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Aldrich-M59203; Methyl nicotinate 0.99; CAS No.: 93-60-7; Synonyms: Nicotinic acid methyl ester; Linear Formula: C7H7NO2; Empirical Formula: C7H7NO2; find related products, papers, technical documents, MSDS & more at Sigma-Aldrich.

Methyl nicotinate 99 93-60-7

Methyl nicotinate

Helical and zigzag coordination polymeric chains derived from di-3-pyridyl ketone and silver (I) salts

Topical antirheumatic agents as hydroxyl radical scavengers

A facile synthesis of ? -sesbanine via &#947;-addition of ketene silyl acetal with quaternized methyl nicotinate

A general synthesis of 5-arylnicotinates

Synthesis of 3, 5-diacyl-4-phenyl-1, 4-dihydropyridines

Stability of methylnicotinate in aqueous solution as utilized in the'niacin patch test'

The use of laser Doppler perfusion imaging (LDPI) and laser speckle perfusion imaging (LSPI) is well known in the noninvasive investigation of microcirculatory blood flow. This work compares the two techniques with the recently developed tissue viability (TiVi) imaging system, which is proposed as a useful tool to quantify red blood cell concentration in microcirculation. Three systems are evaluated with common skin tests such as the use of vasodilating and vasoconstricting drugs (methlynicotinate and clobetasol, respectively) and a reactive hyperaemia maneuver (using a sphygmomanometer). The devices investigated are the laser Doppler line scanner (LDLS), the laser speckle perfusion imager (FLPI)-both from Moor Instruments (Axminster, United Kingdom)-and the TiVi imaging system (WheelsBridge AB, Linkoping, Sweden). Both imaging and point scanning by the devices are used to quantify the provoked reactions. Perfusion images of vasodilatation and vasoconstriction are acquired with both LDLS and FLPI, while TiVi images are acquired with the TiVi imager. Time acquisitions of an averaged region of interest are acquired for temporal studies such as the reactive hyperaemia. In contrast to the change in perfusion over time with pressure, the TiVi imager shows a different response due its measurement of blood concentration rather than perfusion. The responses can be explained by physiological understanding. Although the three devices sample different compartments of tissue, and output essentially different variables, comparisons can be seen between the three systems. The LDLS system proves to be suited to measurement of perfusion in deeper vessels, while FLPI and TiVi showed sensitivity to more superficial nutritional supply. LDLS and FLPI are insensitive to the action of the vasoconstrictor, while TiVi shows the clear boundaries of the reaction. Assessment of the resolution, penetration depth, and acquisition rate of each instrument show complimentary features that should be taken into account when choosing a system for a particular clinical measurement.

Comparison of instruments for investigation of microcirculatory blood flow and red blood cell concentration.

Skin antioxidant network protects cells against oxidative injury and prevents the production of oxidation products. When oxidative stress overwhelms the skin antioxidant capacity, the subsequent modification of the cellular redox apparatus leads to an alteration of cell homeostasis leading to degenerative processes. In the dermocosmetic field, the topical application of antioxidants is often suggested as a possible strategy to prevent and modulate oxidative skin damages. Continuing our studies addressed to set-up new bio-engineering protocols for the claim substantiation of antioxidant cosmetic products, we have developed a new non-invasive methodology for the evaluation of antioxidants cosmetics ingredients and finished products. The effects of a pre-treatment on forearm skin with an antioxidant ingredient were investigated on 15 volunteers, in a double-blind randomised fashion. A non-invasive method was devised that comprises the collection of forehead SC layers of the pre-treated area and control and the next evaluation of skin antioxidant capacity (IAC-S) by a luminescence-based method. The results showed that the antioxidant preparation was able to increase, to a statistically significant extent (P<0.01), the IAC-S in comparison with the control area. The data were confirmed (P<0.05) by comparison with a method, previously developed by us, based on DermAnalyzer. In view of the simplicity and reliability of the method here presented, this new technique is proposed as a possible tool for the routine evaluation of in vivo efficacy of antioxidant functional ingredients and finished products.

A non-invasive method for the in vivo determination of skin antioxidant capacity (IAC-S).

Topical application of nicotinic acid results in erythema, and in some cases oedema of the skin, supporting a strong relationship between niacin sensitivity and prostaglandin D2. The aim of this study was to examine the inter-rater and intra-rater reliability of a 12-min niacin sensitivity test in healthy adults. Three raters assessed the skin reaction of 12 volunteers, over 3-min intervals across four niacin concentrations (0.1, 0.01, 0.001, and 0.0001), and over six sessions. Inter-rater reliability estimates ranged from 0.85 to 0.97 for the total niacin sensitivity score. Similar inter-rater reliability estimates were found for niacin sensitivity ratings by concentration and time. Intra-rater reliability estimates ranged from 0.63 to 0.93 for the total niacin sensitivity score. These data indicate that the 12-min topical niacin sensitivity test has excellent reliability.

The topical niacin sensitivity test: an inter- and intra-rater reliability study in healthy controls.

This study aimed to investigate the effect of a novel kind of immune-stimulating complexes (ISCOMs) on human skin penetration of model compounds in vitro to evaluate their potential as a delivery system, ultimately for transcutaneous vaccination. Special focus was on elucidating the mechanisms of penetration. Preparation of ISCOMs was done by dialysis and subsequent purification in a sucrose density gradient. The penetration pathways of acridine-labeled ISCOMs were visualized using confocal laser scanning microscopy (CLSM). Transmission electron microscopy (TEM) was used to evaluate the ultrastructural changes in the skin after application of the ISCOMs with or without hydration. Transcutaneous permeation of the model compound, methyl nicotinate, was evaluated in diffusion cells. The prepared ISCOMs were 42-52 nm in diameter as evaluated by dynamic light scattering with zeta potentials of -33 to -26.1 mV. TEM investigations verified the presence of ISCOM structures. Penetration of acridine into skin was greatly increased by incorporation into ISCOMs as visualized by CLSM. Permeation of methyl nicotinate was enhanced in the presence of ISCOMs. Ultrastructural changes of the intercellular space in the stratum corneum after exposure of ISCOMs were observed on micrographs, especially for hydrated skin. In conclusion, cutaneous application of ISCOMs leads to increased penetration of hydrophobic model compounds through human stratum corneum and thus shows potential as a transcutaneous delivery system. The increased penetration seems to be reflected by a change in the intercellular space between the corneocytes, and the effect is most likely caused by the components of the ISCOMs rather than intact ISCOMs.

In vitro cutaneous application of ISCOMs on human skin enhances delivery of hydrophobic model compounds through the stratum corneum.

Recent figures show that tuberculosis (TB) is advancing and killing more than two million people annually, yet no breakthrough in rapid diagnostics is in sight. Volatile metabolites of Mycobacterium tuberculosis (MTB) may provide just that. It is well established that MTB produces nicotinic acid in vitro. We have converted the free acid into methyl nicotinate and detected statistically significant differences in the breath of smear positive patients compared with healthy (smear negative) subjects.

The scent of Mycobacterium tuberculosis--part II breath.

Excess substrate has been identified as an unintended spectator ligand affecting enantioselectivity in the [2 + 2 + 2] cycloaddition of alkenyl isocyanates with tolanes. Replacement of excess substrate with an exogenous additive affords products with consistent and higher ee's. The increase in enantioselectivity is the result of a change in composition of a proposed rhodium(III) intermediate on the catalytic cycle. The net result is a rational probe of a short-lived rhodium(III) intermediate and gives insight that may have applications in many rhodium-catalyzed reactions.

Excess substrate is a spectator ligand in a rhodium-catalyzed asymmetric [2 + 2 + 2] cycloaddition of alkenyl isocyanates with tolanes.

Wu-Zhu-Yu, is an extract prepared from the small berry fruit of Evodia rutaecarpa and is reported to have anti-inflammatory and anti-nociceptic activity. Methyl nicotinate (MN) is known to induce the release of PGD(2) resulting in localized erythema within 30 min after topical application to human skin. The purpose of this study was to determine if a defined biomimetic mixture of components of Evodia fruit extract inhibit inflammation in human cells and skin. In order to control the potency of the test article, we prepared a defined biomimetic mixture of synthetic and natural forms of the active components of Evodia fruit extract, containing rutaecarpine, dehydroevodiamine, and evodin. This was tested for anti-inflammatory activity in UVB-irradiated cultured cells and in the MN model of micro-inflammation in human skin. This Evodia biomimetic mixture was a potent inhibitor of UVB-induced PGE(2) released by keratinocytes in culture. We found that MN also induces release of nitric oxide from cultured keratinocytes and microvascular endothelial cells. Twice daily application of 0.1-1% Evodia biomimetic mixture for 2 weeks significantly inhibited erythema after a MN challenge. A single application of 1% Evodia biomimetic mixture also significantly inhibited MN-induced erythema when applied at 60 min before, or within 5 min after MN exposure. The Evodia biomimetic mixture was significantly more effective at inhibiting erythema than bisabolol, the active component of chamomile. These results demonstrate that compounds found in E. rutaecarpa (including the indole quinazoline alkaloids) have powerful anti-inflammatory activity when applied topically to human skin.

Anti-inflammatory activity in skin by biomimetic of Evodia rutaecarpa extract from traditional Chinese medicine.

Identification and quantification of methyl nicotinate in rice (Oryza sativa L.) by gas chromatography-mass spectrometry

Schizophrenia is associated with a blunted flush response to niacin. Since niacin-induced skin flushing is mediated by vasodilators derived from arachidonic acid (AA), we tested whether the blunted flush response to niacin is a marker of AA deficiency. Eight concentrations of methylnicotinate were applied to the forearms of 20 adults with schizophrenia and 20 controls. Laser Doppler measurement of blood flow responses was used to derive values for niacin sensitivity (defined as the concentration eliciting half-maximal response, i.e., EC(50) value) and efficacy (defined as the maximal evoked blood flow response). RBC membrane fatty acids were analyzed by gas chromatography. Niacin sensitivity and efficacy were reduced in schizophrenia. In the control group, there was significant correlation between AA levels and niacin sensitivity as well as a trend toward correlation between AA levels and niacin efficacy. In contrast, neither sensitivity nor efficacy of niacin correlated with AA levels in schizophrenia. An expected correlation between the levels of AA and its elongation product (adrenic acid) was absent in schizophrenia. Adrenic acid levels correlated with niacin efficacy in schizophrenia. The schizophrenia-associated niacin response abnormality involves both diminished sensitivity and reduced efficacy. The lack of expected correlation between levels of AA and adrenic acid suggests homeostatic imbalance within the n-6 polyunsaturated fatty acid (PUFA) pathway in schizophrenia. Though AA levels were unrelated to measures of niacin response in schizophrenia, the correlation between adrenic acid and niacin efficacy in schizophrenia suggests relevance of the n-6 PUFA pathway to the blunted niacin response.

Niacin sensitivity and the arachidonic acid pathway in schizophrenia.

The proboscis extension reflex in honeybees was evaluated for detection of tuberculosis. Restrained bees were tested with methyl phenylacetate, methyl p-anisate, and methyl nicotinate, previously identified from Mycobacterium tuberculosis cultures, to determine honeybee capacity for signature volatile detection. Methyl p-anisate and methyl phenylacetate were detectable over eight orders of magnitude, and honeybees showed proboscis extension response down to 0.1 pg loading of methyl p-anisate on filter paper. Potential exists for trained honeybees in non-invasive diagnostic tests for TB.

Honeybees Apis mellifera can detect the scent of Mycobacterium tuberculosis.

Worldwide, tuberculosis (TB) kills nearly 2 million people annually, yet rapid diagnosis still relies on a 100-year-old method of sputum staining for acid-fast bacilli. The advent of solid phase micro-extraction and gas chromatography/mass spectrometry makes it possible to systematically investigate whether volatile metabolites from organisms belonging to the genus Mycobacterium can be used as a rapid and highly selective alternative to the traditional diagnostic methods. We have identified four specific compounds (methyl phenylacetate, methyl p-anisate, methyl nicotinate and o-phenylanisole) from Mycobacterium tuberculosis and Mycobacterium bovis cultures grown in vitro that are distinctive volatile markers. These compounds are detectable before the visual appearance of colonies, potentially useful as the basis of a non-invasive diagnostic test for TB and have characteristic odors.

The scent of Mycobacterium tuberculosis.

The development of in silico and in vitro tools to estimate or predict the passive human skin permeation and distribution of new chemical entities, useful in dermal drug delivery, in absorption studies of toxic compounds, and in the cosmetics industry, is presented. In vitro permeation parameters were measured using the artificial membrane PAMPA-skin. The Volsurf approach was then applied to extract pertinent descriptors from molecular interaction fields characterizing the molecular structure of tested compounds. Two useful three-dimensional solvatochromic models able to predict PAMPA permeation parameters directly from the molecular structure were obtained using the partial least squares analysis. The models also provide valuable information to understand the link between physicochemical and structural properties of tested compounds and their interactions with the artificial membrane PAMPA-skin and can be useful to rapidly estimate their permeation through the human skin.

In silico and in vitro filters for the fast estimation of skin permeation and distribution of new chemical entities.

This work was devoted to the search for new artificial membranes allowing a rapid evaluation of passive human skin permeation of compounds with a parallel artificial membrane permeability assay (PAMPA). Effective permeability coefficients (Pe) determined for a set of compounds using the PAMPA technique with isopropyl myristate (IPM) and silicone oil, alone or in mixture, were compared to the corresponding human skin permeability coefficient values (Kp). A good correlation between Pe and Kp was found for compounds tested through a membrane consisting of 70% silicone and 30% IPM. Moreover, positive correlation between the membrane retention of compounds and stratum corneum/water partition coefficients (PSC) was established. These results showed that this new artificial membrane, defined as PAMPA-skin, is able to mimic the main barrier properties of human stratum corneum and can be used for the fast prediction of passive human skin permeability coefficients.

Parallel artificial membrane permeability assay: a new membrane for the fast prediction of passive human skin permeability.

A capillary isoelectric focusing (cIEF) method was developed for the determination of the ionization constants (pKa) of small molecules. Two approaches used to decrease the electroosmotic flow (EOF) were compared: (i) a hydroxypropylcellulose (HPC) coated capillary in aqueous medium and (ii) the addition of glycerol to act as a viscosifying agent. The cIEF method with the glycerol medium was selected, and the ionization constants of 22 basic and 21 acidic compounds, including 15 pharmaceutical drugs, were determined, resulting in pKa values from 3.5 to 7.4 and 6.4 to 9.3, respectively. cIEF offers an interesting alternative to other techniques for pKa determination with low sample consumption, high throughput and low cost.

Methyl nicotinate

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