2-[(1r,2r,5r)-5-Hydroxy-2-(3-hydroxypropyl)cyclohexyl]-5-(2-methyloctan-2-yl)phenol

Base Information

• Chemical Name: 2-[(1r,2r,5r)-5-Hydroxy-2-(3-hydroxypropyl)cyclohexyl]-5-(2-methyloctan-2-yl)phenol
• CAS No.: 83002-04-4
• Deprecated CAS: 86687-39-0
• Molecular Formula: C₂₄H₄₀O₃
• Molecular Weight: 376.58
• UNII: KFY70972J5,8YX8JK1BQG
• DSSTox Substance ID: DTXSID401017713,DTXSID80875516
• Nikkaji Number: J259.891D
• Wikipedia: CP_55,940
• Wikidata: Q5013768
• Pharos Ligand ID: KGVC1UMRSBFW
• ChEMBL ID: CHEMBL559612
• Mol file: 83002-04-4.mol

Synonyms:3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol;CP 55940;CP 56667;CP-55,940;CP-56,667;CP55,940;CP55940

Chemical Property of 2-[(1r,2r,5r)-5-Hydroxy-2-(3-hydroxypropyl)cyclohexyl]-5-(2-methyloctan-2-yl)phenol

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 1.36E-10mmHg at 25°C
• Melting Point: 65-68 °C
• Refractive Index: 1.526
• Boiling Point: 494.4 °C at 760 mmHg
• PKA: 10.25±0.40(Predicted)
• Flash Point: 209.2 °C
• PSA: 60.69000
• Density: 1.026 g/cm³
• LogP: 5.65730
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 15 mg/mL, soluble
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 376.29774513
• Heavy Atom Count: 27
• Complexity: 408

Purity/Quality:

98%,99%, ^*data from raw suppliers

CP-55940 >98% (HPLC), powder ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCC(C)(C)C1=CC(=C(C=C1)C2CC(CCC2CCCO)O)O
• Isomeric SMILES: CCCCCCC(C)(C)C1=CC(=C(C=C1)[C@@H]2C[C@@H](CC[C@H]2CCCO)O)O
• Uses: CP 55,940 is a cannabinoid agonist which is considerably more potent than Δ9-THC in both behavioral tests and receptor binding assays. Displays high and roughly equal affinity for both central and peripheral cannabinoid receptors (Ki = 0.6 - 5.0 and 0.7 - 2.6 nM at CB1 and CB2 respectively; EC50 values are 0.2, 0.3 and 5 nM at CB1, CB2 and GRP55 respectively). Controlled substance. (+)-CP 55940 is the enantiomer of (C781415), a cannabinoid agonist. Both CP 55,940 and (+)-CP 55940 bind to CB receptors but only CP-55,940 elicits a biological response via the receptors. However, ( +)-CP 55940 shows the same antinociceptive effects as its enantiomer. CP-55940 has been used as a cannabinoid agonists in Chinese hamster ovary (CHO) expressing cannabinoid receptor 2(CB2).

Technology Process of 2-[(1r,2r,5r)-5-Hydroxy-2-(3-hydroxypropyl)cyclohexyl]-5-(2-methyloctan-2-yl)phenol

There total 30 articles about 2-[(1r,2r,5r)-5-Hydroxy-2-(3-hydroxypropyl)cyclohexyl]-5-(2-methyloctan-2-yl)phenol 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: 90.0%

(1R,3R,4R)-3-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-4-(3-hydroxypropyl)cyclohexanol (866398-11-0) → CP 55,940 (83002-04-4,83002-05-5)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; 1-thiopropane; In hexane; at 100 - 120 ℃; for 5h;

DOI:10.1021/ol051570c

Reference yield:

cis-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-trans-4-(3-hydroxypropyl)cyclohexanol → (-)-cis-3-[2-Hydroxy-4-(1,1-dimethylheptyl)phenyl]-trans-4-(3-hydroxypropyl)-cyclohexanol (83002-04-4,83002-05-5)

Guidance literature:

palladium-carbon; In ethanol; di-isopropyl ether; water;

Reference yield:

trans-4-(3-hydroxypropyl)-cis-3-[2-hydroxy-4-(1,1-dimethyl-cis-2-heptenyl)phenyl]cyclohexanol → (-)-cis-3-[2-Hydroxy-4-(1,1-dimethylheptyl)phenyl]-trans-4-(3-hydroxypropyl)-cyclohexanol (83002-04-4,83002-05-5)

Guidance literature:

palladium; In tetrahydrofuran;

upstream raw materials:

(1R,3R,4R)-3-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-4-(3-hydroxypropyl)cyclohexanol

trifluoromethanesulfonic acid 3-(1,1-dimethylheptyl)-5-methoxyphenyl ester

trifluoromethanesulfonic acid 4-(1,1-dimethylheptyl)-2,6-dimethoxyphenyl ester

(1R,4R,5R,8S)-4-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-8-methoxymethoxybicyclo[3.3.1]non-3-en-2-one

Refernces

• 1、 Itagaki, Noriaki,Sugahara, Tsutomu,Iwabuchi, Yoshiharu. "Expedient synthesis of potent cannabinoid receptor agonist (-)-CP55,940". . p. 4181 - 4183. Retrieved 2007/10/03.