Phenylacetylcarbinol

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Phenylacetylcarbinol
LPAC.svg
Names
IUPAC name
1-hydroxy-1-phenyl-propan-2-one
Other names
l-PAC
(R)-PAC
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.824 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C9H10O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6,9,11H,1H3/t9-/m0/s1 X mark.svgN
    Key: ZBFFNPODXBJBPW-VIFPVBQESA-N X mark.svgN
  • InChI=1/C9H10O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6,9,11H,1H3/t9-/m0/s1
    Key: ZBFFNPODXBJBPW-VIFPVBQEBH
  • CC(=O)[C@@H](C1=CC=CC=C1)O
Properties
C9H10O2
Molar mass 150.177 g·mol−1
AppearanceYellow-green liquid
Density 1.119 g/cm3
Melting point 9–11 °C (48–52 °F; 282–284 K) [1]
Boiling point 253 °C (487 °F; 526 K)
Insoluble
Solubility in other solventsFreely soluble in alcohols, ether, and aromatic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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L-pac produced by biotransformation of benzaldehyde L-pac.jpg
L-pac produced by biotransformation of benzaldehyde

Phenylacetylcarbinol (PAC) is an organic compound that has two enantiomers, one with R- and one with S-configuration. (R)-PAC, which is commonly called l-PAC, is known as a precursor in the synthesis of pharmaceuticals such as ephedrine and pseudoephedrine.

Contents

Nomenclature

(R)-PAC or (R)-(−)-phenylacetylcarbinol is identical to l-PAC, referring to the outdated d/l system. [2] (R)-PAC is the levo-rotating isomer of phenylacetylcarbinol.

The IUPAC name of phenylacetylcarbinol is 1-hydroxy-1-phenylpropan-2-one. Synonyms are 1-hydroxy-1-phenyl-2-propanone and 1-Hydroxy-1-phenylacetone.

Production

(R)-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 (R)-PAC. [3] Boiling point at 12mmHg is 124-125C.

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

There are also biochemical reactions where enzymes such as acetohydroxyacid synthase I from E. coli condense pyruvate and benzaldehyde into R-PAC. Such methods have much higher conversion rates in comparison to the conventional yeast fermentation. [4]

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References

  1. "1-Phenyl-1-hydroxypropan-2-one".
  2. B, Rosche; V, Sandford; M, Breuer; B, Hauer; P, Rogers (2001). "Biotransformation of benzaldehyde into ( R )-phenylacetylcarbinol by filamentous fungi or their extracts". Applied Microbiology and Biotechnology. 57 (3): 309–315. doi:10.1007/s002530100781.
  3. 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. Archived 2006-06-22 at the Wayback Machine
  4. Engel, Stanislav; Vyazmensky, Maria; Berkovich, Dvora; Barak, Ze'ev; Merchuk, Jose; Chipman, David M. (2005). "Column flow reactor using acetohydroxyacid synthase I from Escherichia coli as catalyst in continuous synthesis of R-phenylacetyl carbinol". Biotechnology and Bioengineering. 89 (6): 733–740. doi: 10.1002/bit.20392 . PMID   15685598.