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Safety Information

68193

Sigma-Aldrich

Methyl L-3-phenyllactate

≥97.0% (HPLC)

Synonym(s):

Methyl (S)-2-hydroxy-3-phenylpropionate

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About This Item

Empirical Formula (Hill Notation):
C10H12O3
CAS Number:
13673-95-5
Molecular Weight:
180.20
MDL number:
MFCD00038224
UNSPSC Code:
12352108
PubChem Substance ID:
57652130
NACRES:
NA.22

Assay

≥97.0% (HPLC)

optical activity

[α]/D +4.4±0.5°, c = 1% in methanol

mp

40-45 °C (lit.)

functional group

ester
hydroxyl
phenyl

SMILES string

COC(=O)[C@@H](O)Cc1ccccc1

InChI

1S/C10H12O3/c1-13-10(12)9(11)7-8-5-3-2-4-6-8/h2-6,9,11H,7H2,1H3/t9-/m0/s1

InChI key

NMPPJJIBQQCOOI-VIFPVBQESA-N

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Application

Methyl L-3-phenyllactate can be used:
  • As an intermediate in the synthesis of bortezomib analogs as 20S proteasome inhibitors.
  • As a substrate in the amination of the benzylic C-H bonds and the aminated products are further used to prepare β-lactams.
  • As an intermediate in one of the key synthetic steps for the preparation of YM-254890 analog, a selective Gαq/11 inhibitor.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

68193-VAR-F:
68193-25G-F:
68193-BULK-F:
68193-100G-F:
68193-5G-F:

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Certificates of Analysis (COA)

Lot/Batch Number
BCBM8630V
1299674V
1299674
1368259
1068074

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Discovery of novel 20S proteasome inhibitors by rational topology-based scaffold hopping of bortezomib
Xu Y, et al.
Bioorganic & Medicinal Chemistry Letters, 28(12), 2148-2152 (2018)
Toward the selective inhibition of G proteins: total synthesis of a simplified YM-254890 analog
Rensing DT, et al.
Organic Letters, 17(9), 2270-2273 (2015)
Synthesis of Biologically Relevant Compounds by Ruthenium Porphyrin Catalyzed Amination of Benzylic C-H Bonds
Zardi P, et al.
Organometallics, 33(9), 2210-2218 (2014)

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