. 2023 Sep 25;21(12):2424–2430. doi: 10.2174/1570159X21666230623104624

Table 1.

Analytical methods for diastereomers of HHC and other related cannabinoids determination in non-biological matrices.

Sample	Analytes	Sample Preparation	Instrument	Ionization Source	Column	Mobile Phase	Run Time (min)	References
e-cigarette liquids	HHC, ∆⁸-THC, ∆^6a, ^10a-THC, THC-P, THC-O	Dilute and shoot	HPLC-MS/MS	ESI+	Phenomenex Kinetex^® 2.6 μm C18 (100Å 150 x 3 mm)	Isocratic H₂O:ACN (25:75 v/v) + 1 mg/mL ammonium formate + 1% formic acid	-	[41]
e-cigarette liquids	HHC, ∆⁸-THC, ∆⁹-THC, ∆^6a,^10a-THC, THC-O, THC-P, CBD-di-O	Dilute and shoot	GC-MS	EI	HP-5MS column (30 m, 0.25 mm id, 0.25 μm)	Helium	26.33	[42]
e-cigarette liquids	HHC, ∆⁸-THC, ∆⁹-THC, ∆^6a,^10a-THC, THC-O, THC-P, CBD-di-O	Dilute and shoot	DART TOF-MS	ESI+	-	Helium	-	[42]
Pure standards	9(S)-HHC, 9(R)-HHC, (-)-trans-Δ⁸-THC, (-)-trans-Δ⁹-THC, 9α-OH-HHC, 9β-OH-HHC, ∆^6a,^10a-THC, CBN, CBD	Dilute and shoot	GC-MS	EI	30 m capillary 35% diphenyl/65% dimethylpolysi-loxane bonded-phase)	Helium	-	[43]
Pure standards		Dilute and shoot	HPLC-PDA	-	150 mm x 4.6 mm 2.7 mm particles (Raptor ARC-18, Cat # 9314A65)	5 mM ammonium formate + 0.1% formic acid (25%) + acetonitrile + 0.1% formic acid (75%)	-	[43]
Pure standards	9(S)-HHC, 9(R)-HHC	-	GC-MS	EI	Restek Rtx-5 MS column	Helium	25-minute	[44]
Pure standards	9(S)-HHC, 9(R)-HHC	-	HPLC-UV	-	Gemini-C18 250 x 4.6 mm, 5 μm	20:80:0.1 Water/Methanol/ acetic acid	-	[44]
Crude extract	9(S)-HHC, 9(R)-HHC	Preparative SFC	SFC	-	Column 4.6 x 100 mm Chiralpak AD-H from Chiral Technologies (West Chester, PA)	Isocratic elution CO₂, Co-solvent Isopropanol	-	[46]
Hemp derived resin	9(S)-HHC, 9(R)-HHC	Extraction with hexane and derivatization with MSTFA	GC-MS	EI	Agilent capillary column CP sil 8 CB (15 m · 0.25 mm i.d., 0.25 µm film thickness)	Helium	13	[45]
Hemp derived resin	9(S)-HHC, 9(R)-HHC	-	LC-QTrap	-	Acquity fluoro-phenyl column (130Å, 1.7 µm, 2.1x 100 mm) (waters)	Isocratic elution 0.1% formic acid in H₂O: 0.1% formic acid in CAN (35:65 v/v)	-	[45]

Abbreviations: ACN, acetonitrile; CBD, cannabidiol; CBD-di-O, cannabidiol-di-acetate; CBN, cannabinol; EI, Electronic Impact; ESI, Electrospray Injection; HHC, Hexahydrocannabinol; GC, gas chromatography, HPLC, High-Pressure Liquid Chromatography; MS, mass spectrometry; PDA, photodiode array; QTrap, quadrupole tandem ion trap; SFC, Supercritical Fluid Chromatography; THC-O, tetrahydrocannabinol acetate; THCP, Tetrahydrocannabiphorol; UV, Ultra Violet.