[(4R)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol

Base Information

• Chemical Name: [(4R)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol
• CAS No.: 57717-97-2
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• ChEMBL ID: CHEMBL1593539
• DSSTox Substance ID: DTXSID901315388
• Metabolomics Workbench ID: 47186
• Nikkaji Number: J86.013A
• Wikidata: Q105177714
• Mol file: 57717-97-2.mol

Synonyms:(+)-PERILLYL ALCOHOL;57717-97-2;(R)-Perillyl alcohol;[(4R)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol;d-perillyl alcohol;(R)-p-Mentha-1,8-dien-7-ol;(R)-(+)-perillyl alcohol;[(4R)-4-prop-1-en-2-ylcyclohexen-1-yl]methanol;(R)-(4-(Prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol;(+)perillyl alcohol;(4R)-perillyl alcohol;UPCMLD-DP082;CHEMBL1593539;SCHEMBL15681915;UPCMLD-DP082:001;CHEBI:145806;NDTYTMIUWGWIMO-JTQLQIEISA-N;DTXSID901315388;AKOS006237377;NCGC00161638-01;C22272;EN300-26276323;(R)-4-(1-Methylethenyl)-1-cyclohexene-1-methanol;J-500062;4-(1-Methylethenyl)-(4R)-1-Cyclohexene-1-methanol

Chemical Property of [(4R)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol

Chemical Property:

• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.491
• Boiling Point: 241.2°Cat760mmHg
• PKA: 14.85±0.10(Predicted)
• Flash Point: 99.6°C
• PSA: 20.23000
• Density: 0.94g/cm³
• LogP: 2.28130
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 179

Purity/Quality:

99% ^*data from raw suppliers

(+)-Perillylalcohol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC(=CC1)CO
• Isomeric SMILES: CC(=C)[C@@H]1CCC(=CC1)CO
• Uses: (+)-Perillyl alcohol is a monoterpene that is cytotoxic to glioma cells.

Technology Process of [(4R)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol

There total 36 articles about [(4R)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol 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: 96.0%

L-perillaldehyde (5503-12-8) → (R)-Perillyl alcohol (57717-97-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jo062630a

Reference yield: 43.0%

C12H18O2 → (R)-Perillyl alcohol (57717-97-2)

Guidance literature:

C₁₂H₁₈O₂; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 110 ℃; for 15h; Inert atmosphere; Sealed tube;

With methanol; potassium carbonate; at 20 ℃;

DOI:10.1016/j.tetlet.2014.01.039

Reference yield: 32.0%

D-limonene (5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3) → (R)-9-hydroxy-p-mentha-1,8(10)-diene (38142-45-9) + (R)-Perillyl alcohol (57717-97-2) + C20H30

Guidance literature:

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium sulfite; In hexane; water; at -20 - 20 ℃;

DOI:10.1071/CH01168

upstream raw materials:

D-limonene

(+)-acetic acid p-mentha-1,8-dien-7-yl ester

(1R)-Myrtenol

7-hydroxy-α-terpineol

Downstream raw materials:

(R)-perillyl 1-(trimethylsilyl)vinyl ether

(+)-acetic acid p-mentha-1,8-dien-7-yl ester

C₁₂H₁₆Cl₃NO

C₁₈H₂₄BrNO₄S

Refernces

• 1、 McAulay, Kirsten,Clark, J. Stephen. "Total Synthesis of 7-epi-Pukalide and 7-Acetylsinumaximol B". . p. 9761 - 9765. Retrieved 2017/07/25.
• 2、 Mlodzik, Jacek,Wrblewska, Agnieszka,Makuch, Edyta,Wrbel, Rafal J.,Michalkiewicz, Beata. "Fe/EuroPh catalysts for limonene oxidation to 1,2-epoxylimonene, its diol, carveol, carvone and perillyl alcohol". . p. 111 - 120. Retrieved 2016/04/26.