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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:
Molecular Weight:
166.17
Beilstein:
2209791
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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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.[1]
  • 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.[2]
  • Phenylmethyl-1,3-dioxolane-2,4-dione by condensation reaction with trichloromethyl chloroformate (diphosgene) in the presence of activated charcoal.[3]

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

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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
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
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)
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)
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

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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