals

Agave leaves are considered a by-product of alcoholic beverage production (tequila, mezcal and bacanora) because they are discarded during the production process, despite accounting for approximately 50% of the total plant weight. These by-products constitute a potential source of Agave extracts rich in bioactive compounds, such as saponins, phenolic compounds and terpenes, and possess different biological effects, as demonstrated by in vitro and in vivo tests (e.g. antimicrobial, antifungal, antioxidant, anti-inflammatory, antihypertensive, immunomodulatory, antiparasitic and anticancer activity). Despite their positive results in biological assays, Agave extracts have not been widely evaluated in food systems and pharmaceutical areas, and these fields represent a potential route to improve the usage of Agave plants as food additives and agents for treating medical diseases.
© 2017 Society of Chemical Industry

So I approached the brand with skepticism but an open mind and asked some questions. El Sativo describes its brand/process using the following language: 

El Sativo’s co-creators and fourth-generation family of distillers use an innovative distillation process that captures and accentuates the agave plant’s own natural benefits. “These terpenes, found in the agave, have a myriad of health benefits, including mood-lifting and energy-boosting attributes, which is why we transformed our distillation process in order to help maintain their properties,” states co-founder Dr. Robert Summers.

Using small batch stone ovens, the blue agaves are slowly steamed for 24-48 hours, using no diffusers nor autoclaves.

There are naturally occurring plant benefits found in the agave known to boost energy and mood while reducing inflammation for a much better drinking experience. We pull out these particular raw ingredients prior to cooking and maintain until distillation. This improves the molecular structure, a marvel of stimulated tequila.

It is made at  NOM 1480 that also makes 40 other brands. The brand provided more information on terpenes when I asked (sorry about the formatting):

Scientific studies demonstrate that terpenes have physical and mental health benefits,
and the possibility of further discovery into these compounds for human health and wellbeing are endless and exciting. These
benefits are supported by several in-vitro and clinical trials, and as regulations surrounding
cannabis lessen, scientists are carrying out more research into the possible health benefits
including: anti-depressant, anti-inflammatory, anti-oxidant, anti-cancer, analgesic, anticonvulsive, anti-tumor, neuroprotective, anti-mutagenic, anti-allergic, antiseptic, antibiotic,
anti-diabetic, digestive, and diuretic, among many others.

Terpenes do not get you “high,” although they are associated
with Cannabinoids, such as tetrahydrocannabinol (THC). While they
have been known to activate receptors in the body’s
endocannabinoid system, terpenes influence them differently and
have no psychotropic properties. Unknowingly, it is likely you consume
terpenes daily, and they quietly enhance your wellness. Terpenes do
not have any euphoric effect like THC does, but they do however have
the ability to change the way you feel. Many terpenes such as linalool
have a calming, sedative effect; limonene is known to increase
sharpness and enhance a positive mood, while pinene has been
discovered to aid in memory retention and may help boost pulmonary
function.

The Company and its Cannabis Connection

Prior to creating El Sativo Tequila, several members of our team
developed a medical cannabis company in Nevada, so we had a
connection and prior knowledge of terpenes and how they contribute
to health and wellness. Our team of doctors and scientists extracted,
isolated, and studied the effects of cannabinoids on patients for years.

How It's Made

El Sativo sets itself apart by utilizing a special distillation method that naturally
highlights the Agave plant’s precious resources. Terpenes are naturally occurring
plant compounds found in the agave and known to support energy and mood
while reducing inflammation. We isolate these compounds and maintain them
throughout the distillation process.

I Had Many Questions

So after reading all of this, I did much of the research cited above and found it interesting, even if I'm extremely hesitant to assign any beneficial functional properties to tequila because distilled spirits at full strength are not health drinks. 

I also found that you can just buy a 3-pound jug of agave terpenes to make tequila-flavored things! (Its description is: ""Highly" Concentrated, 100% Agave Terpenes are used as a natural flavor adjunct in Craft Beer, Spirits and other specialty applications where agave flavors, aromas are desired.")

I was mad I had wasted my time. But I got some answers, and they say it's not the same thing. 

What is different about El Sativo’s process vs using a jug of agave terpenes? (Note: all quotes attributed to Dr. Robert Summers)

Those jugs of agave terpenes are most likely concentrated flavor syrups which may contain sugars, carbons, metals along with terpenes and flavonoids. Those are meant to enhance flavor.

In formulating our tequila, we use an extraction process which is environmentally friendly. We use CO2 and pressure to bring the raw ingredients to a 'critical’ mass, which transforms it into a liquid and yields the terpenes. We then use a further distillation process, to isolate the terpene molecule.

Our process is not about extracting the essential oils of the plant, which contain flavonoids, polyphenols, and other compounds, which make up the plant’s flavor as a nectar. Rather, we isolate the particular mono-terpenes that we want to focus on, relative to their benefits (mood lifters, energy boosters, anti-inflammatories). Through our distillation, it’s solely about the benefits and not the flavors.

Extraction Process and Flavor Impact

All terpenes degrade with increased time and temperature as well as exposure to the elements. We take extra care to ensure minimal degradation throughout our proprietary distillation process. Additionally, the boiling point is different for each individual terpene which can range from 246-350 degrees Fahrenheit, so we are mindful of this throughout the process.

In combination, the terpenes may have an entourage effect, meaning they interact with each other to increase benefits. After we figured out which isolated terpenes were in the agave, we created our own proprietary process before and during distillation, which helped us maintain those terpenes without adding or subtracting the natural elements in the agave.

Everything is pre-distillation.

The terpene aromatics are already in the agave and we are just shifting the isolated terpenes slightly in pursuit of the benefits. Because everything is in our distillation process, any aromatic shift is subtle and part of the experience of our tequila.

Who Are These People

Dr. Robert Summers is a co-founder of El Sativo Tequila as well as Nevada Botanical Science (NBS). Established in 2014 by a group of physicians and healthcare providers, NBS is a wellness-driven, science-based company that believes in the promise of medical cannabis and is working to develop its potential for the benefit of the community. Their mission is to develop pure, safe, effective medical cannabis to enhance health and quality of life for their patients and community. They strongly believe in the importance of the role of the physician in determining medicinal quality and dosing. NBS is actively cultivating cannabis, researching strain effectiveness, and modifying composition to develop effective products that address a variety of conditions, diseases, and ailments.

What I Learned

1. All this functional stuff? Oh, I don't know. Add salt to vodka and claim it as an electrolyte beverage, right? I'm wary. 
2. This product is mostly talking about mood-elevating and energy lifting properties (which fair to say is a property of alcohol in general at least for the first couple of drinks), and anti-inflammatory properties- but I don't know enough about that part to say.  
3. The terpene extraction process apparently doesn't impact flavor much - this was actually my main question - did it win Best Tequila in the SFWSC because of this process? Seems like they're saying no, it just tastes good. 

So Many Questions

1. Is the extraction process on the same batch of agave that makes the batch tequila, or is it a separate process that is then added, pre-distillation, to a batch of tequila? In other words, is it part of the tequila-making process or a tequila-based additive? 
2. The terpenes are extracted at some point and added back pre-distillation to the batch if I'm reading this correctly. Is the "distillation" mentioned in the terpene extraction a separate process from the distillation of fermented agave? 
3. My guess is that terpenes are extracted through the CO2/pressure process from raw agave. And since the brand mentions a traditional baking process and no autoclaves but doesn't mention distillation, that their proprietary distillation process is column distillation and they're pulling off some spirit at a particular plate on the still that will contain the desired terpenes. But just a guess. 

The brand representatives were helpful but not willing to go into further detail about their proprietary production process, which is understandable. 

So if you've read this far, thanks for following along in my journey to understands terpenes in general and as applied to tequila specifically.

Many of my readers know far more chemistry than I do so if you're one of them and have something to add, by all means please do!