3422-31-9

Basic information

• Product Name: DL-B-HYDROXYMYRISTIC ACID
• Synonyms: DL-B-HYDROXYMYRISTIC ACID;dl-β-hydroxymyristic acid
• CAS NO: 3422-31-9
• Molecular Formula: C14H28O3
• Molecular Weight: 244.37032
• Mol File: 3422-31-9.mol
• Article Data: 42

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: DL-B-HYDROXYMYRISTIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: DL-B-HYDROXYMYRISTIC ACID(3422-31-9)
• EPA Substance Registry System: DL-B-HYDROXYMYRISTIC ACID(3422-31-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 3422-31-9(Hazardous Substances Data)

Usage

Biochem/physiol Actions

DL-β-Hydroxymyristic acid (3-HTA) is a mixture of D- and L-β-hydroxymyristic acid enantiomers. 3-Hydroxytetradecanoic acids are used to study their roles in biological processes such as oxidative stress, inflammation and insulin resistance. 3-HTA is also used in endotoxin and lipid A research.

Upstream product

• 76828-23-4 (4RS)-1-pentadecen-4-ol 
• 112-54-9 Dodecanal 
• 544-63-8 n-tetradecanoic acid 
• 74794-26-6 (3R)-1-trimethylsilyl-tetradec-1-yn-3-ol 
• 2437-56-1 1-tridecene 
• 123-91-1 1,4-dioxane 
• 76062-97-0 methyl (R)-3-hydroxytetradecanoate 
• 88271-09-4 t-butyl (3RS)-3-hydroxytetradecanoate 
• 958221-98-2 (S)-3-Hydroxy-tetradecanenitrile 
• 22348-97-6 methyl 3-oxotetradecanoate 
• 259799-90-1 (R)-1-cyanotridecan-2-ol 
• 88222-72-4 3-oxomyristic acid 
• 108-05-4 vinyl acetate 
• 1961-72-4 3-hydroxytetradecanoic acid 

Downstream Products

• 81629-34-7 benzyl 2-deoxy-2-(DL-3-hydroxytetradecanoylamino)-4,6-O-isopropylidene-α-D-glucopyranoside 
• 106115-95-1 Benzyl-6-O-<6-O-acetyl-3-O-<α,α-D2>benzyl-2-desoxy-4-O-(diphenoxyphosphoryl)-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosyl>-3,4-di-O-<α,α-D2>benzyl-2-desoxy-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosid 
• 106115-87-1 C₈₅H₁₁₆⁽²⁾H₆N₂O₂₄ 
• 106115-91-7 Benzyl-6-O-acetyl-3-O-<α,α-D2>benzyl-2-desoxy-4-O-(diphenoxyphosphoryl)-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosid 
• 87357-65-1 (3R)-3-hydroxytetradecanoic acid phenacyl ester 
• 91681-56-0 (3R)-3-dodecanoyloxytetradecanoic acid 
• 339316-63-1 (R)-3-Dodecanoyloxy-tetradecanoic acid 2-oxo-2-phenyl-ethyl ester 
• 81629-35-8 benzyl 3-O-benzoyl-2-(DL-3-benzoyloxytetradecanoylamino)-2-deoxy-α-D-glucopyranoside 
• 147353-86-4 (R)-3-(tert-Butyl-dimethyl-silanyloxy)-tetradecanoic acid phenyl ester 

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.

Structure of the unusual Sinorhizobium fredii HH103 lipopolysaccharide and its role in symbiosis

Rhizobia are soil bacteria that form important symbiotic associations with legumes, and rhizobial surface polysaccharides, such as K-antigen polysaccharide (KPS) and lipopolysaccharide (LPS), might be important for symbiosis. Previously, we obtained a mutant of Sinorhizobium fredii HH103, rkpA, that does not produce KPS, a homopolysaccharide of a pseudaminic acid derivative, but whose LPS electrophoretic profile was indistinguishable from that of the WT strain. We also previously demonstrated that the HH103 rkpLMNOPQ operon is responsible for 5-acetamido-3,5,7,9-tetradeoxy-7-(3-hydroxybutyramido)-L-glyc-ero-L-manno-nonulosonic acid [Pse5NAc7(3OHBu)] production and is involved in HH103 KPS and LPS biosynthesis and that an HH103 rkpM mutant cannot produce KPS and displays an altered LPS structure. Here, we analyzed the LPS structure of HH103 rkpA, focusing on the carbohydrate portion, and found that it contains a highly heterogeneous lipid A and a peculiar core oligosaccharide composed of an unusually high number of hexuronic acids containing b-configured Pse5NAc7(3OHBu). This pseudaminic acid derivative, in its a-configuration, was the only structural component of the S. fredii HH103 KPS and, to the best of our knowledge, has never been reported from any other rhizobial LPS. We also show that Pse5NAc7(3OHBu) is the complete or partial epitope for a mAb, NB6-228.22, that can recognize the HH103 LPS, but not those of most of the S. fredii strains tested here. We also show that the LPS from HH103 rkpM is identical to that of HH103 rkpA but devoid of any Pse5NAc7(3OHBu) residues. Notably, this rkpM mutant was severely impaired in symbiosis with its host, Macroptilium atropurpureum.

Bacilotetrins A and B, Anti-Staphylococcal Cyclic-Lipotetrapeptides from a Marine-Derived Bacillus subtilis

LC-MS and NMR spectroscopy guided metabolic profiling and dereplication of a crude extract obtained from the fermentation of a marine-derived bacterium, Bacillus subtilis, followed by chromatographic isolation yielded two new cyclic-lipotetrapeptides, bacilotetrins A (1) and B (2). Based on extensive 1D and 2D NMR and high-resolution ESIMS data analysis, the structures of 1 and 2 were elucidated, revealing the unique structures of these lipopeptides consisting of three leucines and a glutamic acid residue cyclized with a lipophilic 3-hydroxy fatty acid. The absolute stereochemistries at selected stereocenters in 1 and 2 were assigned by chemical derivatization and comparison to literature data. Compounds 1 and 2 exhibited anti-MRSA activity with MIC values of 8 to 32 μg/mL. However, these compounds showed no cytotoxicity when tested against prostate and liver cancer cell lines using the standard SRB assay.