d-Piperitone

Base Information

• Chemical Name: d-Piperitone
• CAS No.: 6091-50-5
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• Hs Code.: 2916310090
• European Community (EC) Number: 639-124-0
• UNII: 8ZZ2GU5WBU
• DSSTox Substance ID: DTXSID401317272
• Nikkaji Number: J564.480A
• Wikidata: Q27105210
• Metabolomics Workbench ID: 28112
• Mol file: 6091-50-5.mol

Synonyms:d-Piperitone;6091-50-5;(+)-Piperitone;PIPERITONE, D-;Piperitone, alpha-;d-Piperitone (natural);FEMA No. 2910;(-)-piperitone;UNII-8ZZ2GU5WBU;8ZZ2GU5WBU;(6S)-3-methyl-6-propan-2-ylcyclohex-2-en-1-one;4-Isopropyl-1-methyl-1-cyclohexen-3-one;3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-one, (S)-;2-Cyclohexen-1-one, 3-methyl-6-(1-methyethyl)-, (S)-;2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (S)-;(6S)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one;(R)-Piperitone;p-Menth-1-en-3-one, ()-;alpha-Piperitone;dextro-piperitone;(S)-piperitone;(6R)-6-isopropyl-3-methylcyclohex-2-en-1-one;(S)-(+)-Piperitone;(6R)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-one;CHEBI:41;D-PIPERITONE [FHFI];2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (6S)-;SCHEMBL1248697;DTXSID401317272;FEMA NO. 2910, D-;AKOS006271898;LMPR0102090024;LS-3054;(S)-6-isopropyl-3-methylcyclohex-2-enone;2-AMINO-4,4,4-TRIFLUOROBUTYRICACID;C09885;(S)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-one;Q27105210

Chemical Property of d-Piperitone

Chemical Property:

• Vapor Pressure: 0.0572mmHg at 25°C
• Refractive Index: 1.4884 (estimate)
• Boiling Point: 233°C at 760 mmHg
• Flash Point: 90.9°C
• PSA: 17.07000
• Density: 0.915g/cm³
• LogP: 2.56780
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 189

Purity/Quality:

99% ^*data from raw suppliers

(-)-Piperitone 97 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C(CC1)C(C)C
• Isomeric SMILES: CC1=CC(=O)[C@@H](CC1)C(C)C

Technology Process of d-Piperitone

There total 8 articles about d-Piperitone 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: 60.0%

(2R,5S)-menthone (10458-14-7,14073-97-3,17627-49-5,7786-64-3) → (S)-(+)-piperitone (4573-50-6,6091-52-7,89-81-6,6091-50-5)

Guidance literature:

(2R,5S)-menthone; With bis(2,2,6,6-tetramethyl-1-piperidyl)zinc; In toluene; at 0 ℃; for 0.166667h; Inert atmosphere;

With bis(η3-allyl-μ-chloropalladium(II)); allyl diethyl phosphate; In toluene; at 0 - 120 ℃; for 0.5h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.7b03818

Reference yield: 58.0%

(2S,5R)-6-phenylselenenylmenthone (142835-88-9) → (S)-(+)-piperitone (4573-50-6,6091-52-7,89-81-6,6091-50-5)

Guidance literature:

With dihydrogen peroxide; magnesium sulfate; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80539-1

Reference yield:

3-terpinolenone (491-09-8) → piperitone (89-81-6,6091-52-7) + l-menthone (3391-87-5,17627-49-5,7786-64-3) + (2R,5S)-menthone (10458-14-7,14073-97-3,17627-49-5,7786-64-3) + (S)-(+)-piperitone (4573-50-6,6091-52-7,89-81-6,6091-50-5) + (1S,4S)-isomenthone (18309-28-9,17627-49-5,7786-64-3) + (1R,4R)-(+)-isomenthone (1196-31-2,17627-49-5,7786-64-3)

Guidance literature:

With hydrogen; HRuCl(TBPC)2; In toluene; at 65 ℃; for 26h; under 7600 Torr; Mechanism; Product distribution; asymmetric synthesis, var. chiral ruthenium catalyst, variation of time;

DOI:10.1016/S0040-4020(01)85919-6

upstream raw materials:

3-terpinolenone

(3R,6S)-3-methyl-6-(prop-2-yl)-1-trimethylsilyloxy-cyclohexene

(2S,5R)-6-phenylselenenylmenthone

(2R,5S)-menthone

Downstream raw materials:

(1S,4S)-isomenthone

thymol

cis-2,3,3-Trimethyl-6-(1-methylethyl)-1-cyclohexanon

5,5-Dimethyl-2-(1-methylethyl)-2-(2-propenyl)-1-cyclohexanon