3-Hydroxydodecanoic acid

Base Information

• Chemical Name: 3-Hydroxydodecanoic acid
• CAS No.: 1883-13-2
• Molecular Formula: C12H24O3
• Molecular Weight: 216.321
• Hs Code.: 2918199090
• European Community (EC) Number: 808-499-4
• DSSTox Substance ID: DTXSID70862773
• Nikkaji Number: J111.042J
• Wikidata: Q27073732
• Pharos Ligand ID: 83URCPRB3FDM
• Metabolomics Workbench ID: 1313
• ChEMBL ID: CHEMBL4288936
• Mol file: 1883-13-2.mol

Synonyms:3-hydroxydodecanoic acid;3-hydroxydodecanoic acid, (+-)-isomer;3-hydroxydodecanoic acid, (R)-isomer;3-hydroxydodecanoic acid, (S)-isomer;3-hydroxydodecanoic acid, ion (1-);3-hydroxydodecanoic acid, ion (1-), (+-)-isomer;3-hydroxydodecanoic acid, monosilver (1+) salt, (R)-isomer;beta-hydroxylauric acid

Chemical Property of 3-Hydroxydodecanoic acid

Chemical Property:

• Appearance/Colour: Solid
• Vapor Pressure: 5.86E-10mmHg at 25°C
• Melting Point: 70-70.5 °C
• Refractive Index: 1.576
• Boiling Point: 348 °C at 760 mmHg
• PKA: 4.38±0.10(Predicted)
• Flash Point: 178.4 °C
• PSA: 57.53000
• Density: 0.987 g/cm³
• LogP: 2.96270
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 216.17254462
• Heavy Atom Count: 15
• Complexity: 157

Purity/Quality:

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

3-HydroxylauricAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCC(CC(=O)O)O
• Uses: 3-hydroxydodecanoic 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 olefins from β-hydroxy carboxylic acids. 3-Hydroxylauric 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 olefins from β-hydroxy carboxylic acids.

Technology Process of 3-Hydroxydodecanoic acid

There total 19 articles about 3-Hydroxydodecanoic 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: 90.0%

3-hydroxydodecanoic acid ethyl ester (183613-15-2) → 3-hydroxydodecanoic acid (1883-13-2,53941-38-1)

Guidance literature:

3-hydroxydodecanoic acid ethyl ester; With lithium hydroxide; water; In tetrahydrofuran; at 20 ℃; for 12h;

With hydrogenchloride; water; In tetrahydrofuran;

Reference yield: 86.0%

β-hydroxydodecanoic acid methyl ester (72864-23-4,85464-97-7) → 3-hydroxydodecanoic acid (1883-13-2,53941-38-1)

Guidance literature:

With methanol; potassium hydroxide; In hexane; at 50 - 60 ℃; for 0.5h;

DOI:10.1055/s-0034-1379479

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

upstream raw materials:

methyl 3-oxododecanoate

caprinaldehyde

ethyl bromoacetate

bromoacetic acid tert-butyl ester

Downstream raw materials:

2-methyldecanal

β-hydroxydodecanoic acid methyl ester

benzyl 3-hydroxydodecanoate

N-(3-hydroxy-dodecanoyl)-L-homoserine lactone

Refernces

• 1、 Jovanovic, Milos,Radivojevic, Jelena,O'Connor, Kevin,Blagojevic, Stevan,Begovic, Biljana,Lukic, Vera,Nikodinovic-Runic, Jasmina,Savic, Vladimir. "Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans". supporting information. p. 209 - 217. Retrieved 2019/03/23.
• 2、 Galleano, Iacopo,Schiedel, Matthias,Jung, Manfred,Madsen, Andreas S.,Olsen, Christian A.. "A Continuous, Fluorogenic Sirtuin 2 Deacylase Assay: Substrate Screening and Inhibitor Evaluation". supporting information. p. 1021 - 1031. Retrieved 2016/02/23.