7622-22-2

Usage

Uses

Used in Fragrance Industry:
BENZYL (R)-(+)-2-HYDROXY-3-PHENYLPROPIONATE is used as a fragrance ingredient for its sweet, floral scent, contributing to the creation of perfumes, soaps, and other personal care products. Its aromatic qualities enhance the sensory experience of these products, making them more appealing to consumers.
Used in Flavor Industry:
In the flavor industry, BENZYL (R)-(+)-2-HYDROXY-3-PHENYLPROPIONATE serves as a flavoring agent in food products. Its ability to impart a pleasant taste adds value to various food items, improving their overall flavor profile and consumer acceptance.
Used in Pharmaceutical Industry:
BENZYL (R)-(+)-2-HYDROXY-3-PHENYLPROPIONATE has potential applications in the pharmaceutical sector, particularly in the development of new drugs and medications. Its chemical properties may offer unique opportunities for medicinal innovation, contributing to advancements in healthcare and therapeutic solutions.

InChI:InChI=1/C16H16O3/c17-15(11-13-7-3-1-4-8-13)16(18)19-12-14-9-5-2-6-10-14/h1-10,15,17H,11-12H2/t15-/m1/s1

Upstream product

• 100-39-0 benzyl bromide 
• 828-01-3 D-phenyllactic acid 
• 100-51-6 benzyl alcohol 
• 93434-59-4 3-Phenyl-2(S)-hydroxypropionic acid benzyl ester 
• 673-06-3 D-(R)-phenylalanine 

Downstream Products

• 153052-70-1 benzyl N-Boc-N-methyl-L-leucyl-3-phenyl-D-lactate 
• 212117-43-6 (S)-2-{(R)-3-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyloxy]-2-oxo-azepan-1-yl}-4-methyl-pentanoic acid (R)-1-benzyloxycarbonyl-2-phenyl-ethyl ester 
• 342418-56-8 (R)-1-Phenyl-3-vinyl-pent-4-ene-2,3-diol 
• 188908-75-0 (S)-2-{(R)-3-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyloxy]-2-oxo-pyrrolidin-1-yl}-4-methyl-pentanoic acid (R)-1-benzyloxycarbonyl-2-phenyl-ethyl ester 
• 858972-94-8 2-[2-(tert-butoxycarbonylmethylamino)acetoxy]-3-phenylpropionic acid benzyl ester 
• 903881-52-7 benzyl (S)-2-(3'-bromophenoxy)-3-phenylpropanoate 
• 882069-81-0 (S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propionic acid benzyl ester 
• 950493-29-5 benzyl (2S)-2-{[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}-3-phenylpropanoate 

Relevant academic research and scientific papers

Selective Monovalent Galectin-8 Ligands Based on 3-Lactoylgalactoside

Galectin-8 has gained attention as a potential new pharmacological target for the treatment of various diseases, including cancer, inflammation, and disorders associated with bone mass reduction. To that end, new molecular probes are needed in order to better understand its role and its functions. Herein we aimed to improve the affinity and target selectivity of a recently published galectin-8 ligand, 3-O-[1-carboxyethyl]-β-d-galactopyranoside, by introducing modifications at positions 1 and 3 of the galactose. Affinity data measured by fluorescence polarization show that the most potent compound reached a KD of 12 μM. Furthermore, reasonable selectivity versus other galectins was achieved, making the highlighted compound a promising lead for the development of new selective and potent ligands for galectin-8 as molecular probes to examine the protein's role in cell-based and in vivo studies.

ENDOPARASITIC DEPSIPEPTIDES

The present invention provides cyclic depsipeptides of Formula (1), stereoisomers thereof, and veterinary acceptable salts thereof (1) wherein each of R1, R2, R3, R4, L1, and L2, are as defined herein. The present invention also contemplates compositions and methods of treatment as an endoparasiticide with a Formula (1) compound.

ENDOPARASITIC DEPSIPEPTIDES

The present invention provides cyclic depsipeptides of Formula (1), stereoisomers thereof, and veterinary acceptable salts thereof wherein each of R1, R2, R3, R4, L1, and L2 are as defined herein. The present invention also contemplates compositions, methods of treatment, and uses as a medicament to treat an animal for an endoparasitic infection with a Formula (1 ) compound.

Total synthesis of the cyclic depsipeptide YM-280193, a platelet aggregation inhibitor

The first total synthesis of YM-280193, a cyclic depsipeptide that inhibits the ADP-induced aggregation of human platelets, is described. The monomer and dipeptide fragments were prepared using conventional chemistry and subsequently assembled by Fmoc-solid-phase peptide synthesis (Fmoc-SPPS). A late-stage novel bis-alkylation-elimination of cysteine on-resin was employed to introduce the unnatural N-methyldehydroalanine moiety. The final step involved execution of a key macrolactamization reaction between the hindered unnatural N,O-dimethylthreonine and ?2-hydroxyleucine residues.

Organocatalytic synthesis of optically active aryllactic acid derivatives from β-ketosulfoxides

The organocatalytic synthesis of new α-acyloxy-3-arylpropionic thioesters has been accomplished providing some enantioenriched important aryllactic acid derivatives in good yield and enantioselectivities.

Synthesis, characterization and activity of new phosphonate dipeptides as potential inhibitors of VanX

VanX, a Zn(II)-dependent D-ala-D-ala dipeptidase, is essential for vancomycin resistance in Enterococcus faecium. The enzymatic activity of VanX was previously found to be inhibited competitively by 2-{[(1-aminoethyl) (hydroxy) phosphoryl]oxy} propanoic acid (1B). Here we report the synthesis and characterization of seven phosphonate dipeptide analogs of D-ala-D-ala with various substituent, the activity evaluation indicated that six of these phosphonate analogs inhibit VanX with IC50 of 0.48-8.21 mM. These data revealed a structure-activity relationship which is that the large substituent group on β-carbon resulted in low binding affinity of the phonphonate analog to VanX. This information will be helpful to guide the design and synthesis of the tightly-binding inhibitors for VanX.

Characterization of binding affinities in a chromatographic system by suspended state HR/MAS NMR spectroscopy

In the current work a racemate of (R)-and (S)-benzylmandelate was separated with a stereoselective polysaccharide-based chiral stationary phase by HPLC. To elucidate the occurring chiral molecular recognition processes in the heterogeneous system used, NMR spectroscopy was chosen under high resolution/magic angle spinning (HR/MAS) NMR conditions in the suspended state. Therefore, and as a proof of concept, a combination of several NMR methods such as spin - lattice relaxation time (T1) measurements (T1), the saturation transfer difference, and the 2D experiment of the transferred nuclear overhauser enhancement spectroscopy technique were applied. With HR/MAS NMR it is feasible to combine NMR and chromatography to achieve further insights into the separation process. Copyright

Total synthesis of hirsutellide A

The total synthesis of hirsutellide A 1 was described. The linear hexadepsipeptide precursor 2 was synthesized in 45% yield from N-Boc-Me-Gly by three coupling reactions with DCC, HATU and BOP-Cl, respectively. Macrocyclization was successfully performed on the fully deprotected amino acid 14 with BOP-Cl in 15% yield and with FDDP in 22% yield.

Synthesis of the key precursor of Hirsutellide A

Hexadepsipeptide 2, the precursor of Hirsutellide A (1), was synthesized in an overall yield of 45% from N-Boc-Me-Gly via three coupling reactions using dicyclohexylcarbodiimide (DCC), O-(7-azabenzotriazol-1-yl)-N,N,N′, N′-tetramethyluronium hexafluorophosphate (HATU) and bis(2-oxo-3- oxazolidinyl)phosphinic chloride (BOP-Cl), respectively.

Synthesis of brassinosteroids of varying acyl side chains and evaluation of their brassinolide-like activity

Brassinosteroids containing various side chain moieties were synthesized and their activity was determined as the reciprocal logarithm of the ED 50 (50% effective dose per plant in moles) in the rice lamina inclination assay using synergist indole-3-acetic acid (IAA). The introduction of a hydroxyl group in the α-position to the carbonyl group of the ester structure significantly enhanced the activity. 2α,3α-Dihydroxy- 17β-[(2R,3S)-2-hydroxy-3-methylpentanoyl]oxy-B-homo-7-oxa-5α- androstan-6-one showed the highest activity, for which the pED50 was determined to be 10.5 under synergistic conditions with IAA. Under identical conditions, the pED50 values of brassinolide and castasterone were determined to be 13.6 and 12.3 respectively. With respect to the α-carbon of the acyl moiety, the R-form was 10 times more potent than the corresponding S-form. Substituting the terminal structure (Et) of the side chain to that of the most potent compound, brassinolide (i-Pr), did not increase the activity.