L-(+)-Tuberculostearic acid

Base Information

• Chemical Name: L-(+)-Tuberculostearic acid
• CAS No.: 133398-13-7
• Molecular Formula: C19H38O2
• Molecular Weight: 298.51
• UNII: P7TR89YR5R
• Metabolomics Workbench ID: 86
• Mol file: 133398-13-7.mol

Synonyms:(10R)-10-methyloctadecanoic acid;10-R-Tuberculostearic acid;P7TR89YR5R;L-(+)-Tuberculostearic acid;Tuberculostearic acid, (R)-;(R)-(-)-Tuberculostearic acid;Octadecanoic acid, 10-methyl-, (10R)-;133398-13-7;UNII-P7TR89YR5R;10R-methyl-octadecanoic acid;SCHEMBL456684;(r)-10-methyloctadecanoic acid;LMFA01020015

Chemical Property of L-(+)-Tuberculostearic acid

Chemical Property:

• XLogP3: 7.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 16
• Exact Mass: 298.287180451
• Heavy Atom Count: 21
• Complexity: 226

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC(C)CCCCCCCCC(=O)O
• Isomeric SMILES: CCCCCCCC[C@@H](C)CCCCCCCCC(=O)O

Technology Process of L-(+)-Tuberculostearic acid

There total 24 articles about L-(+)-Tuberculostearic acid 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: 98.0%

(R)-10-methyloctadecan-1-ol (883878-56-6) → (R)-10-methyloctadecanoic acid (133398-13-7,80508-15-2)

Guidance literature:

With potassium permanganate; tetrabutylammomium bromide; acetic acid; In dichloromethane; water; for 4h; Heating;

DOI:10.1021/jo0625599

Reference yield: 97.0%

ethyl (R)-10-methyloctadecanoate (1082670-89-0,55334-35-5) → (R)-10-methyloctadecanoic acid (133398-13-7,80508-15-2)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; methanol; Reflux;

DOI:10.1039/c7ob01786c

Reference yield: 97.0%

(R)-10-methyloctadec-7-enoic acid → (R)-10-methyloctadecanoic acid (133398-13-7,80508-15-2)

Guidance literature:

With hydrazine hydrate; riboflavin; at 21 ℃; for 24h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c3ob41483c

upstream raw materials:

ethyl (R)-10-methyloctadecanoate

azelaic monomethyl ester

(R)-10-methyloctadecan-1-ol

(R)-4-methyldodecanal

Downstream raw materials:

3-O-benzyl-1-O-((R)-10-methyloctadecanoyl)-sn-glycerol

C₅₅H₉₂NO₁₀P

benzyl (1-O-((R)-10-methylstearyl)-2-O-palmityl-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

C₅₆H₇₆O₁₀

Refernces

• 1、 Burugupalli, Satvika,Almeida, Catarina F.,Smith, Dylan G. M.,Shah, Sayali,Patel, Onisha,Rossjohn, Jamie,Uldrich, Adam P.,Godfrey, Dale I.,Williams, Spencer J.. "α-Glucuronosyl and α-glucosyl diacylglycerides, natural killer T cell-activating lipids from bacteria and fungi". . p. 2161 - 2168. Retrieved 2020/03/10.
• 2、 Fodran, Peter,Minnaard, Adriaan J.. "Catalytic synthesis of enantiopure mixed diacylglycerols-synthesis of a major M. tuberculosis phospholipid and platelet activating factor". . p. 6919 - 6928. Retrieved 2013/10/08.