3-Hydroxyoctadecanoic acid

Base Information

• Chemical Name: 3-Hydroxyoctadecanoic acid
• CAS No.: 17773-30-7
• Molecular Formula: C18H36O3
• Molecular Weight: 300.482
• DSSTox Substance ID: DTXSID501346294
• Nikkaji Number: J297.105D
• Wikidata: Q27122127
• Metabolomics Workbench ID: 2157
• Mol file: 17773-30-7.mol

Synonyms:3-hydroxyoctadecanoate

Chemical Property of 3-Hydroxyoctadecanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 88-90°C
• PSA: 57.53000
• LogP: 5.30330
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 16
• Exact Mass: 300.26644501
• Heavy Atom Count: 21
• Complexity: 229

Purity/Quality:

97% ^*data from raw suppliers

rac-3-Hydroxyoctadecanoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(CC(=O)O)O
• Description: 3-hydroxy Stearic acid is a long-chain saturated fatty acid and intermediate in the production of 3-hydroxy octadecanedioic acid from stearic acid . 3-hydroxy Stearic acid is found in C. pyloridis, a bacteria implicated in the etiology of peptic ulcers. [Matreya, LLC. Catalog No. 1743]
• Uses: rac-3-Hydroxyoctadecanoic acid is a fatty acid found in foodstuffs such as vegetable oils, milk, and dairy products. rac-3-Hydroxyoctadecanoic acid is also used as a chemical marker to identify and confirm the presence of Campylobacter pylori, a gram-negative bacteria that cause duodenal ulcers in humans.

Technology Process of 3-Hydroxyoctadecanoic acid

There total 47 articles about 3-Hydroxyoctadecanoic 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: 99.0%

(R)-β-hydroxyoctadecanoic acid methyl ester (2420-36-2,14531-40-9,14531-45-4,57793-27-8) → (R)-3-hydroxyoctadecanoic acid (14531-43-2,17773-30-7,45261-96-9,14531-50-1)

Guidance literature:

(R)-β-hydroxyoctadecanoic acid methyl ester; With lithium hydroxide monohydrate; In methanol; water; at 20 ℃;

With hydrogenchloride; In methanol; water; at 20 ℃;

DOI:10.1002/chem.201003581

Reference yield: 30.0%

stearic acid (57-11-4) → (R)-3-hydroxyoctadecanoic acid (14531-43-2,17773-30-7,45261-96-9,14531-50-1)

Guidance literature:

With potassium chloride; dihydrogen peroxide; In ethanol; at 20 ℃; for 0.75h; pH=7; stereoselective reaction; Catalytic behavior; Enzymatic reaction;

DOI:10.1021/acscatal.1c03292

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-oxooctadecanoate

ethyl 3-hydroxyoctadecanoate

ethyl 3-oxooctadecanoate

(+/-)-threo-2,3-epoxy-octadecanoic acid

Downstream raw materials:

3-oxooctadecanoic acid

α-pentadecylsuccinic acid

phenacyl (R)-3-hydroxyoctadecanoate

d,l-3-Methoxy-octadecansaeure-methylester

Refernces

• 1、 Kai, Kenji,Murata, Kazuya,Suenaga, Mayuna. "Genome Mining Discovery of Protegenins A-D, Bacterial Polyynes Involved in the Antioomycete and Biocontrol Activities of Pseudomonas protegens". . . Retrieved 2021.
• 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.