21653-18-9

Basic information

• Product Name: (1S,5α)-4α-Methyl-1α-isopropylbicyclo[3.1.0]hexan-3β-ol
• Synonyms: (-)-3-Neothujol
• CAS NO: 21653-18-9
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.24932
• Mol File: 21653-18-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S,5α)-4α-Methyl-1α-isopropylbicyclo[3.1.0]hexan-3β-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,5α)-4α-Methyl-1α-isopropylbicyclo[3.1.0]hexan-3β-ol(21653-18-9)
• EPA Substance Registry System: (1S,5α)-4α-Methyl-1α-isopropylbicyclo[3.1.0]hexan-3β-ol(21653-18-9)

Safety Data

• Hazardous Substances Data: 21653-18-9(Hazardous Substances Data)

Upstream product

• 1125-12-8 (-)-α-thujone 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 471-15-8 (+)-isothujone 
• 59503-88-7 (+/-)-3-Isothujanol-p-nitrobenzoat 
• 7788-93-4 (-)-Isothujanol-p-toluolsulfonat 

Downstream Products

• 1125-12-8 (-)-α-thujone 
• 563-34-8 α-thujene 
• 7788-93-4 (-)-Isothujanol-p-toluolsulfonat 
• 2553-61-9 (1S,4S)-thujan-3-one-(2,4-dinitro-phenylhydrazone); (+)-isothujone-(2,4-dinitro-phenylhydrazone) 
• 40267-59-2 (+)-isothujone oxime 
• 40267-59-2 (-)-thujone oxime 

Relevant articles and documents

Synthesis and evaluation of apoptotic induction of human cancer cells by ester derivatives of thujone

Thujone (1), thujol (2), and aromatic thujol esters (3–9) were evaluated for their ability to induce cell death in human cervical (HeLa), melanoma (A375), and colon (HCT-116) cancer cell lines, using etoposide as a positive control. The compounds showed dose-dependent activity at concentrations ranging from 50–400 μg/mL. Etoposide exhibited an IC50 value of 116 μg/mL in HeLa cells, and α-thujone, α/β-thujone (7:1), and thujol showed comparable activity with IC50 values of 191, 198, and 136 μg/mL, respectively. All seven ester derivatives were cytotoxic to HeLa and HCT-116 cells, while a subset was cytotoxic to A375 cells. In HeLa cells, t-cinnamate (4), t-isonicotinate (5), t-nicotinate (6), and t-furoate (8) were more potent than either α-thujone or α/β-thujone. Similarly, t-furoate (8) was more potent than thujone in A375 cells, and t-isonicotinate (5) and t-nicotinate (6) were more potent against HCT-116 cells. Based on cell morphology, PARP cleavage and an increase in the caspase-3/7 levels, the esters exert their cytotoxic effects by induction of apoptosis.

(-) 3 Isothujone, a small nonnitrogenous molecule with antinociceptive activity in mice

(-) 3 isothujone and (+) 3 thujone were examined for antinociceptive activity using the hot plate and Nilsen tests. In the hot plate test (-) 3 isothujone (ED50 = 6.5 mg/kg) was found to be codeine like and equipotent with (-) Δ9 tetrahydrocannabinol while the racemic material was essentially half as potent as the levorotatory isomer. (+) 3 Thyjone was inactive in both antinociceptive tests as were several structural analogues of the 3 thujones. As with the THC's less antinociceptive activity was observed in the Nilsen test than in the hot plate assay. Acute toxicities for the 3 thujones were determined and vastly improved synthetic procedures have been developed for two long known but difficultly accessible 3 thujanols.