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Controlling Terpenes and
Cannabinoids in Flower and
Extract
Cannabis Curing & Extraction Research
by
Dr. Markus Roggen
Complex Biotech Discovery Ventures
Agenda
• Introduction
• Data Visualization
• Different Strains = Different Chemovars
• Drying & Storage
• Drying Conditions
• Gasses for Storage
• Extraction
• Particle Size
• DoE
• Post-Processing
• Decarboxylation
Cannabis Processing Pipeline
• Drying and curing
• Extraction
• Post processing
CBDA
CBD THCA
THC
Cannabis Processing Pipeline
• Drying and curing
• Extraction
• Post processing
Myrcene
a-Pinene
b-Pinene
Limonene
b-Caryophyllene
Cannabis Flower and Medicine
• Cannabinoid ratios and concentrations show little variability
• Terpene ratios and concentrations show strong variability
Cannabinoid Chemotaxonomy: DOI:10.1038/s41598-018-31120-2
Terpene Chemovars: DOI: 10.1089/can.2016.0040
Gorilla Glue Sour Diesel
Cookies
Sour Tangie
Lemonade Haze
What is in the Plant
6
>140 Cannabinoids
>200 Terpenes
~30 Flavonoids
Alcohols, Phenols
Aldehydes, Ketones
Alkaloids
Carbohydrates, Fatty Acids
Lactones
Drying and Curing
• Drying room conditions influence on terpenes
30%
Drying
Conditions
Slower
Faster
Air
Vacuum
N2
Ar
Long Term
Storage
20%
CO2
Storage
Atmosphere
Water Activity during Dry and Cure
0.45
0.55
0.65
0.75
0.85
0.95
0 5 10 15 20 25 30
WaterActivity
Day
Water Activity
Aw of 0.65 represents the value in which
Botrytis cannot continue to grow
Terpene Content (% dry weight)
Rapid Dry Slow Dry
Lemonade Haze 1.42 1.82
Sour Tangie 1.69 2.2
• Moisture loss is driven by a difference in vapor pressure
• Balance between inhibiting mold growth and terpene loss
Drying and Curing
• Drying room conditions influence on terpenes
• Storage time influences on cannabinoids
• Drying room conditions influence on terpenes
• Storage time influences on cannabinoids
• Curing Gases influence on terpene ratios
30%
Drying
Conditions
Slower
Faster
Air
Vacuum
N2
Ar
Long Term
Storage
20%
CO2
Storage
Atmosphere
Drying and Curing
• Drying room conditions influence on terpenes
• Storage time influences on cannabinoids
• Curing Gases influence on terpene ratios
30%
Drying
Conditions
Slower
Faster
Air
Vacuum
N2
Ar
Long Term
Storage
20%
CO2
Storage
Atmosphere
Storing under Modified Atmosphere
18.00
20.00
22.00
24.00
26.00
28.00
30.00
0 2 4 6 8 10 12 14 16
w%
Weeks
Cannabinoids
Air Vacuum N2 Ar CO2
0
0.5
1
1.5
2
2.5
0 2 4 6 8 10 12 14 16 18
w%
Weeks
Total Terpens
Air Vacuum N2 Ar CO2
Extraction
• Particle size effects yield and precision
2mm
Milling
Method
Whole
Flower
Food
Blender
Extraction
Method
Terpenes
THC
THCA
CBDA
Extraction
• Particle size effects yield and precision
2mm
Terpenes
THC
THCA
CBDA
Whole
Flower
Food
Blender
Milling Method
Effect of Milling
Does milling destroy THC?
0%
1%
2%
%decarb by Size
0
0.2
0.4
0.6
0.8
1
1.2
1.4
%wt. Terpenes by Size
Effect of Milling
But it does give you higher yields!
20
22
24
26
28
30
32
34
Non-Ground Food Blender 2 mm 6 mm 10 mm
%Recovery
Cannabinoid Recovery by Size
75
80
85
90
95
Non-Ground Food Blender 2 mm 6 mm 10 mm
%Recovery
Terpene Recovery by Size
Extraction Parameters
• 3 kg of plant matter
• Terpene Fraction (F1): 1100 psi, 34˚C, 5 h
• Cannabinoid Fraction (F2): 1900 psi, 60˚C, 12 h
Extraction Precision Terpenes
30
35
40
45
50
55
Non-Ground Food Blender 2 mm 6 mm 10 mm
%conc.
Terpene Concentration F1
Higher is better, Food Blender wins
0
1
2
3
4
5
Non-Ground Food Blender 2 mm 6 mm 10 mm
%conc.
Terpene Concentration F2
Lower is better, 2mm wins
• 3 kg of plant matter
• Terpene Fraction (F1): 1100 psi, 34˚C, 5 h
• Cannabinoid Fraction (F2): 1900 psi, 60˚C, 12 h
0
2
4
6
Non-Ground Food Blender 2 mm 6 mm 10 mm
%conc.
Cannabinoid Concentration F1
Lower is better, 10mm wins
55
60
65
70
75
Non-Ground Food Blender 2 mm 6 mm 10 mm
%conc.
Cannabinoid Concentration F2
Higher is better, 2mm wins
Extraction Precision Cannabinoids
• 3 kg of plant matter
• Terpene Fraction (F1): 1100 psi, 34˚C, 5 h
• Cannabinoid Fraction (F2): 1900 psi, 60˚C, 12 h
Extraction
• Particle size effects yield and precision
• SFE can extract terpene fractions
• SFE can extract either THCA or THC
2mm
Whole
Flower
Food
Blender
Terpenes
THC
THCA
Milling Method
Extraction Method
Extraction
• Particle size effects yield and precision
• SFE can extract terpene fractions
• SFE can extract either THCA or THC
• SFE can change the THC to CBD ratio
2mm
Milling Method
Extraction Method
Terpenes
THC
THCA
CBDA
Whole
Flower
Food
Blender
Analyzing CO2 SFE for THC Recovery (Super)
• a= 14.9 xT + 123 xp + 18.4 xTxp
Analyzing CO2 SFE for THC Recovery (Sub)
• a= - 7.75 xT + 126 xp + 59.3 xTxp
Analyzing CO2 SFE for %Terpene (Super)
• a= - 14.9 xT - 11.7 xp + 16.8 xTxp
Analyzing CO2 SFE for %Terpene (Sub)
• a= 11.8 xT - 16.6 xp - 12.5 xTxp
Comparing Sub- and Supercritical
• SFE, 900.0 – 1900 psi, 5.0 – 60 ˚C, 22h max
Response Sub Super
THC Recovery 60% 80%
Terpene Fraction 52% at 34% yield 63% at 82% yield
Lessons learned in SFE
• THC extracts faster than THCA
• THC to THCA ratio adjusted by SFE
% Decarboxylation S.M. 7h 22h
Exp. B 8.0% 25% 10%
Exp. J 14% 25% 14%
Lessons learned in SFE
• CBD extracts faster than THC
• CBD to THC ratio adjusted by SFE
CBD/THC S.M. 7h 22h
Exp. A 4.1E-03 1.3E-02 5.0E-03
Exp. J 1.7E-04 1.3E-03 3.1E-03
Bonus: Decarboxylation of CBDA
slower than for THCA
J. of Supercritical Fluids, 2010, 603
Lessons learned in SFE
• Enrichment in minor cannabinoids
• CBG enrichment by SFE
CBG/total Canna. S.M. 7h 22h
Exp. B 2.9% 6.% 2.9%
Exp. J 3.0% 13% 4.9%
J. of Supercritical Fluids, 2010, 603
Lessons learned in SFE
• Changing terpene profiles in SFE
• Sativa: rich in monoterpenes
• Indica: rich in sesquiterpenes
Hazekamp, et al.; Cannabis and Cannabinoid Research 2016, 202
Visual Guide to Extracts
30
Post-Processing
• Decarboxylation under CO2 vs air
Air
CO2
Decarboxylation
Method
Distillation
Method
IR monitoring of decarboxylation
IR as quick and cheap method to monitor decarboxylation
IR monitoring of decarboxylation
IR as quick and cheap method to monitor decarboxylation
-10
0
10
20
30
40
50
60
0 10 20 30 40 50 60 70 80 90
Concentration(%)
Elapsed Time (Minutes)
Reference THC Predicted THC Reference THCA Predicted THCA
15
25
35
45
55
65
75
85
15 35 55 75
PredictedTHC(%)
Reference THC (%)
THC
-5
0
5
10
15
20
25
30
35
40
0 10 20 30 40
PredictedTHCA(%)
Reference THCA (%)
THCA
Post-Processing
• Decarboxylation under CO2 vs air
• Distillation to purify THC
Air
CO2
Decarboxylation
Method
Distillation
Method
Final Product: The Blind Side
• Patient: Male, mid-30, 8 seizures per day
• CBD/THC 3:1 tincture, 40 mg/mL, no terpenes, MCT oil:
• seizure-free for 9 weeks
• Next batch of 3:1 oil:
• seizures re-start immediately
• THC came from two different cultivars: Diamond OG and Lemonade Haze
CBD THC THCA CBDA CBN CBG THCV CBGA CBC
Diamond OG 300 100 15.3 0.00 0.66 1.76 0.73 0.99 0.00
Lemonade Haze 300 100 15.6 0.00 0.45 1.62 1.19 0.00 1.06
Research Collaborations
cbdvl.com
slideshare.net/MarkusRoggen email: markus@cbdvl.com
Complex Biotech Discovery Ventures

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LabRoots 2019: Molecular Manipulation

  • 1. Controlling Terpenes and Cannabinoids in Flower and Extract Cannabis Curing & Extraction Research by Dr. Markus Roggen Complex Biotech Discovery Ventures
  • 2. Agenda • Introduction • Data Visualization • Different Strains = Different Chemovars • Drying & Storage • Drying Conditions • Gasses for Storage • Extraction • Particle Size • DoE • Post-Processing • Decarboxylation
  • 3. Cannabis Processing Pipeline • Drying and curing • Extraction • Post processing CBDA CBD THCA THC
  • 4. Cannabis Processing Pipeline • Drying and curing • Extraction • Post processing Myrcene a-Pinene b-Pinene Limonene b-Caryophyllene
  • 5. Cannabis Flower and Medicine • Cannabinoid ratios and concentrations show little variability • Terpene ratios and concentrations show strong variability Cannabinoid Chemotaxonomy: DOI:10.1038/s41598-018-31120-2 Terpene Chemovars: DOI: 10.1089/can.2016.0040 Gorilla Glue Sour Diesel Cookies Sour Tangie Lemonade Haze
  • 6. What is in the Plant 6 >140 Cannabinoids >200 Terpenes ~30 Flavonoids Alcohols, Phenols Aldehydes, Ketones Alkaloids Carbohydrates, Fatty Acids Lactones
  • 7. Drying and Curing • Drying room conditions influence on terpenes 30% Drying Conditions Slower Faster Air Vacuum N2 Ar Long Term Storage 20% CO2 Storage Atmosphere
  • 8. Water Activity during Dry and Cure 0.45 0.55 0.65 0.75 0.85 0.95 0 5 10 15 20 25 30 WaterActivity Day Water Activity Aw of 0.65 represents the value in which Botrytis cannot continue to grow Terpene Content (% dry weight) Rapid Dry Slow Dry Lemonade Haze 1.42 1.82 Sour Tangie 1.69 2.2 • Moisture loss is driven by a difference in vapor pressure • Balance between inhibiting mold growth and terpene loss
  • 9. Drying and Curing • Drying room conditions influence on terpenes • Storage time influences on cannabinoids • Drying room conditions influence on terpenes • Storage time influences on cannabinoids • Curing Gases influence on terpene ratios 30% Drying Conditions Slower Faster Air Vacuum N2 Ar Long Term Storage 20% CO2 Storage Atmosphere
  • 10. Drying and Curing • Drying room conditions influence on terpenes • Storage time influences on cannabinoids • Curing Gases influence on terpene ratios 30% Drying Conditions Slower Faster Air Vacuum N2 Ar Long Term Storage 20% CO2 Storage Atmosphere
  • 11. Storing under Modified Atmosphere 18.00 20.00 22.00 24.00 26.00 28.00 30.00 0 2 4 6 8 10 12 14 16 w% Weeks Cannabinoids Air Vacuum N2 Ar CO2 0 0.5 1 1.5 2 2.5 0 2 4 6 8 10 12 14 16 18 w% Weeks Total Terpens Air Vacuum N2 Ar CO2
  • 12. Extraction • Particle size effects yield and precision 2mm Milling Method Whole Flower Food Blender Extraction Method Terpenes THC THCA CBDA
  • 13. Extraction • Particle size effects yield and precision 2mm Terpenes THC THCA CBDA Whole Flower Food Blender Milling Method
  • 14. Effect of Milling Does milling destroy THC? 0% 1% 2% %decarb by Size 0 0.2 0.4 0.6 0.8 1 1.2 1.4 %wt. Terpenes by Size
  • 15. Effect of Milling But it does give you higher yields! 20 22 24 26 28 30 32 34 Non-Ground Food Blender 2 mm 6 mm 10 mm %Recovery Cannabinoid Recovery by Size 75 80 85 90 95 Non-Ground Food Blender 2 mm 6 mm 10 mm %Recovery Terpene Recovery by Size
  • 16. Extraction Parameters • 3 kg of plant matter • Terpene Fraction (F1): 1100 psi, 34˚C, 5 h • Cannabinoid Fraction (F2): 1900 psi, 60˚C, 12 h
  • 17. Extraction Precision Terpenes 30 35 40 45 50 55 Non-Ground Food Blender 2 mm 6 mm 10 mm %conc. Terpene Concentration F1 Higher is better, Food Blender wins 0 1 2 3 4 5 Non-Ground Food Blender 2 mm 6 mm 10 mm %conc. Terpene Concentration F2 Lower is better, 2mm wins • 3 kg of plant matter • Terpene Fraction (F1): 1100 psi, 34˚C, 5 h • Cannabinoid Fraction (F2): 1900 psi, 60˚C, 12 h
  • 18. 0 2 4 6 Non-Ground Food Blender 2 mm 6 mm 10 mm %conc. Cannabinoid Concentration F1 Lower is better, 10mm wins 55 60 65 70 75 Non-Ground Food Blender 2 mm 6 mm 10 mm %conc. Cannabinoid Concentration F2 Higher is better, 2mm wins Extraction Precision Cannabinoids • 3 kg of plant matter • Terpene Fraction (F1): 1100 psi, 34˚C, 5 h • Cannabinoid Fraction (F2): 1900 psi, 60˚C, 12 h
  • 19. Extraction • Particle size effects yield and precision • SFE can extract terpene fractions • SFE can extract either THCA or THC 2mm Whole Flower Food Blender Terpenes THC THCA Milling Method Extraction Method
  • 20. Extraction • Particle size effects yield and precision • SFE can extract terpene fractions • SFE can extract either THCA or THC • SFE can change the THC to CBD ratio 2mm Milling Method Extraction Method Terpenes THC THCA CBDA Whole Flower Food Blender
  • 21. Analyzing CO2 SFE for THC Recovery (Super) • a= 14.9 xT + 123 xp + 18.4 xTxp
  • 22. Analyzing CO2 SFE for THC Recovery (Sub) • a= - 7.75 xT + 126 xp + 59.3 xTxp
  • 23. Analyzing CO2 SFE for %Terpene (Super) • a= - 14.9 xT - 11.7 xp + 16.8 xTxp
  • 24. Analyzing CO2 SFE for %Terpene (Sub) • a= 11.8 xT - 16.6 xp - 12.5 xTxp
  • 25. Comparing Sub- and Supercritical • SFE, 900.0 – 1900 psi, 5.0 – 60 ˚C, 22h max Response Sub Super THC Recovery 60% 80% Terpene Fraction 52% at 34% yield 63% at 82% yield
  • 26. Lessons learned in SFE • THC extracts faster than THCA • THC to THCA ratio adjusted by SFE % Decarboxylation S.M. 7h 22h Exp. B 8.0% 25% 10% Exp. J 14% 25% 14%
  • 27. Lessons learned in SFE • CBD extracts faster than THC • CBD to THC ratio adjusted by SFE CBD/THC S.M. 7h 22h Exp. A 4.1E-03 1.3E-02 5.0E-03 Exp. J 1.7E-04 1.3E-03 3.1E-03 Bonus: Decarboxylation of CBDA slower than for THCA J. of Supercritical Fluids, 2010, 603
  • 28. Lessons learned in SFE • Enrichment in minor cannabinoids • CBG enrichment by SFE CBG/total Canna. S.M. 7h 22h Exp. B 2.9% 6.% 2.9% Exp. J 3.0% 13% 4.9% J. of Supercritical Fluids, 2010, 603
  • 29. Lessons learned in SFE • Changing terpene profiles in SFE • Sativa: rich in monoterpenes • Indica: rich in sesquiterpenes Hazekamp, et al.; Cannabis and Cannabinoid Research 2016, 202
  • 30. Visual Guide to Extracts 30
  • 31. Post-Processing • Decarboxylation under CO2 vs air Air CO2 Decarboxylation Method Distillation Method
  • 32. IR monitoring of decarboxylation IR as quick and cheap method to monitor decarboxylation
  • 33. IR monitoring of decarboxylation IR as quick and cheap method to monitor decarboxylation -10 0 10 20 30 40 50 60 0 10 20 30 40 50 60 70 80 90 Concentration(%) Elapsed Time (Minutes) Reference THC Predicted THC Reference THCA Predicted THCA 15 25 35 45 55 65 75 85 15 35 55 75 PredictedTHC(%) Reference THC (%) THC -5 0 5 10 15 20 25 30 35 40 0 10 20 30 40 PredictedTHCA(%) Reference THCA (%) THCA
  • 34. Post-Processing • Decarboxylation under CO2 vs air • Distillation to purify THC Air CO2 Decarboxylation Method Distillation Method
  • 35. Final Product: The Blind Side • Patient: Male, mid-30, 8 seizures per day • CBD/THC 3:1 tincture, 40 mg/mL, no terpenes, MCT oil: • seizure-free for 9 weeks • Next batch of 3:1 oil: • seizures re-start immediately • THC came from two different cultivars: Diamond OG and Lemonade Haze CBD THC THCA CBDA CBN CBG THCV CBGA CBC Diamond OG 300 100 15.3 0.00 0.66 1.76 0.73 0.99 0.00 Lemonade Haze 300 100 15.6 0.00 0.45 1.62 1.19 0.00 1.06
  • 36. Research Collaborations cbdvl.com slideshare.net/MarkusRoggen email: markus@cbdvl.com Complex Biotech Discovery Ventures

Editor's Notes

  1. Even more important then total yield is extraction precision. Therefore we do two fractions and assess “Trennschärfe”
  2. Non-Ground is so horrible.
  3. Non-Ground is really bad. And 2mm is great.