- DELIC Labs conducts research on cannabis and mushroom production, collaborating with academic and industry partners. Research topics include process optimization, analytics, and formulation studies. - CBD usage is increasing globally but users face confusion over legality, regulation, and determining proper dosages. CBD concentrations in e-liquids were found to deviate significantly from labeled amounts in some cases. - CBD is subject to degradation over time from factors like heat, light, pH levels, and metal leaching. On average, 20% degradation was observed after 30 days at 37°C.

1. Purple Rain: Discolouration
Results from Cascading Photo-
Redox Reactions
Brodie Thomson, Dr. Markus Roggen

2. Introduction
DELIC Labs is a research venture that seeks to add fundamental scientific
insight to the field of cannabis and mushroom production.
We seek to support the cannabis and mushroom industries by
establishing a centralized hub in Vancouver, BC, for collaborative
research focused on:
• Process Design
• Process Optimization
• Process Analytics
• Formulation Research

3. Collaborative Research
DELIC Labs collaborates with academic, industry and private groups
around the globe. Some highlights of those collaborations are:
• University of British Columbia, Vancouver
• Loyalist College, Belleville
• Via Innovations by Dr. Monica Vialpando
• Verdient Science by Dr. Linda Klumpers
Fundamental Collaboration

4. Research Topics
• Chemometrics and data analytics for process control and optimization
• Kinetic studies to understand mechanisms
• In-process analytics for process control
• Computational studies to understand mechanisms
• Process development, like crystallization
Fundamental Cannabis and Mushroom Chemistry

5. 1
Outline
- Degradation routes of CBD

6. 1
Outline
- Degradation routes of CBD
- Previous work: the search for HU-331’s anion

7. 1
Outline
- Degradation routes of CBD
- Previous work: the search for HU-331’s anion
- Origin of orange and purple colours in CBD-containing
solutions

8. CBD Usage
[1] Dobian, CBD Market to reach $19.5 billion by 2025, but only with FDA approval says top researcher. Forbes. July
28, 2021. Available at https://www.forbes.com/sites/irisdorbian/?sh=2cd295c94bf8.
2
- Global CBD sales predicted to exceed
US $19 billion by 2025.1

9. CBD Usage
[1] Dobian, CBD Market to reach $19.5 billion by 2025, but only with FDA approval says top researcher. Forbes. July
28, 2021. Available at https://www.forbes.com/sites/irisdorbian/?sh=2cd295c94bf8.
[2] Wheeler, M.; Williams Merten, J.; Gordon, B. T.; Hamadi, H. Substance Use & Misuse, 2020, 55, 1138-1145.
2
- Global CBD sales predicted to exceed
US $19 billion by 2025.1
- Users of CBD (including E-liquids) are
confused of both the current legality and
regulation.2

10. CBD Usage
[1] Dobian, CBD Market to reach $19.5 billion by 2025, but only with FDA approval says top researcher. Forbes. July
28, 2021. Available at https://www.forbes.com/sites/irisdorbian/?sh=2cd295c94bf8.
[2] Wheeler, M.; Williams Merten, J.; Gordon, B. T.; Hamadi, H. Substance Use & Misuse, 2020, 55, 1138-1145.
2
- Global CBD sales predicted to exceed
US $19 billion by 2025.1
- Users of CBD (including E-liquids) are
confused of both the current legality and
regulation.2
- Large number of CBD users report no
framework for determining dosage.2

11. CBD Usage
[1] Dobian, CBD Market to reach $19.5 billion by 2025, but only with FDA approval says top researcher. Forbes. July
28, 2021. Available at https://www.forbes.com/sites/irisdorbian/?sh=2cd295c94bf8.
[2] Wheeler, M.; Williams Merten, J.; Gordon, B. T.; Hamadi, H. Substance Use & Misuse, 2020, 55, 1138-1145.
[3] Mazzetti, C.; Ferri, E.; Pozzi, M.; Labra, M. Sci. Rep. 2020, 10, 3697. 2
- Global CBD sales predicted to exceed
US $19 billion by 2025.1
- Users of CBD (including E-liquids) are
confused of both the current legality and
regulation.2
- Large number of CBD users report no
framework for determining dosage.2
- Of 13 e-liquids tested, 38% of samples
were labelled within 10% of reported CBD
concentration.3

12. CBD Usage
[1] Dobian, CBD Market to reach $19.5 billion by 2025, but only with FDA approval says top researcher. Forbes. July
28, 2021. Available at https://www.forbes.com/sites/irisdorbian/?sh=2cd295c94bf8.
[2] Wheeler, M.; Williams Merten, J.; Gordon, B. T.; Hamadi, H. Substance Use & Misuse, 2020, 55, 1138-1145.
[3] Mazzetti, C.; Ferri, E.; Pozzi, M.; Labra, M. Sci. Rep. 2020, 10, 3697. 2
-100
-80
-60
-40
-20
0
20
Deviation
(%)
Sample Tested
Deviation from advertised CBD content
- Global CBD sales predicted to exceed
US $19 billion by 2025.1
- Users of CBD (including E-liquids) are
confused of both the current legality and
regulation.2
- Large number of CBD users report no
framework for determining dosage.2
- Of 13 e-liquids tested, 38% of samples
were labelled within 10% of reported CBD
concentration.3

13. CBD Content Degradation
3

14. CBD Content Degradation
- Average CBD degradation of 20%
30 days at 37°C.3
[3] Mazzetti, C.; Ferri, E.; Pozzi, M.; Labra, M. Sci. Rep. 2020, 10, 3697.
3
Heat

15. CBD Content Degradation
- Average CBD degradation of 20%
30 days at 37°C.3
- Effect of light alone resulted in 15%
CBD degradation in 30 days.3
[3] Mazzetti, C.; Ferri, E.; Pozzi, M.; Labra, M. Sci. Rep. 2020, 10, 3697.
3
Light
Heat

16. CBD Content Degradation
- Average CBD degradation of 20%
30 days at 37°C.3
- Effect of light alone resulted in 15%
CBD degradation in 30 days.3
- Optimum CBD storage between pH
4-6.4
3
Light
Heat
Bronsted Acid
[3] Mazzetti, C.; Ferri, E.; Pozzi, M.; Labra, M. Sci. Rep. 2020, 10, 3697.
[4] Jaidee, W.; Siridechakorn, I.; Nessopa, S.; Wisuitiprot, V.; Chaiwangrach, N.; Ingkaninan, K.;
Waranuch, N. Cannabis Cannabinoid Res. 2022, 7, 537-547.

17. CBD Content Degradation
- Average CBD degradation of 20%
30 days at 37°C.3
- Effect of light alone resulted in 15%
CBD degradation in 30 days.3
- Optimum CBD storage between pH
4-6.4
- Metal leaching – LA formation
3
Light
Heat
Bronsted Acid
[3] Mazzetti, C.; Ferri, E.; Pozzi, M.; Labra, M. Sci. Rep. 2020, 10, 3697.
[4] Jaidee, W.; Siridechakorn, I.; Nessopa, S.; Wisuitiprot, V.; Chaiwangrach, N.; Ingkaninan, K.;
Waranuch, N. Cannabis Cannabinoid Res. 2022, 7, 537-547.
Lewis Acid

18. CBD Content Degradation
- Average CBD degradation of 20%
30 days at 37°C.3
- Effect of light alone resulted in 15%
CBD degradation in 30 days.3
- Optimum CBD storage between pH
4-6.4
- Metal leaching – LA formation
3
Light
Heat
Bronsted Acid
[3] Mazzetti, C.; Ferri, E.; Pozzi, M.; Labra, M. Sci. Rep. 2020, 10, 3697.
[4] Jaidee, W.; Siridechakorn, I.; Nessopa, S.; Wisuitiprot, V.; Chaiwangrach, N.; Ingkaninan, K.;
Waranuch, N. Cannabis Cannabinoid Res. 2022, 7, 537-547.
Lewis Acid

19. CBD Degradation
- Anecdotal evidence supports the
degradation of CBD solution with multiple
reports of CBD e-liquids and solutions
turning purple.
[5] Reddit. CBD E-juice turned purple in the
tankhttps://www.reddit.com/r/Vaping/comments/e0z2ru/cbd_ejuice_turned_purple_in_the_tank/
(Accessed March, 2022).
Sourced from Reddit5
4

20. The Beam Test
- A classical colourimetric test for the identification of hashish using ethanolic KOH (5%).6
[6] Beam, W. Chemistry section in Fourth Report of Wellcome Tropical Research Laboratories, part B.
Khartoum, 1911; pp 25.
5

21. The Beam Test
- A classical colourimetric test for the identification of hashish using ethanolic KOH (5%).6
Cannabinoids
responsible for a
positive test
result7,8
[6] Beam, W. Chemistry section in Fourth Report of Wellcome Tropical Research Laboratories, part B.
Khartoum, 1911; pp 25.
[7] Adams, R. Marijuana. Harvey Lecture. Bull. N. Y. Acad. Med. 1942, 18 (11), 705-730.
[8] Mechoulam, R.; Ben-Zvi, Z.; Gaoni, Y. Hashish-XIII. On the nature of the beam test. Tetrahedron, 1968,
5615-5624.
5

22. Tracking HU-331 Concentration
𝒉𝒗
(65% PG, 30% VG, 5%
CBD)
Mass Chromatogram
6

23. R² = 0.9933
0.4
0.5
0.6
0.7
0.8
0.9
1
1.1
0 10 20 30 40 50 60
HU-331
Degradation
Relative
to
T
0
Time (min)
Light
Dark
Storage
Conditions
HU-331 Rate of Decomposition
45% reduction in [HU-331] after 60
minutes exposure to white light
- Is HU-331 degradation a light-driven process?
HU-331 (0.23 mg) +
dinitrobenzene
internal standard in
DMSO-d6 (0.5 mL)
7

24. 0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1
380 430 480 530 580 630 680
Absorbance
(A)
Wavelength (nm)
CBD
HU-331 and CBD at 0.5 mg mL-1 in IPA. Λmax of HU-331, 413 nm.
448 nm light emission
Complete degradation of HU-331 in under 15
minutes
Role of HU-331 vs CBD
8

25. 448 nm light emission
HU-331 responsible for the
colouration?
48 h
Role of HU-331 vs CBD
9

26. Presence of HU-331 anion?
48 h
10
No HU-331 anion at high
concentration (>10 mg HU-331)

27. Presence of HU-331 anion?
48 h
11
No HU-331 anion at high concentration
(>10 mg HU-331) – what is purple?

28. Computational Exploration of Absorption
12
- TD-DFT-calculated visible light
absorption spectra for HU-331 and
its anion.

29. Computational Exploration of Absorption
12
- TD-DFT-calculated visible light
absorption spectra for HU-331 and
its anion.
- Experimental data (linear) and
calculated data (bar) closely
correspond upon deprotonation of
the hydroxyquinone.

30. 13
Computational Exploration of Absorption
𝝅𝑻
𝒏𝑶𝟒



40%
15%
35%
𝝅𝑯𝑩𝒒𝟒
Energy
HU-331
𝝅𝑯𝑩𝒒𝟑

31. 14
Computational Exploration of Absorption
𝝅𝑻
𝒏𝑶𝟒



40%
15%
35%
𝝅𝑯𝑩𝒒𝟑
𝝅𝑯𝑩𝒒𝟒
H+



𝝅𝑻
𝝅𝑯𝑩𝒒𝟑
95%
< 5%
𝝅𝑯𝑩𝒒𝟒
𝒏𝑶𝟐
Energy
HU-331 HU-331

32. 15
Computational Exploration of Absorption
𝝅𝑻
𝒏𝑶𝟒



40%
15%
35%
𝝅𝑯𝑩𝒒𝟒
Energy
HU-331
- How would absorption calculations
change when the structure of HU-331
is altered?
Olivetol-HQ
𝝅𝑯𝑩𝒒𝟑

33. 16
∆𝐸~400𝑐𝑚−1
∆𝐸~3000𝑐𝑚−1
HU-331
3
11
Olivetol-HQ
Computational Exploration of Absorption
𝝅𝑻
𝒏𝑶𝟒



40%
15%
35%
𝝅𝑯𝑩𝒒𝟒
Energy
HU-331
𝝅𝑯𝑩𝒒𝟑

34. 17
Computational Exploration of Absorption
HU-331
anion
𝝅𝑻
𝒏𝑶𝟒



40%
15%
35%
𝝅𝑯𝑩𝒒𝟑
𝝅𝑯𝑩𝒒𝟒
H+



𝝅𝑻
𝝅𝑯𝑩𝒒𝟑
95%
< 5%
𝝅𝑯𝑩𝒒𝟒
𝒏𝑶𝟐
Energy
HU-331 HU-331
Olivetol-HQ
anion

35. 17
Computational Exploration of Absorption
HU-331
anion
𝝅𝑻
𝒏𝑶𝟒



40%
15%
35%
𝝅𝑯𝑩𝒒𝟑
𝝅𝑯𝑩𝒒𝟒
H+



𝝅𝑻
𝝅𝑯𝑩𝒒𝟑
95%
< 5%
𝝅𝑯𝑩𝒒𝟒
𝒏𝑶𝟐
Energy
HU-331 HU-331
Olivetol-HQ
anion
Structure of terpene is irrelevant

36. 18
Comparison to Experimental Data
HU-331
anion
Olivetol-HQ
anion

37. 18
Comparison to Experimental Data
HU-331
anion
0
0.1
0.2
0.3
0.4
0.5
0.6
380 480 580 680
Absorbance
(A)
Wavenlength (nm)
HU-331 Anion
Olivetol
Hydroxyquinone
Anion
Olivetol-HQ
anion
520 nm
540 nm

38. Conclusions
- Likely that most olivetol-based structures which can from the hydroxyquinone will result in
a purple colour.
Cannabinoids
responsible for a
positive test result5
[6] Beam, W. Chemistry section in Fourth Report of Wellcome Tropical Research Laboratories, part B.
Khartoum, 1911; pp 25.
[7] Adams, R. Marijuana. Harvey Lecture. Bull. N. Y. Acad. Med. 1942, 18 (11), 705-730.
[8] Mechoulam, R.; Ben-Zvi, Z.; Gaoni, Y. Hashish-XIII. On the nature of the beam test. Tetrahedron, 1968,
5615-5624.
19

39. Conclusions
- Likely that most olivetol-based structures which can from the hydroxyquinone will result in
a purple colour.
Example
quinones
responsible for
the purple
colouration6
Cannabinoids
responsible for a
positive test result5
[6] Beam, W. Chemistry section in Fourth Report of Wellcome Tropical Research Laboratories, part B.
Khartoum, 1911; pp 25.
[7] Adams, R. Marijuana. Harvey Lecture. Bull. N. Y. Acad. Med. 1942, 18 (11), 705-730.
[8] Mechoulam, R.; Ben-Zvi, Z.; Gaoni, Y. Hashish-XIII. On the nature of the beam test. Tetrahedron, 1968,
5615-5624.
19

40. Conclusions: Tracking HU-331 Concentration
𝒉𝒗
(65% PG, 30% VG, 5%
CBD)
Mass Chromatogram
20

41. University of British Columbia:
Prof Glenn Sammis – Supervisor
Prof Tao Huan
Prof Pierre Kennepohl
Dr Maria Ezhova
Acknowledgements
DELIC Labs:
Kendra Payne
Sajni Shah
Dr Eric Janusson
Dr Tom Dupree
Amanda Assen
Dingding Xuan
Ali Wasti
20

42. Thank you! Questions?