DECAPRENOL

Base Information

• Chemical Name: DECAPRENOL
• CAS No.: 15575-04-9
• Molecular Formula: C50H82 O
• Molecular Weight: 699.2
• Mol file: 15575-04-9.mol

Synonyms:2,6,10,14,18,22,26,30,34,38-Tetracontadecaen-1-ol,3,7,11,15,19,23,27,31,35,39-decamethyl-, (all-E)- (8CI); Solanesol 50 (7CI);Betuladecaprenol; Betulaprenol 10; Decaisoprenol, (all-E)-;all-E-Decaisoprenol; all-trans-Decaprenol

Chemical Property of DECAPRENOL

Chemical Property:

• Melting Point: 39.5-40.5 °C
• Boiling Point: 732.5±29.0 °C(Predicted)
• PKA: 14.42±0.10(Predicted)
• PSA: 20.23000
• Density: 0.890±0.06 g/cm3(Predicted)
• LogP: 16.48340

Purity/Quality:

99%, ^*data from raw suppliers

N-DECAPRENOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of DECAPRENOL

There total 26 articles about DECAPRENOL 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: 81.0%

(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyl-9-p-tolylsulphonyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-ol → decaprenol (15575-04-9)

Guidance literature:

With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); lithium triethylborohydride; In tetrahydrofuran; at 0 - 20 ℃; for 10h; Inert atmosphere;

DOI:10.1002/hlca.200890211

Reference yield:

solanesol (13190-97-1,540-03-4) → decaprenol (15575-04-9)

Guidance literature:

ueber mehrere Zwischenstufen;

DOI:10.1002/hlca.19590420733

Reference yield:

4-phenylsulfonyl-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2E,6E,10E,14E,18E,22E,26E,30E,34E,37-decaen-1-ol (116854-31-0) → decaprenol (15575-04-9) + 3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-3Z,6E,10E,14E,18E,22E,26E,30E,34E,38-decaen-1-ol (116909-56-9) + 3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-3E,6E,10E,14E,18E,22E,26E,30E,34E,38-decaen-1-ol (111729-66-9)

Guidance literature:

With dibenzo-18-crown-6; ammonia; sodium; In tetrahydrofuran; Yield given. Yields of byproduct given. Title compound not separated from byproducts; 1.) -70 deg C, 15 min, 2.) 15 min;

DOI:10.1007/BF00965388

upstream raw materials:

solanesol

(all-E)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl bromide

4-phenylsulfonyl-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2E,6E,10E,14E,18E,22E,26E,30E,34E,37-decaen-1-ol

3,7,11,15,19,23,27,31,35,39-decamethyl-1,6,10,14,18,22,26,30,34,38-tetracontadecaene-3-ol

Downstream raw materials:

ubidecarenone

C₅₉H₈₆⁽²⁾H₆O₄

4-acetoxy-6-decaprenyl-2,3,5-trimethylphenol

Acetic acid 3-((2Z,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyl-tetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl)-4-hydroxy-2,5,6-trimethyl-phenyl ester

Refernces

• 1、 Yu, Xiong-Jie,Zhang, Hao,Xiong, Fang-Jun,Chen, Xu-Xiang,Chen, Fen-Er. "An improved convergent strategy for the synthesis of oligoprenols". experimental part. p. 1967 - 1974. Retrieved 2009/02/07.
• 2、 Veselovskii, A. B.,Moiseenkov, A. M.,Filippova, T. M.,Obol'nikova, E. A.,Samokhvalov, G. I.. "C5-HOMOLOGIZATION OF UBIQUINONE-9 AND UBIQUINONE-10 USING SULFUR-CONTAINING SYNTHONS". . p. 594 - 599. Retrieved 2007/10/02.