SOLANESOL

Base Information

• Chemical Name: SOLANESOL
• CAS No.: 540-03-4
• Molecular Formula: C₄₅H₇₄O
• Molecular Weight: 631.082
• Hs Code.: 2905229000
• Mol file: 540-03-4.mol

Synonyms:SOLANESOL(P)

Chemical Property of SOLANESOL

Chemical Property:

• Boiling Point: 685.6oC at 760 mmHg
• Flash Point: 130.2oC
• PSA: 20.23000
• Density: 0.889 g/cm3
• LogP: 14.75690
• Storage Temp.: −20°C

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of SOLANESOL

There total 35 articles about SOLANESOL 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: 88.0%

1-((2Z,6Z,10Z,14Z,18Z,22Z,26E,30E)-1-Benzyloxy-3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaene-13-sulfonyl)-4-methyl-benzene (92464-91-0) → solanesol (15639-69-7,540-03-4)

Guidance literature:

With lithium; In diethyl ether; at -76 ℃;

DOI:10.1246/cl.1984.1105

Reference yield: 50.0%

(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethyl-5-p-tolylsulphonylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-ol → solanesol (13190-97-1,540-03-4)

Guidance literature:

With lithium; ethylamine; In diethyl ether; at -78 ℃;

DOI:10.1039/P19810000761

Reference yield:

3,7-dimethyl-2E,6-octadien-1-yl acetate (105-87-3,8022-83-1) → solanesol (13190-97-1,540-03-4)

Guidance literature:

Multi-step reaction with 14 steps

1: 44 percent / SeO₂ / aq. ethanol / 9 h / Heating

2: 72 percent / NaBH₄ / methanol / 5 h / -10 °C

3: 94 percent / PBr₃, pyridine / diethyl ether / 6 h / 0 °C

4: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h

5: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C

6: 91 percent / PBr₃, pyridine / diethyl ether / 6 h / -5 °C

7: 78 percent / dimethylformamide / 24 h / Ambient temperature

8: 1.) n-BuLi, 3.) H₂O, KOH

9: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C

10: 1.) PBr₃, pyridine / 1.) ether, 2.) DMF, ambient temperature

11: 1.) n-BuLi, 3.) H₂O, KOH

12: 70 percent / Li, ethylamine / diethyl ether

13: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C

14: 50 percent / Li, ethylamine / diethyl ether / -78 °C

With pyridine; potassium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; selenium(IV) oxide; water; phosphorus tribromide; lithium; ethylamine; In methanol; diethyl ether; ethanol; N,N-dimethyl-formamide;

DOI:10.1039/P19810000761

upstream raw materials:

(2E,6E)-3,7,11-trimethyl-1-(p-tolylsulfonyl)dodeca-2,6,10-triene

(2E,6E,10E)-1-Benzyloxy-3,7,11-trimethyldodeca-2,6,10-trien-12-ol

(2E,6E,10E)-2,6,10-trimethyl-12-(toluene-4-sulfonyl)-dodeca-2,6,10-trien-1-ol

3,7-dimethyl-2E,6-octadien-1-yl acetate

Downstream raw materials:

2-methyl-3-((2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35- nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl)naphthalene-1,4-dione

chloro-acetic acid 3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl ester

4-oxopentanal

Malloprenol - p - brombenzoat

Refernces

• 1、 -. "β,γ-dihydropolyprenyl alcohol derivatives and pharmaceutical composition containing a polyprenyl compound". . . Retrieved 2008/06/13.
• 2、 Sato, Kikumasa,Inoue, Seiichi,Onishi, Akira,Uchida, Nobuhiko,Minowa, Nobuto. "Stereoselective Synthesis of Solanesol and all-trans-Decaprenol". . p. 761 - 769. Retrieved 2007/10/02.