(-)-cis-Carveol

Base Information

• Chemical Name: (-)-cis-Carveol
• CAS No.: 2102-59-2
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• European Community (EC) Number: 218-270-5
• NSC Number: 319644
• UNII: OOZ105PLI9,DI8OD510EO
• DSSTox Substance ID: DTXSID60317646,DTXSID701036409
• Nikkaji Number: J9.138C
• Wikidata: Q27891515
• Metabolomics Workbench ID: 28118
• Mol file: 2102-59-2.mol

Synonyms:(-)-cis-Carveol;1197-06-4;2102-59-2;cis-(-)-Carveol;(+/-)-cis-Carveol;Carveol, cis-;(4R,6R)-cis-Carveol;Carveol, cis-(-)-;cis-Carveol;L-cis-Carveol;Carveol, cis-(+/-)-;DI8OD510EO;(Z)-Carveol;cis-Mentha-1,8-dien-6-ol;NSC-319644;(1R)-cis-Carveol;(1R,5R)-(-)-cis-Carveol;p-Mentha-6,8-dien-2-ol, cis-;(1R,5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ol;UNII-DI8OD510EO;OOZ105PLI9;cis-p-mentha-6,8-dien-2-ol;(-)-(4R,6R)-cis-carveol;2-Cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, (1R,5R)-rel-;(1R-cis)-2-Methyl-5-isopropenyl-2-cyclohexen-1-ol;cis-2-Methyl-5-(1-methylvinyl)-2-cyclohexene-1-ol;(4R,6R)-p-mentha-1,8-dien-6-ol;(1R-cis)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-ol;2-Cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, cis-;(Z)-carveol,2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol,cis-mentha-1,8-dien-6-ol;L-Carveol;2-Cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, (1R,5R)-;p-Mentha-6,8-dien-2-ol, (Z)-;p-Mentha-6, cis-;5-Isopropenyl-2-methyl-2-cyclohexen-1-ol, cis-;CARVEOL, L-CIS-;cis-2-Methyl-5-[1-methylethenyl]-2-cyclohexen-1-ol;UNII-OOZ105PLI9;2-Cyclohexen-1-ol, cis-;CHEBI:227;(-)-(4R,6R)-Carveol;SCHEMBL15011317;DTXSID60317646;DTXSID701036409;EINECS 218-270-5;NSC319644;(-)-cis-p-Mentha-1,8-dien-6-ol;(2R)-cis-p-mentha-6,8-dien-2-ol;LMPR0102090030;(-)-P-MENTHA-6,8-DIEN-2-OL;FEMA NO. 2247, CIS-(-)-;p-Mentha-6,8-dien-2-ol, (2R,4R)-(-)-;Q27891515;2-Methyl-5-(1-methylethenyl)-(1R,5R)-2-Cyclohexen-1-ol;2-Methyl-5-(1-methylethenyl)-(1R-cis)-2-Cyclohexen-1-ol;(1R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol;(1R,5R)-rel-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol;2-Cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, (1R-cis)-

Chemical Property of (-)-cis-Carveol

Chemical Property:

• Appearance/Colour: Colorless to pale yellow liquid
• Melting Point: 24-25 °C
• Refractive Index: n20/D 1.496(lit.)
• Boiling Point: 231.5 °C at 760 mmHg
• PKA: 14.60±0.60(Predicted)
• Flash Point: 91.2 °C
• PSA: 20.23000
• Density: 0.949g/cm³
• LogP: 2.27970
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 191

Purity/Quality:

99%, ^*data from raw suppliers

(-)-CARVEOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC(CC1O)C(=C)C
• Isomeric SMILES: CC1=CC[C@H](C[C@H]1O)C(=C)C

Technology Process of (-)-cis-Carveol

There total 25 articles about (-)-cis-Carveol 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: 94.0%

(R)-Carvone (6485-40-1,2244-16-8) → (4R,6R)-carveol (99-48-9,1197-06-4,1197-07-5,2102-58-1,2102-59-2,5157-78-8,5503-11-7,7632-16-8,18383-51-2,22567-18-6,20307-86-2) + (-)-trans-carveol (18383-51-2,22567-18-6,20307-86-2)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at -78 ℃; for 0.5h; Title compound not separated from byproducts.;

DOI:10.1002/ejoc.200700490

Reference yield: 85.0%

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) → (4R,6R)-carveol (99-48-9,1197-06-4,1197-07-5,2102-58-1,2102-59-2,5157-78-8,5503-11-7,7632-16-8,18383-51-2,22567-18-6,20307-86-2)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride;

DOI:10.1016/S0040-4039(00)96053-2

Reference yield: 65.0%

C19H18Co2O7 → (4R,6R)-carveol (99-48-9,1197-06-4,1197-07-5,2102-58-1,2102-59-2,5157-78-8,5503-11-7,7632-16-8,18383-51-2,22567-18-6,20307-86-2)

Guidance literature:

In N,N-dimethyl acetamide; at 60 ℃; under 760.051 Torr; Solvent; Inert atmosphere;

DOI:10.1002/adsc.202001311

upstream raw materials:

(R)-Carvone

aluminum isopropoxide

isopropyl alcohol

L-trans-pinocarveol

Downstream raw materials:

2,2-Dimethyl-propionic acid (1R,5R)-5-isopropenyl-2-methyl-cyclohex-2-enyl ester

(+)-neodihydrocarveol

(R)-Carvone

(4R,6R)-4-acetoxy-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-one

Refernces

• 1、 Chinna Ayya Swamy,Varenikov, Andrii,Ruiter, Graham De. "Chiral Imidazo[1,5- a]pyridine-Oxazolines: A Versatile Family of NHC Ligands for the Highly Enantioselective Hydrosilylation of Ketones". supporting information. p. 247 - 257. Retrieved 2020/02/04.
• 2、 Jang, Yoon Kyung,Magre, Marc,Rueping, Magnus. "Chemoselective Luche-Type Reduction of α,β-Unsaturated Ketones by Magnesium Catalysis". supporting information. p. 8349 - 8352. Retrieved 2019/10/16.