17773-30-7

Basic information

• Product Name: rac-3-Hydroxyoctadecanoic Acid
• Synonyms: rac-3-Hydroxyoctadecanoic Acid;beta-Hydroxyoctadecanoic acid;beta-Hydroxystearic acid
• CAS NO: 17773-30-7
• Molecular Formula: C₁₈H₃₆O₃
• Molecular Weight: 300.47664
• Mol File: 17773-30-7.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 432.189°C at 760 mmHg
• Flash Point: 229.32°C
• Appearance: /
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: rac-3-Hydroxyoctadecanoic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: rac-3-Hydroxyoctadecanoic Acid(17773-30-7)
• EPA Substance Registry System: rac-3-Hydroxyoctadecanoic Acid(17773-30-7)

Safety Data

• Hazardous Substances Data: 17773-30-7(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C18H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17(19)16-18(20)21/h17,19H,2-16H2,1H3,(H,20,21)/p-1

Upstream product

• 14531-34-1 methyl 3-oxooctadecanoate 
• 629-80-1 n-hexadecylaldehyde 
• 105-36-2 ethyl bromoacetate 
• 94376-77-9 3-bromo-octadecanoic acid 
• 16694-29-4 3-oxooctadecanoic acid 
• 19218-94-1 1-iodotetradecane 
• 75-77-4 chloro-trimethyl-silane 
• 109554-31-6 3-hydroxy-octadecanal 
• 64-17-5 ethanol 
• 62625-23-4 ethyl 3-oxooctadecanoate 
• 4444-84-2 (+/-)-threo-2,3-epoxy-octadecanoic acid 
• 65144-03-8 ethyl 3-hydroxyoctadecanoate 
• 57-11-4 stearic acid 
• 629-90-3 n-heptadecanal 

Downstream Products

• 307557-83-1 C₇₉H₁₁₃ClN₁₂O₂₅ 
• 287922-81-0 phenacyl (R)-3-hydroxyoctadecanoate 
• 19013-36-6 d,l-3-Methoxy-octadecansaeure-methylester 
• 5693-15-2 α-pentadecylsuccinic acid 
• 2420-36-2 (R)-β-hydroxyoctadecanoic acid methyl ester 
• 16694-29-4 3-oxooctadecanoic acid 
• 65144-03-8 ethyl 3-hydroxyoctadecanoate 

Relevant articles and documents

Enzymatic Regio- And Enantioselective C-H Oxyfunctionalization of Fatty Acids

Directed evolution of a P450 hydroxylase (P450BSβ) achieves an engineered enzyme that is able to catalyze C-H oxyfunctionalization of fatty acids (FAs) in a highly regio- and enantioselective fashion (>20:1 Cβ/Cα and > 99% ee in all cases). The biocatalyst displays high reactivity (TON up to 1540), takes inexpensive H2O2 as oxidant, and converts C11-C18 saturated FAs as well as naturally derived unsaturated oleic and linoleic acids to optically pure β-hydroxy FAs. Merging biocatalysis with chemical transformation, we further offer a chemoenzymatic strategy to access valuable FA derivatives bearing 1,3-diol, β-amino, β-lactone, and β-lactam functionalities in either enantiomeric form. Molecular docking studies provide a rationale for the regio- and enantioselectivity of this reaction.

Synthesis of Long-Chain β-Lactones and Their Antibacterial Activities against Pathogenic Mycobacteria

In the quest for new antibacterial agents, a series of novel long- and medium-chain mono- and disubstituted β-lactones was developed. Their activity against three pathogenic mycobacteria—M. abscessus, M. marinum, and M. tuberculosis—was assessed by the resazurin microtiter assay (REMA). Among the 16 β-lactones synthesized, only 3-hexadecyloxetan-2-one (VM005) exhibited promising activity against M. abscessus, whereas most of the β-lactones showed interesting activities against M. marinum, similar to that of the classical antibiotic, isoniazid. Regarding M. tuberculosis, six compounds were found to be active against this mycobacterium, with β-lactone VM008 [trans-(Z)-3-(hexadec-7-en-1-yl)-4-propyloxetan-2-one] being the best growth inhibitor. The promising antibacterial activities of the best compounds in this series suggest that these molecules may serve as leads for the development of much more efficient antimycobacterial agents.