1961-72-4

Basic information

• Product Name: R-(3)-HYDROXYMYRISTIC ACID
• Synonyms: 3-hydroxy-tetradecanoicaci;beta-hydroxymyristicacid;(R)-(-)-3-HYDROXYTETRADECANOIC ACID;(R)-3-HYDROXYTETRADECONOIC ACID;3-HYDROXYMYRISTIC ACID, (SS-);3-HYDROXYMYRISTIC ACID (BETA-) 96+%;(±)-3-Hydroxyteradecanoic Acid;HYDROXYMYRISTIC ACID, 3-(SG)
• CAS NO: 1961-72-4
• Molecular Formula: C₁₄H₂₈O₃
• Molecular Weight: 244.37
• Mol File: 1961-72-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 80 °C
• Boiling Point: 376.9°Cat760mmHg
• Flash Point: 195.9°C
• Appearance: /
• Density: 0.969g/cm³
• Vapor Pressure: 3.16E-07mmHg at 25°C
• Refractive Index: 1.467
• Storage Temp.: 2-8°C
• PKA: 4.38±0.10(Predicted)
• CAS DataBase Reference: R-(3)-HYDROXYMYRISTIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: R-(3)-HYDROXYMYRISTIC ACID(1961-72-4)
• EPA Substance Registry System: R-(3)-HYDROXYMYRISTIC ACID(1961-72-4)

Safety Data

• RTECS: XB8585000
• Hazardous Substances Data: 1961-72-4(Hazardous Substances Data)

Usage

Uses

3-Hydroxytetradecanoic Acid is used in the preparation of liposomes coated with N-acylated molecular-weight. Also used in the synthesis of pseudomycin side-chain analogs. Also used in the study of Lipid A, a major constituent of the lipopolysaccharides, which are responsible for the toxicity of gram negative bacteria.

Definition

ChEBI: A 3-hydroxy fatty acid that is tetradecanoic (myristic) acid substituted at position 3 by a hydroxy group

InChI:InChI=1/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)

Upstream product

• 22348-97-6 methyl 3-oxotetradecanoate 
• 112-54-9 Dodecanal 
• 105-36-2 ethyl bromoacetate 
• 2033-24-1 cycl-isopropylidene malonate 
• 112-16-3 n-dodecanoyl chloride 
• 55682-83-2 (+/-)-3-hydroxytetradecanoic acid methyl ester 
• 544-63-8 n-tetradecanoic acid 
• 88222-72-4 3-oxomyristic acid 
• 76828-23-4 (4RS)-1-pentadecen-4-ol 
• 176787-14-7 3-Hydroxy-tetradecanal 
• 126679-29-6 Ethyl 3-hydroxytetradecanoate 
• 125749-45-3 (1-carbomethoxyprop-2-yl) bromoacetate 

Downstream Products

• 593-08-8 tridecan-2-one 
• 37596-36-4 2-methyldodecanal 
• 28715-21-1 (R)-3-hydroxytetradecanoic acid 
• 151378-83-5 (S)-3-acetoxytetradecanoic acid 
• 200936-09-0 benzyl 3-hydroxymyristate 
• 55682-83-2 (+/-)-3-hydroxytetradecanoic acid methyl ester 
• 81629-59-6 C₅₈H₇₆N₂O₁₉ 
• 81629-43-8 C₅₉H₇₈N₂O₁₉ 
• 81629-42-7 benzyl 6-O-<2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O--β-D-glucopyranyl>-3-O-benzoyl-2-(DL-3-benzoyloxytetradecanoylamino)-2-deoxy-α-D-glucopyranoside 
• 81629-35-8 benzyl 3-O-benzoyl-2-(DL-3-benzoyloxytetradecanoylamino)-2-deoxy-α-D-glucopyranoside 
• 104640-27-9 benzyl 2-deoxy-4-O-(O,O-diphenylphosphono)-3-O-tetradecanoyl-2-<(3R)-3-tetradecanoyloxytetradecanamido>-β-D-glucopyranoside 
• 104712-61-0 benzyl 2-deoxy-4-O-(O,O-diphenylphosphono)-3-O-tetradecanoyl-2-<(3S)-3-tetradecanoyloxytetradecanamido>-β-D-glucopyranoside 
• 104640-24-6 benzyl 2-deoxy-3-O-tetradecanoyl-2-<(3R)-3-tetradecanoyloxytetradecanamido>-6-O-trityl-β-D-glucopyranoside 
• 104640-25-7 benzyl 2-deoxy-3-O-tetradecanoyl-2-<(3S)-3-tetradecanoyloxytetradecanamido>-6-O-trityl-β-D-glucopyranoside 

Relevant articles and documents

Nanohybrids composed of quantum dots and cytochrome P450 as photocatalysts

(Chemical Equation Presented) Synthesis with light: CdS quantum dots (QDs) generate superoxide and hydroxyl radicals upon UV irradiation in aqueous solution. The radicals are used for activating P450BSβ enzymes attached at the QD surface, effecting the catalytic transformation of myristic acid into α- and β-hydroxymyristic acid (see picture, R = (CH 2)10CH3).

α-Oxidative decarboxylation of fatty acids catalysed by cytochrome P450 peroxygenases yielding shorter-alkyl-chain fatty acids

Cytochrome P450 peroxygenases belonging to the CYP152 family catalyse the oxidation of fatty acids using H2O2. CYP152N1 isolated from Exiguobacterium sp. AT1b exclusively catalyses the α-selective hydroxylation of myristic acid at physiological H2O2 concentration. However, a series of shorter-alkyl-chain fatty acids such as tridecanoic acid were produced from myristic acid by increasing the concentration of H2O2 (1-10 mM). The yield of tridecanoic acid from myristic acid reached 17%. An 18O-labeled oxidant study suggested that CYP152N1 catalysed the overoxidation of α-hydroxymyristic acid to form α-ketomyristic acid, which in turn was spontaneously decomposed by H2O2 to yield tridecanoic acid. Crystal structure analysis of CYP152N1 revealed its high similarity to other CYP152 family enzymes, such as CYP152A1 and CYP152B1. MD simulations of α-hydroxymyristic acid accommodated in CYP152N1 proposed a possible pre-oxidation conformation of α-hydroxymyristic acid for the decarboxylation reaction.

In situ formation of H2O2 for P450 peroxygenases

An in situ H2O2 generation approach to promote P450 peroxygenases catalysis was developed through the use of the nicotinamide cofactor analogue 1-benzyl-1,4-dihydronicotinamide (BNAH) and flavin mononucleotide (FMN). Final productivity could be enhanced due to higher enzyme stability at low H2O2 concentrations. The H2O2 generation represented the rate-limiting step, however it could be easily controlled by varying both FMN and BNAH concentrations. Further characterization can result in an optimized ratio of FMN/BNAH/O2/biocatalyst enabling high reaction rates while minimizing H2O2-related inactivation of the enzyme.