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95% Purity L-PAC CAS 1798-60-3

95% Purity L-PAC CAS 1798-60-3

L-PAC CAS 1798-60-3(L-Phenylacetylcarbinol), also known as (R)-1-Hydroxy-1-phenylpropan-2-one, is a pivotal ​chiral pharmaceutical intermediate. It is most renowned as the key precursor in the industrial biosynthesis of ​L-ephedrine and pseudoephedrine, widely used decongestants and stimulants.

  • Name :

    L-PAC
  • CAS No. :

    1798-60-3
  • MF :

    C₉H₁₀O₂
  • MW :

    150.17
  • Purity :

    ≥95%
  • Appearance :

    Typically a pale yellow to colorless viscous liquid or low-melting solid.
  • Storage Condition :

    Should be stored cool, under inert atmosphere, and protected from light.

Chemical Properties

Chemical Name:​​ (R)-1-Hydroxy-1-phenylpropan-2-one

​IUPAC Name:​​ (1R)-1-Hydroxy-1-phenylpropan-2-one

​Synonyms:​​ L-PAC; (R)-PAC; (R)-1-Hydroxy-1-phenyl-2-propanone; L-1-Phenyl-1-hydroxy-2-propanone

​CAS Registry Number:​​ 1798-60-3

​Molecular Formula:​​ C₉H₁₀O₂

​Molecular Weight:​​ 150.17 g/mol

​Chemical Structure:​​ It is an α-hydroxy ketone (acyloin) featuring a phenyl group and a chiral center at the benzylic carbon. The natural microbial product is almost exclusively the ​​(R)-enantiomer, which is crucial for its biological activity and downstream utility.

Appearance:​​ Typically a pale yellow to colorless viscous liquid or low-melting solid.

Boiling Point:​​ Decomposes under atmospheric pressure.

​Optical Rotation:​​ [α]₂₀ᴰ ≈ -50° to -55° (c=1 in ethanol). This high negative optical rotation is a key identifier for the pure (R)-enantiomer.

​Solubility:​​ Soluble in most organic solvents (ethanol, acetone, ethyl acetate, chloroform). Slightly soluble in water.

​Stability:​​ The α-hydroxy ketone structure makes it somewhat sensitive. It can decompose upon heating and is susceptible to oxidation and racemization under strong acidic or basic conditions. Should be stored cool, under inert atmosphere, and protected from light.

 

Biological Activities​

Primary Role:​​ L-PAC itself is not a final therapeutic agent. Its primary significance lies in its ​biological activity as a metabolic intermediate​ in microbial fermentation.

​Biosynthetic Precursor:​​ It is the direct precursor in the microbial pathway for the synthesis of ​L-ephedrine alkaloids.

Enzymatic Activity:​​ It is produced by the action of ​pyruvate decarboxylase (PDC)​, primarily from yeast (e.g., Saccharomyces cerevisiae), on benzaldehyde and pyruvate. This biotransformation is a classic example of a carboligation reaction.

 

Biosynthesis​

L-PAC is almost exclusively produced via ​microbial biotransformation (fermentation)​, which is far more efficient and stereoselective than chemical synthesis for this molecule.

​1.Microorganism:​​ Bakers' yeast (Saccharomyces cerevisiae) is the most common and historical biocatalyst.

2.Process:​​ In a fed-batch or continuous fermentation, ​benzaldehyde​ and a pyruvate source (often pyruvic acid or glucose) are fed to the yeast culture.

​3.Key Enzyme:​​ The enzyme ​Pyruvate Decarboxylase (PDC)​​ catalyzes a two-step reaction: first, decarboxylation of pyruvate to acetaldehyde-thiamine pyrophosphate (TPP) anion; second, carboligation with benzaldehyde to form L-PAC with high enantiomeric excess (>95% (R)).

​4.Product Recovery:​​ L-PAC is recovered from the fermentation broth via solvent extraction.

 

Applications​Applications​

  • #
    Pharmaceutical Industry 
    It is the ​key chiral intermediate​ for the commercial production of:
    ​L-Ephedrine​ and ​Pseudoephedrine: Sympathomimetic amines used as decongestants and bronchodilators in over-the-counter and prescription cold/allergy medications.
    Further chemical or enzymatic reduction of L-PAC yields the corresponding ​phenylpropanolamine​ derivatives.
  • #
    Chiral Building Block
    Used in organic synthesis for the preparation of other fine chemicals and pharmaceuticals requiring this specific chiral phenylacetyl moiety.
     
  • #
    Research
    Serves as a model compound in studying enzymatic carboligation reactions and biocatalysis process optimization.
     

 

 

FAQs

Q1: What is the primary commercial use of L-PAC (CAS 1798-60-3)?​​

A1: Its ​exclusive and major industrial use​ is as the critical biosynthetic precursor in the large-scale fermentation-based production of the decongestants ​L-ephedrine and pseudoephedrine. Over 80% of the world's pseudoephedrine is manufactured via the L-PAC route.

​Q2: Why is the fermentation route preferred over chemical synthesis?​​

A2: Chemical synthesis of L-PAC typically results in a racemic mixture, requiring costly and inefficient resolution. The ​yeast biotransformation process​ is highly ​stereoselective, producing the desired (R)-enantiomer in high optical purity (>95% ee) in a single, efficient step from cheap starting materials (benzaldehyde and glucose).

​Q3: What are the main challenges in L-PAC production?​​

A3:

​Substrate Inhibition/Toxicity:​​ Benzaldehyde is toxic to yeast cells at high concentrations, requiring careful fed-batch control.

​By-product Formation:​​ Yeast metabolism can reduce benzaldehyde to benzyl alcohol or reduce L-PAC to phenylpropanediol, reducing yield. Strain engineering and process optimization are used to minimize this.

​Product Recovery:​​ Efficient extraction from the aqueous fermentation broth is necessary.

​Q4: Can you supply L-PAC, and what specifications are critical?​​

A4: Yes, it is available from specialized fine chemical and chiral intermediate suppliers. Key specifications include:

​Purity​ (by HPLC/GC, typically >98%)

Enantiomeric Excess (e.e.)​​ (Critical, should be >95% (R))

​Optical Rotation​ (as a key physical constant for identity and purity)

​Residual Solvents & Water Content​

​Q5: Are there any regulatory or safety concerns with L-PAC?​​

A5: As a direct precursor to pseudoephedrine/ephedrine (which are monitored/controlled substances in many jurisdictions due to potential misuse), the ​sale and transport of L-PAC are often highly regulated. Suppliers and buyers must comply with strict "know-your-customer" (KYC) procedures, licensing, and regulatory reporting to prevent diversion for illicit drug manufacturing.

​Q6: Is there ongoing research to improve L-PAC production?​​

A6: Yes, significant research focuses on:

Metabolic Engineering:​​ Developing engineered yeast or bacterial strains with higher PDC activity, reduced by-product formation, and greater benzaldehyde tolerance.

​Enzyme Engineering:​​ Creating improved PDC variants with broader substrate specificity or higher catalytic efficiency.

​Process Intensification:​​ Integrating fermentation with in-situ product removal (ISPR) techniques to overcome inhibition and improve productivity.

 

 

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