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Cas Database

76231-76-0

76231-76-0

Identification

  • Product Name:Bicyclo[3.1.0]hexan-3-one,4-methyl-1-(1-methylethyl)-, (1S,5R)-

  • CAS Number: 76231-76-0

  • EINECS:

  • Molecular Weight:152.236

  • Molecular Formula: C10H16O

  • HS Code:2914299000

  • Mol File:76231-76-0.mol

Synonyms:Bicyclo[3.1.0]hexan-3-one,4-methyl-1-(1-methylethyl)-, [1S-(1a,5a)]-; a,b-Thujone

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Safety information and MSDS view more

  • Pictogram(s):

  • Hazard Codes:T

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowedH311 Toxic in contact with skin H315 Causes skin irritation H317 May cause an allergic skin reaction H319 Causes serious eye irritation H331 Toxic if inhaled H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
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  • Manufacture/Brand:TRC
  • Product Description:α,β-Thujone
  • Packaging:50mg
  • Price:$ 610
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:α,β-Thujone
  • Packaging:25mg
  • Price:$ 340
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:α,β-Thujone technical, ~70% α-thujone basis, ~10% β-thujone basis
  • Packaging:50ml
  • Price:$ 330
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:α,β-Thujone technical, ~70% α-thujone basis, ~10% β-thujone basis
  • Packaging:10ml
  • Price:$ 95.6
  • Delivery:In stock
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Relevant articles and documentsAll total 2 Articles be found

A six-step total synthesis of α-thujone and: D 6-α-thujone, enabling facile access to isotopically labelled metabolites

Thamm, Irene,Richers, Johannes,Rychlik, Michael,Tiefenbacher, Konrad

, p. 11701 - 11703 (2016/10/04)

The short synthesis of α-thujone relies on the functionalization of the readily available dimethylfulvene. Furthermore, the three main metabolites of the natural product were also synthesized. Since d6-acetone can be used as a starting material, the route developed allows for the facile incorporation of isotopic labels which are required for detecting and quantifying trace amounts via GC/MS analysis.

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

Rice,Wilson

, p. 1054 - 1057 (2007/10/13)

(-) 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.

Process route upstream and downstream products

Process route

Conditions
Conditions Yield
1-isopropylbicyclo[3.1.0]hexan-3-one; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;
methyl iodide; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; toluene; at -78 ℃; for 2h;
75%
Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: diethylzinc / hexane; dichloromethane / 0.17 h / 0 °C
1.2: 16 h / 0 - 20 °C
2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 4 h / 20 °C
3.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C
3.2: 2 h / -78 °C
With diethylzinc; potassium hexamethylsilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; toluene; 1.1: |Simmons-Smith Cyclopropanation / 1.2: |Simmons-Smith Cyclopropanation;
Conditions
Conditions Yield
Multi-step reaction with 5 steps
1.1: pyrrolidine / methanol / 2 h / 0 - 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2.2: 17 h / 0 - 20 °C
2.3: 24 h / 20 °C
3.1: diethylzinc / hexane; dichloromethane / 0.17 h / 0 °C
3.2: 16 h / 0 - 20 °C
4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 4 h / 20 °C
5.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C
5.2: 2 h / -78 °C
With pyrrolidine; lithium aluminium tetrahydride; diethylzinc; potassium hexamethylsilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; 3.1: |Simmons-Smith Cyclopropanation / 3.2: |Simmons-Smith Cyclopropanation;
Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 4 h / 20 °C
2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C
2.2: 2 h / -78 °C
With potassium hexamethylsilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide; toluene;
Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
1.2: 17 h / 0 - 20 °C
1.3: 24 h / 20 °C
2.1: diethylzinc / hexane; dichloromethane / 0.17 h / 0 °C
2.2: 16 h / 0 - 20 °C
3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 4 h / 20 °C
4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C
4.2: 2 h / -78 °C
With lithium aluminium tetrahydride; diethylzinc; potassium hexamethylsilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; toluene; 2.1: |Simmons-Smith Cyclopropanation / 2.2: |Simmons-Smith Cyclopropanation;
(1S,5R)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
76231-76-0

(1S,5R)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-one

(1R-(1α,2α/β,6α))-2-methyl-6-(1-methylethyl)bicyclo-[4.1.0]heptan-3-one
178686-04-9

(1R-(1α,2α/β,6α))-2-methyl-6-(1-methylethyl)bicyclo-[4.1.0]heptan-3-one

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 70 percent / boron trifluoride etherate / diethyl ether / Ambient temperature
2: 96 percent / aq. sodium chloride / dimethylsulfoxide / 4 h / 140 °C
With boron trifluoride diethyl etherate; sodium chloride; In diethyl ether; dimethyl sulfoxide;
Conditions
Conditions Yield
With potassium hydroxide; In methanol; at 0 ℃; for 5h;
100%
(1S,5R)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
76231-76-0

(1S,5R)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-one

4β-(Hydroxymethyl)-thujan-3-one
74418-34-1

4β-(Hydroxymethyl)-thujan-3-one

Conditions
Conditions Yield
With potassium hydroxide; In methanol; at 0 ℃; for 4.5h;
100%

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  • Finetech Industry Limited
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  • Debye Scientific
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  • LEAP CHEM Co., Ltd.
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  • Sigma-Aldrich Chemie GmbH
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