(+)-trans-Carveol

Base Information

• Chemical Name: (+)-trans-Carveol
• CAS No.: 18383-51-2
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• UNII: IU746IQW52
• DSSTox Substance ID: DTXSID001036410
• Nikkaji Number: J9.143J
• Wikidata: Q27089408
• Metabolomics Workbench ID: 50058
• Mol file: 18383-51-2.mol

Synonyms:(+)-trans-Carveol;(1R,5S)-carveol;Carveol, trans-(+)-;(4S,6R)-trans-Carveol;IU746IQW52;18383-51-2;UNII-IU746IQW52;p-Mentha-6,8-dien-2-ol, (2R,4S)-(+)-;(1R,5S)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ol;(1R,5S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol;2-Cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, (1R,5S)-;trans-Carveole;t-Carveol;(1R,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol;(E)-Carveol;(.+/-.)-trans-Carveol;trans-Mentha-1,8-dien-6-ol;trans-p-Mentha-1,8-dien-6-ol;5-Isopropenyl-2-methyl-2-cyclohexen-1-ol, trans-;trans-2-Methyl-5-[1-methylethenyl]-2-cyclohexen-1-ol;SCHEMBL18339543;CHEBI:15388;DTXSID001036410;Q27089408;(1S,5R)-2-methyl-5-prop-1-en-2-yl-cyclohex-2-en-1-ol

Chemical Property of (+)-trans-Carveol

Chemical Property:

• PSA: 20.23000
• LogP: 2.27970
• 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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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
• General Description: (1S,5R)-2-methyl-5-prop-1-en-2-yl-cyclohex-2-en-1-ol, also known as (-)-trans-carveol, is a valuable fragrance compound derived from the isomerization of α-pinene oxide. It can be selectively synthesized in high yields (up to 70%) using polar basic solvents like dimethylacetamide, with catalysts such as CeCl₃, SnCl₂, or phosphotungstic acid (H₃PW₁₂O₄₀). The solvent's basicity and polarity play a crucial role in directing the reaction toward trans-carveol rather than other isomers like trans-sobrerol or campholenic aldehyde. (1S,5R)-2-methyl-5-prop-1-en-2-yl-cyclohex-2-en-1-ol is industrially significant and can be efficiently produced through acid-catalyzed transformations, offering a practical route for fragrance applications.

Technology Process of (+)-trans-Carveol

There total 81 articles about (+)-trans-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: 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

upstream raw materials:

(R)-Carvone

aluminum isopropoxide

isopropyl alcohol

L-trans-pinocarveol

Downstream raw materials:

cis-(1R,5R)-5-isopropyl-2-methyl-2-cyclohexen-1-ol

(1R-cis)-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol acetate

trans carveol 3,5-dinitrobenzoate

(-)-cis-carveol 3,5-dinitrobenzoate