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Key Documents

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:
Molecular Weight:
166.17
Beilstein/REAXYS Number:
2209791
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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C N Sarkissian et al.
Analytical biochemistry, 280(2), 242-249 (2000-05-03)
Phenylketonuria (PKU) (OMIM 261600) is the first Mendelian disease to have an identified chemical cause of impaired cognitive development. The disease is accompanied by hyperphenylalaninemia (HPA) and elevated levels of phenylalanine metabolites (phenylacetate (PAA), phenyllactate (PLA), and phenylpyruvate (PPA)) in
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
S Iijima et al.
The Tohoku journal of experimental medicine, 117(2), 167-178 (1975-10-01)
Wister albino pregnant rats were fed on pellets containing 3.5% L-phenylalanine (Phe) from 10 days before the expected date of birth. The diet was then switched to 7% Phe pellets at the third week after birth. Baby rats were reared
Jessie Bong et al.
Food chemistry, 267, 355-367 (2018-06-24)
New Zealand manuka (Leptospermum scoparium) and kanuka (Kunzea ericoides) honeys contain a unique array of chemical markers useful for chemical fingerprinting. We investigated the presence of 13 potential marker compounds in nectars of the major honey crop species. We confirmed
Helena Lind et al.
FEMS microbiology letters, 271(2), 310-315 (2007-04-26)
Antifungal compounds from cultures of five type strains of dairy propionibacteria, as well as from the cultivation medium, were studied. Cell-free supernatants and medium were fractionated by C(18) solid phase extraction. The aqueous 95% acetonitrile fractions were analyzed by GC-MS

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