4617-33-8

Usage

Uses

Used in Chemical Synthesis:
15-Hydroxypentadecanoic acid is used as a reagent for the synthesis of macrocyclic lactone musk compounds such as exaltolide and phoracantholide I, which are important in the fragrance industry due to their unique scent properties.
Used in Analytical Chemistry:
As an internal standard in the quantification of the formation of 11-hydroxylauric acid by gas chromatography, 15-Hydroxypentadecanoic acid helps ensure accurate and reliable results in chemical analyses.
Used in Radiolabeled Compound Synthesis:
In the synthesis of [16-14C]16DCA (Dicarboxylic acid) by a one-carbon elongation procedure at C15, 15-Hydroxypentadecanoic acid serves as a crucial intermediate, enabling the production of radiolabeled compounds for various research applications.
Used in Mass Spectrometry:
15-Hydroxypentadecanoic acid is used as an internal standard for the normalization of intensities in the mass spectra of plant cutin polymer, aiding in the accurate identification and quantification of various components within the polymer.
Used in Catalyst Research:
It may be used in the synthesis of 5-pentadecanolide on dealuminated HY zeolite, contributing to the study and development of new catalysts for chemical reactions.
Used in Pharmaceutical Research:
15-Hydroxypentadecanoic acid can also be utilized in the synthesis of fatty acid analogs of podophyllotoxin, which has potential applications in the development of new drugs and therapies.

InChI:InChI=1/C15H30O3/c16-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15(17)18/h16H,1-14H2,(H,17,18)/p-1

Upstream product

• 76529-42-5 methyl 15-hydroxypentadecanoate 
• 116754-58-6 13-bromo-1-tridecylalcohol 
• 18424-76-5 dimethyl malonate sodium salt 
• 626-86-8 adipinic acid monoethyl ester 
• 54894-30-3 11-acetoxyundecanoic acid 
• 66003-64-3 ethyl 15-acetoxypentadecanoate 
• 38223-29-9 12-oxo-15-pentadecanolide 
• 1902-00-7 15-chloropentadecanoic acid 
• 92857-49-3 15-Hydroxy-pentadecen-⁽²⁾-saeure 
• 92857-51-7 cis-15-Hydroxy-pentadecen-⁽²⁾-saeure 
• 57-57-8 β-Propiolactone 
• 106-02-5 pentadecanolide 
• 18270-60-5 15-hydroxy-pentadecanoic acid hydrazide 
• 6996-92-5 benzeneseleninic acid 

Downstream Products

• 76529-42-5 methyl 15-hydroxypentadecanoate 
• 106-02-5 pentadecanolide 
• 1460-18-0 pentadecanedioic acid 
• 97462-95-8 15-(Toluene-4-sulfonyloxy)-pentadecanoic acid 
• 77172-46-4 isopropyl 15-hydroxypentadecanoate 
• 659-76-7 1,17-dioxa-cyclodotriacontane-2,18-dione 
• 79134-83-1 1,17,33-trioxacyclooctatetracontane-2,18,34-trione 
• 78651-85-1 1-carboxytetradecyl 15-hydroxytetradecanoate 
• 16697-83-9 N-methyl-N-tosylacetamide 
• 67400-04-8 Δ¹³-tetradecenol 
• 905302-64-9 tert-butyl 15-bromopentadecanoate 
• 7370-42-5 γ-pentadecalactone 
• 10411-39-9 methyl 15(Z)-octadecenoate 
• 99208-90-9 15-hexadecyn-1-oic acid 

Relevant academic research and scientific papers

ONE-STEP SYNTHESIS OF ω-HYDROXYCARBOXYLIC ACIDS BY THE REACTION OF ω-METALOXYLATED GRIGNARD REAGENTS WITH β-PROPIOLACTONES

ω-Metaloxylated Grignard reagents reacted with β-propiolactones chemo- and regioselectively in the presence of Li2CuCI4 to afford ω-hydroxycarboxylic acids in high yields.

Practical syntheses of some insect sex pheromones, 10- and 12-alken-1-ol acetates

Some insect sex pheromones 10-dodecen-1-ol acetates 5a(Z/E) and 12-tetradecen-1-ol acetates 5b(Z/E) have been synthesized from cis-13-docosenoic acid 1a and cis-15-tetracosenoic acid 1b via the isomerization of key intermediates 11-dodecen-1-ol acetate 4a and 13-tetradodecen-1-ol acetate 4b.

Novel insights into oxidation of fatty acids and fatty alcohols by cytochrome P450 monooxygenase CYP4B1

CYP4B1 is an enigmatic mammalian cytochrome P450 monooxygenase acting at the interface between xenobiotic and endobiotic metabolism. A prominent CYP4B1 substrate is the furan pro-toxin 4-ipomeanol (IPO). Our recent investigation on metabolism of IPO related compounds that maintain the furan functionality of IPO while replacing its alcohol group with alkyl chains of varying structure and length revealed that, in addition to cytotoxic reactive metabolite formation (resulting from furan activation) non-cytotoxic ω-hydroxylation at the alkyl chain can also occur. We hypothesized that substrate reorientations may happen in the active site of CYP4B1. These findings prompted us to re-investigate oxidation of unsaturated fatty acids and fatty alcohols with C9–C16 carbon chain length by CYP4B1. Strikingly, we found that besides the previously reported ω- and ω-1-hydroxylations, CYP4B1 is also capable of α-, β-, γ-, and δ-fatty acid hydroxylation. In contrast, fatty alcohols of the same chain length are exclusively hydroxylated at ω, ω-1, and ω-2 positions. Docking results for the corresponding CYP4B1-substrate complexes revealed that fatty acids can adopt U-shaped bonding conformations, such that carbon atoms in both arms may approach the heme-iron. Quantum chemical estimates of activation energies of the hydrogen radical abstraction by the reactive compound 1 as well as electron densities of the substrate orbitals led to the conclusion that fatty acid and fatty alcohol oxidations by CYP4B1 are kinetically controlled reactions.

Design, synthesis and pharmacology of aortic-selective acyl-CoA: Cholesterol O-acyltransferase (ACAT/SOAT) inhibitors

We describe our molecular design of aortic-selective acyl-coenzyme A:cholesterol O-acyltransferase (ACAT, also abbreviated as SOAT) inhibitors, their structure–activity relationships (SARs) and their pharmacokinetic (PK) and pharmacological profiles. The connection of two weak ligands—N-(2,6-diisopropylphenyl)acetamide (50% inhibitory concentration [IC50] = 8.6 μM) and 2-(methylthio)benzo[d]oxazole (IC50 = 31 μM)—via a linker comprising a 6 methylene group chains yielded a highly potent molecule, 9-(benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)nonanamide (3h) that exhibited high potency (IC50 = 0.004 μM) toward aortic ACAT. This head-to-tail design made it possible to markedly enhance the activity to 2150- to 7750-fold and to discriminate the isoform-selectivity based on the double-induced fit mechanism. At doses of 1 and 3 mg/kg, 3h significantly decreased the lipid-accumulation areas in the aortic arch to 74 and 69%, respectively without reducing the plasma total cholesterol level in high fat- and cholesterol-fed F1B hamsters. Here, we demonstrate the antiatherosclerotic effect of 3h in vivo via its direct action on aortic ACAT and its powerful modulator of cholesterol level. This molecule is a potential therapeutic agent for the treatment of diseases involving ACAT-1 overexpression.

Mild and chemoselective lactone ring-opening with (TMS)ONa. Mechanistic studies and application to sweroside derivatives

Mild and chemoselective opening of lactones with sodium trimethylsilanolate in high yields and aprotic solvents is described. Kinetic studies demonstrate that the BAc2 mechanistic pathway is followed. Nucleophilic attack of silanolate onto the carbonyl of the lactone moiety is the rate-determining step. NaOH present as an impurity accelerates the reaction. The method was further applied to the base-sensitive and stable lactones derived from highly functionalized iridoid derivatives.

A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues

The cyclic peptide core of the antifungal and antibiotic cyclic depsipeptide LI-F04a was synthesised by using a modified Yamaguchi macrolactonization approach. Alternative methods of macrolactonization (e.g., Corey-Nicolaou) resulted in significant epimerization of the C-terminal amino acid during the cyclization reaction. The D-stereochemistry of the alanine residue in the naturally occurring cyclic peptide may be required for the antifungal activity of this natural product.

Indium tribromide catalyzed cross-Claisen condensation between carboxylic acids and ketene silyl acetals using alkoxyhydrosilanes

Acylations achieved: The title reaction between carboxylic acids and ketene silyl acetals has been accomplished (see scheme). The additive, (MeO) 3SiH, is believed to play an important role in the promotion of the condensation reaction. This reaction system was compatible with a diverse range of functional groups, including alkenes, alkynes, chlorides, alcohols, esters, and nitro groups. Copyright

Enzymatic aminolysis of lactones in aqueous miniemulsion: Catalysis through a novel pathway

Lipase-catalyzed aminolysis of lactones under aqueous conditions usually leads to the hydrolysis of the ester bond with only a minor content of the corresponding amide. However, the aminolysis of pentadecanolide (PD) and hexadecanolide (HD), respectively, with oleylamine (OA) in aqueous miniemulsion under optimized conditions (temperature, concentration of enzyme, reaction time) yields >90% amide. Kinetic investigations performed with OA and PD reveal that the lipase catalyzes a novel reaction pathway, i.e., the hydrolysis of a lactone followed by the amidation requiring 30. min and 8 days reaction time, respectively. The demands of a high amount of lipase as well as the long reaction time are caused by the low reactivity of the carboxylic group and the formation of salt with the amine. Similar reactions were performed with PD and other amines such as dodecyl, decyl, octyl, benzyl and hexyl amine resulting the analogous amide compounds.

Synthesis of ω-hydroxy carboxylic acids and α,ωdimethyl ketones using α,ω-diols as alkylating agents

"Chemical equation presented" Synthesis of ω-hydroxy carboxylic acids and α,ω-dimethyl diketones was successfully achieved by using α,ω-diols as alkylating agents under the influence of an iridium catalyst. For example, the alkylation of butyl cyanoacetate with 1,13-tridecanediol in the presence of [IrCl(cod)]2 or [rrCl(coe) 2]2 gave rise to butyl 2-cyano-15-hydroxypentadecanoate in good yield which is easily converted to cyclopentadecanolide (CPDL). In addition, the alkylation of acetone with 1,10-decanediol in the presence of [IrCl(cod)]2 and KOH resulted in an important muscone precursor, 2,15-hexadecanedione (HDDO), in good yield.

Simple preparation of highly pure monomeric ω-hydroxycarboxylic acids

Highly pure monomeric ω-hydroxycarboxylic acids (HCAs) with ≥C6 are prepared from their corresponding lactones or alkyl ω-hydroxycarboxylates through saponification followed by H 2SO4 acidification and treatment at 35-40 °C/8-12 mbar or by freeze-drying. The HCA is being formed through its sodium or potassium salt and is obtained in 80-85% yield with >99.5% purity, uncontaminated with dimers. This simple procedure excludes chromatographic purification.