Phenylacetylcarbinol

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ImageFile = LPAC.svg
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IUPACName = ("1R")-1-hydroxy-1-phenyl-propan-2-one
OtherNames = L-PAC
(R)-PAC
Section1 = Chembox Identifiers
CASNo = 1798-60-3
PubChem = 9920426
SMILES = CC(=O) [C@@H] (C1=CC=CC=C1)O
Section2 = Chembox Properties
Formula = C₉H₁₀O₂
MolarMass = 150.174 g/mol
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Phenylacetylcarbinol (abbreviated PAC) is an organic compound used as a chemical precursor in the synthesis of pharmaceuticals such as pseudoephedrine. A chiral molecule, generally only the "laevo" diastereomer of phenylacetylcarbinol (abbreviated variously as L-PAC, R-PAC, LPAC, or "(R)"-PAC) is used, because L-PAC transforms to "(R)"-"(-)"-pseudoephedrine—the commercially used isomer of pseudoephedrine—when processed in a reductive amination reaction.

Production

L-PAC is widely synthesized by fermentation of benzaldehyde and dextrose. In this process, colonies of yeast (in particular, strains such as Candida utilis, Torulaspora delbrueckii, or Saccharomyces cerevisiae) are cultivated and added to a broth of water, dextrose, and the enzyme pyruvate decarboxylase in a vat. The yeast is left to grow for a period of time, after which the benzaldehyde is introduced into the broth. The yeast then ferments the benzaldehyde into L-PAC. [ [http://ariic.library.unsw.edu.au/unsw/adt-NUN20051014-005230/ LEKSAWASDI, N. "Kinetics and Modelling of Enzymatic Process for R-phenylacetylcarbinol (PAC) Production". University of New South Wales; Sydney, Australia. August, 2004; pp. 8-15.] ]

The majority of L-PAC is generated in pharmaceutical plants in India, as an intermediate precursor in the production of pseudoephedrine.

References