3-Hydroxytridecanoic acid

Base Information

• Chemical Name: 3-Hydroxytridecanoic acid
• CAS No.: 32602-69-0
• Molecular Formula: C13H26O3
• Molecular Weight: 230.348
• DSSTox Substance ID: DTXSID10954328
• Nikkaji Number: J297.044I
• Metabolomics Workbench ID: 1378
• Mol file: 32602-69-0.mol

Synonyms:3-hydroxytridecanoic acid

Chemical Property of 3-Hydroxytridecanoic acid

Chemical Property:

• Melting Point: 79 °C(Solv: hexane (110-54-3))
• Boiling Point: 362.6 °C at 760 mmHg
• PKA: 4.38±0.10(Predicted)
• Flash Point: 187.3 °C
• PSA: 57.53000
• Density: 0.977 g/cm³
• LogP: 3.35280
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 230.18819469
• Heavy Atom Count: 16
• Complexity: 169

Purity/Quality:

99%, ^*data from raw suppliers

3-Hydroxytridecanoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCC(CC(=O)O)O
• Uses: 3-Hydroxytridecanoic Acid is used in the study of Lipid A, a major constituent of the lipopolysaccharides, which are responsible for the toxicity of gram negative bacteria. Also used in the synthesis of polyhydroxyalkanoates used in biodegradable thermoplastics and elastomers.

Technology Process of 3-Hydroxytridecanoic acid

There total 2 articles about 3-Hydroxytridecanoic 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:

3-hydroxytridecanoic acid (32602-69-0) → L-(+)-3-Hydroxy-tridecansaeure-benzylester

Guidance literature:

Multi-step reaction with 2 steps

1: (i) H2, Ni catalyst, EtOH, (ii) KOH, (iii) (racemate resolution using (+)-α-methylbenzylamine)

2: Ag₂O / diethyl ether

With silver(l) oxide; In diethyl ether;

Refernces