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Methyl mandelate

$64

  • Brand : BIOFRON

  • Catalogue Number : BN-O1271

  • Specification : 98%(HPLC)

  • CAS number : 4358-87-6

  • Formula : C9H10O3

  • Molecular Weight : 166.17

  • PUBCHEM ID : 78066

  • Volume : 20mg

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Catalogue Number

BN-O1271

Analysis Method

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

166.17

Appearance

Botanical Source

Structure Type

Category

SMILES

COC(=O)C(C1=CC=CC=C1)O

Synonyms

Hydroxy-phenyl-acetic acid methyl ; ester/3-methoxycarbonyl-2H-cycloheptafuran-2-one/Methyl 2-hydroxy-2-phenylacetate/Mandelic acid methyl ester/2-methoxycarbonyl-2H-cycloheptafuran-2-one/methyl-2-hydroxy-2-phenylacetate/(±)-methyl mandelate/methyl mandelate/methyl-2H-cycloheptafuran-2-one-3-carboxylate/QYR&VO1/hydroxyphenylacetic acid methyl ester/Methyl DL-Mandelate/Methyl hydroxy(phenyl)acetate/DL-Mandelic Acid Methyl Ester/Benzeneacetic acid, α-hydroxy-, methyl ester

IUPAC Name

methyl 2-hydroxy-2-phenylacetate

Density

1.2±0.1 g/cm3

Solubility

Flash Point

113.1±14.5 °C

Boiling Point

258.1±0.0 °C at 760 mmHg

Melting Point

54-58ºC

InChl

InChl Key

ITATYELQCJRCCK-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:4358-87-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

23247722

Abstract

Vibrational absorption (VA) and vibrational circular dichroism (VCD) spectra of methyl mandelate, a prototype chiral molecule, in a series of organic solvents, namely methanol (MeOH-d(4)), dimethyl sulfoxide (DMSO-d(6)), and chloroform (CDCl(3)), have been measured in the finger print region from 1800 to 1150 cm(-1). Implicit solvation models in the form of polarizable continuum model and explicit solvation models have been employed independently and simultaneously. The goal is to evaluate their efficiencies in dealing with solvent effects in each solution and to establish a general strategy to adequately account for effects of solvents. Molecular dynamics (MD) simulation and radial distribution function analysis have been performed to aid the construction of the explicit solvation models. Initial geometry searches have been carried out at the B3LYP/6-31G(d) level for the methyl mandelate monomer and its explicit 1 : 1 and 1 : 2 solute-solvent hydrogen-bonded complexes. B3LYP/cc-pVTZ has been used for all the final geometry optimizations, the vibrational frequency, VA and VCD intensity, and optical rotation dispersion (ORD) calculations. The results show that inclusion of solvent explicitly and implicitly at the same time has significant impacts on the appearance of the VA and VCD spectra, and is crucial for reliable spectral assignments when solvents are capable of hydrogen-bonding interactions with solutes. When no strong solvent-solute hydrogen-bonding interactions in the case of chloroform are expected, the gas phase monomer model is adequate for spectral interpretation, while inclusion of implicit solvation improves the frequency agreement with experiment. ORD spectra of methyl mandelate in the aforementioned solvents at different concentrations under 5 excitation wavelengths have also been measured. The comparison between the calculated and the experimental ORD spectra supports the conclusions drawn from the VA and VCD investigations.

Title

A comparative VCD study of methyl mandelate in methanol, dimethyl sulfoxide, and chloroform: explicit and implicit solvation models.

Author

Poopari MR1, Dezhahang Z, Xu Y.

Publish date

2013 Feb 7

PMID

26234934

Abstract

Pure rotational spectra of a prototypical prochiral ester, methyl benzoylformate (MBF), and the product of its enantioselective reduction, (R)-(-)-methyl mandelate (MM), were measured in the range of 5-16 GHz, using a cavity-based molecular beam Fourier-transform microwave spectrometer. Potential conformers were located using density functional theory calculations, and one conformer of each species was identified experimentally. The minimum energy conformer of MBF, in which the ester group is in a Z orientation, was observed for the first time. Based on an atoms-in-molecules analysis, MBF contains a weak CH···O=C hydrogen bond between the carbonyl oxygen atom of the ester group and the nearest hydrogen atom of the aromatic ring. In the minimum energy conformer of MM, the ester group is oriented to accommodate a hydrogen bond between the hydrogen atom of the hydroxyl group and the carbonyl oxygen atom (OH···O=C), rather than the sp(3) oxygen atom (OH···O-C). For both species, splittings of the rotational transitions were observed, which are attributed to methyl internal rotation, and the orientations and barrier heights of the methyl tops were determined precisely. The barrier heights for MBF and MM are 4.60(2) and 4.54(3) kJ mol(-1), respectively, which are consistent with values predicted by high-level wavefunction-based calculations. On the basis of an atoms-in-molecules analysis, we propose that destabilization of the sp(3) oxygen atom of the ester group most directly dictates the barrier height.

Title

Rotational spectroscopy of methyl benzoylformate and methyl mandelate: structure and internal dynamics of a model reactant and product of enantioselective reduction.

Author

Schnitzler EG1, Poopari MR, Xu Y, Jager W.

Publish date

2015 Sep 14

PMID

18778042

Abstract

Chiral recognition between alpha hydroxylesters has been studied in jet-cooled complexes of methyl mandelate with methyl lactate. The complex with nonchiral methyl glycolate has also been studied for the sake of comparison. The hydrogen-bond topology of the complexes has been interrogated by means of IR/UV double-resonance spectroscopy in the range of 3 mum. A theoretical approach has been conducted in conjunction with the experimental work to assist in the analysis of the spectra. Owing to the conformational flexibility of the subunits at play, emphasis has been put on the methodology used for the exploration of the potential-energy surface. The hydrogen-bond topology is very similar in the homo- and heterochiral complexes. It involves insertion of the hydroxyl group of methyl mandelate within the intramolecular hydrogen bond of methyl lactate or methyl glycolate, resulting in a five-membered ring. This contrasts with methyl lactate clusters previously studied by FTIR spectroscopy in a filet jet.

Title

Chiral recognition between alpha-hydroxylesters: a double-resonance IR/UV study of the complexes of methyl mandelate with methyl glycolate and methyl lactate.

Author

Le Barbu-Debus K1, Broquier M, Mahjoub A, Zehnacker-Rentien A.

Publish date

2008 Oct 9


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