Lot numbers can be found on the outside label of a product:
(S)-2-Acetoxy-3-phenylpropanoic acid
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CAS No. 33173-31-8
- Cat. No. CS-0163395
- Purity≥97%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 33173-31-8
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General Information
- CAS No. 33173-31-8
- Cat. No. CS-0163395
- Purity ≥97%
- MDL No. None
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₁H₁₂O₄
- Molecular Weight 208.21
- Synonym(s) O-ACETYL PHENYL L-LACTIC ACID
- SMILES O=C(O)[C@@H](OC(C)=O)CC1=CC=CC=C1
Description
(S)-2-Acetoxy-3-phenylpropanoic acid features a chiral center at the 2-position, delivering enantioselective reactivity in synthetic transformations. The acetoxy group enables facile ester cleavage under mild conditions, while the phenyl substituent imparts rigidity and enhanced solubility in organic media. This configuration supports efficient incorporation into complex molecular architectures, particularly in medicinal chemistry applications requiring stereocontrol.
Application
(S)-2-Acetoxy-3-phenylpropanoic acid serves as a versatile chiral building block for the synthesis of pharmaceutically relevant β-aryl-α-hydroxy acid motifs. Its acetoxy group enables facile deacetylation or participation in neighboring-group-assisted transformations, while the phenyl and carboxylic acid functionalities support orthogonal functionalization. The stereochemical integrity at C2 ensures reliable asymmetric synthesis outcomes, making it suitable for scale-up in medicinal chemistry campaigns requiring high enantiomeric purity and bench-stable handling.
Synthesis
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Route1
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In-stock
20312-36-1 -
75-36-5 - ~%
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In-stock
33173-31-8
References
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Sengupta, Saumitra; Mondal, Somnath Tetrahedron Letters, 1999 , vol. 40, # 17 p. 3469 - 3470
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Route2
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63-91-2 -
64-19-7
- ~%
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In-stock
33173-31-8
References
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Sleebs, Marianne M.; Scanlon, Denis; Karas, John; Maharani, Rani; Hughes, Andrew B. Journal of Organic Chemistry, 2011 , vol. 76, # 16 p. 6686 - 6693
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Route3
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In-stock
20312-36-1
- ~%
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In-stock
33173-31-8
References
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Merrell Pharmaceuticals Inc. Patent: US5502253 A1, 1996 ;
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H312-H332
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P363-P501
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Quality Control
Computational Chemistry Data
- TPSA 63.6
- LogP 1.2454
- H_Acceptors 3
- H_Donors 1
- Rotatable_Bonds 4
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Key Words
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