(-)-Nootkatone

Base Information

• Chemical Name: (-)-Nootkatone
• CAS No.: 38427-78-0
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.339
• UNII: ZMS1VJK5HY
• DSSTox Substance ID: DTXSID20904531
• Wikidata: Q27295748
• Mol file: 38427-78-0.mol

Synonyms:(-)-Nootkatone;Nootkatone, (-)-;UNII-ZMS1VJK5HY;ZMS1VJK5HY;38427-78-0;2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4S,4aR,6S)-;Nootkatone (7CI);(4S,4aR,6S)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one;1(10),11-Eremophiladien-2-one;4betaH,5alpha-Eremorphila-1(10)11-dien-2-one;starbld0001020;4Betah,5alpha-eremophila-1(10),11-dien-2-one;5,6-Dimethyl-8-isopropenylbicyclo(4.4.0)dec-1-en-3-one;5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one;SCHEMBL335639;DTXSID20904531;(4R,4aS)-dimethyl-6R-isopropenyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one;(4R - (4a,4aa,6b)) - 4,4a,5,6,7,8 - hexahydro - 4,4a - dimethyl - 6 - (1 - methylvinyl)naphthalen - 2(3H) - one;(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone;2(3h)-naftalenona, 4,4a,5,6,7,8-hexahidro-4,4a-dimetil-6-(1-metiletenil)-, (4r,4as,6r)-;AKOS024286995;Q27295748

Chemical Property of (-)-Nootkatone

Chemical Property:

• Boiling Point: 122 - 123 °C (1 mmHg)
• PSA: 17.07000
• LogP: 3.90420
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 218.167065321
• Heavy Atom Count: 16
• Complexity: 364

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(=O)C=C2C1(CC(CC2)C(=C)C)C
• Isomeric SMILES: C[C@H]1CC(=O)C=C2[C@@]1(C[C@H](CC2)C(=C)C)C

Technology Process of (-)-Nootkatone

There total 3 articles about (-)-Nootkatone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ (+)-nootkatone (4674-50-4,20107-31-7,26784-68-9,26785-08-0,27621-99-4,28834-25-5,34181-41-4,38427-78-0,38906-83-1,91416-23-8)

Guidance literature:

Alkohol 4, Alkohol 5, K-Dichromat (Oxid.);

DOI:10.1021/jf60220a054

Reference yield:

Acetic acid 1-methyl-1-((1R,3R)-3-methyl-4-oxo-cyclohexyl)-ethyl ester → 7-epi-nootkatone (4674-50-4,20107-31-7,26784-68-9,26785-08-0,27621-99-4,28834-25-5,34181-41-4,38427-78-0,38906-83-1,91416-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene

2: (i) NaNH₂, liq. NH₃, Ph₃CH, 1,2-dimethoxy-ethane, (ii) /BRN= 506057/, (iii) KOH, MeOH

In toluene;

Reference yield:

cis-2-Methyl-4-isopropenyl-cyclohexanon (6750-66-9,34181-39-0,52522-44-8,67814-84-0,118710-90-0) + trans-3-penten-2-one (3102-33-8) → 7-epi-nootkatone (4674-50-4,20107-31-7,26784-68-9,26785-08-0,27621-99-4,28834-25-5,34181-41-4,38427-78-0,38906-83-1,91416-23-8)

Guidance literature:

Multistep reaction; (i) NaNH₂, liq. NH₃, Ph₃CH, 1,2-dimethoxy-ethane, (ii) /BRN= 506057/, (iii) KOH, MeOH;

upstream raw materials:

cis-2-Methyl-4-isopropenyl-cyclohexanon

trans-3-penten-2-one

Downstream raw materials:

11R-urodiolenone

11S-urodiolenone

urodiolenone

α-Vetivon