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P7251

Sigma-Aldrich

3-Phenyllactic acid

≥98%

Synonym(s):

α-Hydroxyhydrocinnamic acid, β-Phenyllactic acid, 2-Hydroxy-3-phenylpropionic acid

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About This Item

Linear Formula:
C6H5CH2CH(OH)COOH
CAS Number:
828-01-3
Molecular Weight:
166.17
Beilstein:
2209791
EC Number:
212-580-4
MDL number:
MFCD00065928
UNSPSC Code:
12352100
PubChem Substance ID:
57654555
NACRES:
NA.22

Assay

≥98%

form

powder

SMILES string

OC(Cc1ccccc1)C(O)=O

InChI

1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)

InChI key

VOXXWSYKYCBWHO-UHFFFAOYSA-N

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Application

3-Phenyllactic acid can be used as a reactant to prepare:
  • O




  • -Acetyl-3-phenyllactic acid by reacting with acetic anhydride in the presence of pyridine.
  • Ethyl 2-oxo-1-(phenylmethyl)-2-[(phenylmethyl)amino]ethyl carbonate by one pot reaction with 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) and aniline.
  • Phenylmethyl-1,3-dioxolane-2,4-dione by condensation reaction with trichloromethyl chloroformate (diphosgene) in the presence of activated charcoal.

Reagent involved in biological studies of:
  • Enantioselectivity of lipase in transesterification
  • Oxidation by glycolate oxidase and catalase

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Dynamic kinetic resolution via dual-function catalysis of modified cinchona alkaloids: Asymmetric synthesis of α-hydroxy carboxylic acids
Tang Liang and Deng Li
Journal of the American Chemical Society, 124(12), 2870-2871 (2002)
Tiago de Melo Nazareth et al.
Toxins, 12(1) (2020-01-08)
Fungal spoilage is an important issue for the food industry, leading to food sensory defects, food waste, economic losses and public health concern through the production of mycotoxins. Concomitantly, the search for safer natural products has gained importance since consumers
Design and structure-activity relationships of potent and selective inhibitors of undecaprenyl pyrophosphate synthase (UPPS): tetramic, tetronic acids and dihydropyridin-2-ones
Peukert S, et al.
Bioorganic & medicinal chemistry letters, 18(6), 1840-1844 (2008)
Mattia Quattrini et al.
International journal of food microbiology, 302, 8-14 (2018-09-18)
Fungal spoilage of bread remains an unsolved issue in bread making. This work aims to identify alternative strategies to conventional preservatives in order to prevent or delay fungal spoilage of bread. The minimum inhibitory concentration (MIC) of bacterial metabolites and
Use of 2-ethoxy-1-(ethoxycarbonyl)-1, 2-dihydroquinoline as a convenient reagent for the selective protection or derivatization of 2-hydroxycarboxylic acids
Hyun Myung Ho, et al.
Tetrahedron Letters, 40(17), 3435-3438 (1999)
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Chromatograms

application for HPLC

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