cis-(-)-Heptadeca-1,9-dien-4,6-diyn-3-ol

Base Information

• Chemical Name: cis-(-)-Heptadeca-1,9-dien-4,6-diyn-3-ol
• CAS No.: 21852-80-2
• Molecular Formula: C17H24O
• Molecular Weight: 244.377
• Hs Code.: 2905290000
• Nikkaji Number: J1.106.214H,J935.487E
• Wikipedia: Falcarinol
• Mol file: 21852-80-2.mol

Synonyms:falcarinol;falcarinol, (Z)-isomer;panaxynol

Chemical Property of cis-(-)-Heptadeca-1,9-dien-4,6-diyn-3-ol

Chemical Property:

• Vapor Pressure: 5.3E-07mmHg at 25°C
• Refractive Index: 1.507
• Boiling Point: 370.58 °C at 760 mmHg
• PKA: 11.66±0.20(Predicted)
• Flash Point: 163.37 °C
• PSA: 20.23000
• Density: 0.931 g/cm³
• LogP: 3.84690
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 9
• Exact Mass: 244.182715385
• Heavy Atom Count: 18
• Complexity: 363

Purity/Quality:

≥98% ^*data from raw suppliers

(R)-(-)-Falcarinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: CCCCCCCC=CCC#CC#CC(C=C)O
• Isomeric SMILES: CCCCCCC/C=C/CC#CC#CC(C=C)O
• Uses: (R)-(-)-Falcarinol is a covalent cannabinoid (CB1) receptor antagonist that induces pro-allergic effects on skin, and is most commonly found in the extracts of carrots. (R)-(-)-Falcarinol is also being used to induce apoptosis on human lymphoid leukaemia cell lines.

Technology Process of cis-(-)-Heptadeca-1,9-dien-4,6-diyn-3-ol

There total 10 articles about cis-(-)-Heptadeca-1,9-dien-4,6-diyn-3-ol 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: 69.0%

(Z)-1-chlorodec-2-ene (135457-18-0) + (3R)-hept-1-ene-4,6-diyn-3-ol (405144-99-2) → falcarinol (21852-80-2)

Guidance literature:

(3R)-hept-1-ene-4,6-diyn-3-ol; With copper(l) iodide; tetrabutyl-ammonium chloride; potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h;

(Z)-1-chlorodec-2-ene; In N,N-dimethyl-formamide; at 20 ℃; for 8h; Further stages.;

DOI:10.1021/jo020073w

Reference yield: 40.0%

(+/-)-3-acetoxyheptadeca-1,9Z-diene-4,6-diyne (1262023-34-6) → (-)-3-acetoxyheptadeca-1,9Z-diene-4,6-diyne (1262023-37-9) + falcarinol (21852-80-2)

Guidance literature:

With immobilised Candida antarctica lipase B; water; In acetone; at 20 ℃; for 43h; pH=7.4; optical yield given as %ee; enantioselective reaction; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1016/j.tet.2010.10.049

Reference yield:

2-decyn-1-ol (4117-14-0) → falcarinol (21852-80-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 86 percent / H₂; quinoline; KOH / Lindlar catalyst / ethanol / 16 h / atmospheric pressure

2.1: 81 percent / PPh₃; CCl₄ / 16 h / 80 °C

3.1: Bu₄N⁽¹⁺⁾*Cl^(1-); K₂CO₃; CuI / dimethylformamide / 0.25 h / 20 °C

3.2: 69 percent / dimethylformamide / 8 h / 20 °C

With quinoline; tetrachloromethane; potassium hydroxide; copper(l) iodide; tetrabutyl-ammonium chloride; hydrogen; potassium carbonate; triphenylphosphine; Lindlar's catalyst; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo020073w

upstream raw materials:

(Z)-1-chlorodec-2-ene

(3R)-hept-1-ene-4,6-diyn-3-ol

(Z)-2-decen-1-ol

2-decyn-1-ol

Downstream raw materials:

falcarinone

(-)-3-Hydroxy-heptadecan

Refernces

• 1、 Mayer, Sandra F.,Steinreiber, Andreas,Orru, Romano V. A.,Faber, Kurt. "Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-panaxytriol and (R)- and (S)-falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction". . p. 9115 - 9121. Retrieved 2007/10/03.