3-Hydroxytetradecanoic acid

Base Information

• Chemical Name: 3-Hydroxytetradecanoic acid
• CAS No.: 1961-72-4
• Molecular Formula: C14H28 O3
• Molecular Weight: 244.375
• Hs Code.: 2918199090
• UNII: FL8S7F2JJQ
• DSSTox Substance ID: DTXSID20941380
• Nikkaji Number: J61.335E
• Wikidata: Q27158359
• Metabolomics Workbench ID: 1381
• ChEMBL ID: CHEMBL4456892
• Mol file: 1961-72-4.mol

Synonyms:3-hydroxymyristic acid;3-hydroxytetradecanoic acid;beta-hydroxymyristic acid;beta-hydroxymyristic acid, (R)-isomer

Chemical Property of 3-Hydroxytetradecanoic acid

Chemical Property:

• Vapor Pressure: 3.16E-07mmHg at 25°C
• Melting Point: 80 °C
• Boiling Point: 376.9°Cat760mmHg
• PKA: 4.38±0.10(Predicted)
• Flash Point: 195.9°C
• PSA: 57.53000
• Density: 0.969g/cm³
• LogP: 3.74290
• Storage Temp.: 2-8°C
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 12
• Exact Mass: 244.20384475
• Heavy Atom Count: 17
• Complexity: 180

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-HydroxytetradecanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC(CC(=O)O)O
• Uses: 3-Hydroxytetradecanoic Acid is used in the preparation of liposomes coated with N-acylated molecular-weight. Also used in the synthesis of pseudomycin side-chain analogs. Also used in the study of Lipid A, a major constituent of the lipopolysaccharides, which are responsible for the toxicity of gram negative bacteria.

Technology Process of 3-Hydroxytetradecanoic acid

There total 20 articles about 3-Hydroxytetradecanoic 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:

lipopolysaccharide from Sinorhizobium fredii HH103, rkpA → 3-hydroxytetradecanoic acid (1961-72-4,3422-31-9) + 3-hydroxydodecanoic acid (1883-13-2,53941-38-1) + 3-hydroxytridecanoic acid (32602-69-0) + 3-hydroxypentadecanoic acid (32602-70-3) + β-hydroxypalmitic acid (928-17-6,2398-34-7,20595-04-4,83780-74-9) + 3-hydroxy-heptadecanoic acid (40165-89-7) + 3-hydroxyoctadecanoic acid (17773-30-7) + 3-hydroxy-nonadecanoic acid (40165-90-0) + 27-hydroxy-octacosanoic acid (121822-56-8) + 29-hydroxytriacontanoic acid

Guidance literature:

lipopolysaccharide from Sinorhizobium fredii HH₁₀₃, rkpA; With hydrogenchloride; water; at 100 ℃; for 4h;

With water; sodium hydroxide; at 100 ℃; for 0.5h;

DOI:10.1074/jbc.ra120.013393

Reference yield:

lipopolysaccharide from Sinorhizobium fredii HH103, rkpM → 3-hydroxytetradecanoic acid (1961-72-4,3422-31-9) + 3-hydroxydodecanoic acid (1883-13-2,53941-38-1) + 3-hydroxytridecanoic acid (32602-69-0) + 3-hydroxypentadecanoic acid (32602-70-3) + β-hydroxypalmitic acid (928-17-6,2398-34-7,20595-04-4,83780-74-9) + 3-hydroxy-heptadecanoic acid (40165-89-7) + 3-hydroxyoctadecanoic acid (17773-30-7) + 3-hydroxy-nonadecanoic acid (40165-90-0) + 27-hydroxy-octacosanoic acid (121822-56-8) + 29-hydroxytriacontanoic acid

Guidance literature:

lipopolysaccharide from Sinorhizobium fredii HH₁₀₃, rkpM; With hydrogenchloride; water; at 100 ℃; for 4h;

With water; sodium hydroxide; at 100 ℃; for 0.5h;

DOI:10.1074/jbc.ra120.013393

Reference yield:

n-tetradecanoic acid (544-63-8) → lauric acid (143-07-7) + 2-hydroxytetradecanoic acid (2507-55-3) + 3-hydroxytetradecanoic acid (1961-72-4,3422-31-9) + tridecanoic acid (638-53-9)

Guidance literature:

With cytochrome P₄₅₀ peroxygenase CYP₁₅₂B₁; In aq. phosphate buffer; at 37 ℃; for 0.0166667h; pH=7; Enzymatic reaction;

DOI:10.1039/c7cy02263h

upstream raw materials:

methyl 3-oxotetradecanoate

Dodecanal

ethyl bromoacetate

cycl-isopropylidene malonate

Downstream raw materials:

tridecan-2-one

2-methyldodecanal

(R)-3-hydroxytetradecanoic acid

(+/-)-3-hydroxytetradecanoic acid methyl ester

Refernces

• 1、 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.
• 2、 Zachos, Ioannis,Ga?meyer, Sarah Katharina,Bauer, Daniel,Sieber, Volker,Hollmann, Frank,Kourist, Robert. "Photobiocatalytic decarboxylation for olefin synthesis". supporting information. p. 1918 - 1921. Retrieved 2015/02/05.