METHYL 3-HYDROXYTETRADECANOATE

Base Information

• Chemical Name: METHYL 3-HYDROXYTETRADECANOATE
• CAS No.: 55682-83-2
• Molecular Formula: C15H30 O3
• Molecular Weight: 258.401
• Mol file: 55682-83-2.mol

Synonyms:(?à)-Methyl 3-Hydroxytetradecanoate;Methyl 3-hydroxytetradecanoate

Chemical Property of METHYL 3-HYDROXYTETRADECANOATE

Chemical Property:

• Vapor Pressure: 1.33E-06mmHg at 25°C
• Boiling Point: 359.1°Cat760mmHg
• PKA: 13.91±0.20(Predicted)
• Flash Point: 137.5°C
• PSA: 46.53000
• Density: 0.931g/cm³
• LogP: 3.83130
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

3-Hydroxy Myristic Acid Methyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 3-hydroxy Myristic acid methyl ester is a hydroxylated fatty acid methyl ester that has been found in E. camaldulensis and E. torelliana extracts. It is active against M. tuberculosis (MIC = 49.5 μg/ml) and is non-cytotoxic to Vero cells (IC50 = >100 μM). 3-hydroxy Myristic acid methyl ester is also a volatile compound that contributes to the aroma of red wild strawberries (F. pentaphylla) but is not present in cultivated strawberries (Fragaria x ananassa). [Matreya, LLC. Catalog No. 1736]
• Uses: 3-Hydroxytetradecanoic Acid Methyl Ester is used in the preparation of (S)-3-hydroxytetradecanoic acid and synthesis of unnatural analogs of lipid A containing the (S)-acid.

Technology Process of METHYL 3-HYDROXYTETRADECANOATE

There total 14 articles about METHYL 3-HYDROXYTETRADECANOATE 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: 86.0%

methyl 3-oxotetradecanoate (22348-97-6) → (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃;

DOI:10.1021/jo0162437

Reference yield: 82.0%

Dodecanal (112-54-9) + bromoacetic acid methyl ester (96-32-2) → (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2)

Guidance literature:

With zinc; In benzene; for 2h; Heating;

DOI:10.1080/00397910701263767

Reference yield:

methanol (67-56-1) + lipopolysaccharide from Sinorhizobium fredii HH103, rkpA → 27-hydroxy-octacosanoic acid methyl ester (775341-88-3) + 3-hydroxy-octadecanoic acid methyl ester (2420-36-2) + β-hydroxyhexadecanoic acid methyl ester (51883-36-4) + methyl 3-hydroxytridecanoate (150024-70-7) + Methyl-3-hydroxypentadecanoat (112538-88-2) + β-hydroxydodecanoic acid methyl ester (72864-23-4,85464-97-7) + (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) + Methyl 29-hydroxytriacontanoate + C18H36O3 (112538-92-8) + C20H40O3

Guidance literature:

With hydrogenchloride; In water; at 80 ℃; for 16h;

DOI:10.1074/jbc.ra120.013393

upstream raw materials:

methyl 3-oxotetradecanoate

Dodecanal

bromoacetic acid methyl ester

lauric acid

Downstream raw materials:

methyl (R)-3-hydroxytetradecanoate

(S)-methyl 3-hydroxymyristate

methyl (S)-3-acetoxytetradecanoate

3-hydroxy-tetradecanoic acid benzyloxy-amide

Refernces

• 1、 Hon, Yung-Son,Hsieh, Cheng-Han,Chen, Hsien-Fan. "Dibromomethane as one-carbon source in organic synthesis: Formal total synthesis of (±)-nephrosteranic acid". . p. 1635 - 1651. Retrieved 2007.
• 2、 Di Lorenzo, Flaviana,Speciale, Immacolata,Silipo, Alba,Alías-Villegas, Cynthia,Acosta-Jurado, Sebastián,Rodríguez-Carvajal, Miguel-ángel,Dardanelli, Marta S.,Palmigiano, Angelo,Garozzo, Domenico,Ruiz-Sainz, José-Enrique,Molinaro, Antonio,Vinardell, José-María. "Structure of the unusual Sinorhizobium fredii HH103 lipopolysaccharide and its role in symbiosis". . p. 10969 - 10987. Retrieved 2021/01/07.