Solanesol

Base Information

• Chemical Name: Solanesol
• CAS No.: 13190-97-1
• Deprecated CAS: 111820-07-6,540-03-4
• Molecular Formula: C45H74O
• Molecular Weight: 631.082
• Hs Code.: 29052900
• European Community (EC) Number: 603-532-7
• NSC Number: 299938
• UNII: FF31XTR2N4
• DSSTox Substance ID: DTXSID60884580
• Nikkaji Number: J161.432K,J24.975K
• Wikipedia: Solanesol
• Wikidata: Q26841010
• Metabolomics Workbench ID: 123648
• ChEMBL ID: CHEMBL1567436
• Mol file: 13190-97-1.mol

Synonyms:(C45 all trans polyprenol);solanesol

Chemical Property of Solanesol

Chemical Property:

• Appearance/Colour: brown waxy solid
• Vapor Pressure: 9.21E-22mmHg at 25°C
• Melting Point: 33 °C
• Refractive Index: 1.506
• Boiling Point: 685.6 °C at 760 mmHg
• PKA: 14.42±0.10(Predicted)
• Flash Point: 130.2 °C
• PSA: 20.23000
• Density: 0.889 g/cm³
• LogP: 14.75690
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 15.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 25
• Exact Mass: 630.57396698
• Heavy Atom Count: 46
• Complexity: 1100

Purity/Quality:

99% ^*data from raw suppliers

Solanesol(~90%) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCCC(=CCO)C)C)C)C)C)C)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CC/C(=C/CC/C(=C/CC/C(=C/CC/C(=C/CC/C(=C/CC/C(=C/CO)/C)/C)/C)/C)/C)/C)/C)/C)C
• Uses: It is an important raw material for the synthesis of coenzyme Q10. The coenzyme Q10 can be acted as the activator of the human cell respiration and metabolism and the immune enhancer of the body. It can be acted as the intermediate of coenzyme Q10 and vitamin K2. C45 class isopentenol is the most surplus fat in the tobacco leaf and is a important precursor of the tumorigenicity poly nuclear aromatic hydrocarbons in the tobacco. It is an important pharmaceutical intermediate. It has anti-ulcer and anti-tumor property. antioxidant, antibacterial A high molecular weight isoprenoid alcohol isolated from tobacco leaf Tracer for environmental exposure to tobacco smoke.

Technology Process of Solanesol

There total 19 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: 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

Reference yield:

(2E,6E)-8-bromo-3,7-dimethylocta-2,6-dienyl acetate (37905-04-7) → solanesol (13190-97-1,540-03-4)

Guidance literature:

Multi-step reaction with 11 steps

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

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

3: 91 percent / PBr₃, pyridine / diethyl ether / 6 h / -5 °C

4: 78 percent / dimethylformamide / 24 h / Ambient temperature

5: 1.) n-BuLi, 3.) H₂O, KOH

6: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C

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

8: 1.) n-BuLi, 3.) H₂O, KOH

9: 70 percent / Li, ethylamine / diethyl ether

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

11: 50 percent / Li, ethylamine / diethyl ether / -78 °C

With pyridine; potassium hydroxide; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; water; phosphorus tribromide; lithium; ethylamine; In methanol; diethyl ether; 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:

ubiquinone-45

3,4,5-triiodo-benzoic acid-(3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2t,6t,10t,14t,18t,22t,26t,30t,34-nonaenyl ester)

decaprenol

3,5-dinitro-benzoic acid-(3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2t,6t,10t,14t,18t,22t,26t,30t,34-nonaenyl ester)

Refernces

• 1、 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.