The Sticky Truth

R-Lipoic acid naturally polymerizes into a glue-like substance

R-Lipoic acid is a highly unstable compound that easily polymerizes into a sticky rubber or glue-like substance if it is not prepared, stored and processed correctly. Even under the best conditions, R-Lipoic acid is extremely unstable. Exposure to air, light, moisture and temperatures slightly above ambient drastically reduces shelf life and increases the formation of this unwanted degradation product that adversely affects bio-availability.

After great effort, we rediscovered the S-S bond is homolytically cleaved by light, heat and acid (water is acidic enough) yielding thiyl radicals that polymerize into a chain of linear disulfides with the carboxyl groups free. The structure of this polymer was known and reported in 1956, in Disulfide Polymers of DL-alpha-Lipoic acid by Richard Thomas and Lester Reed at the Clayton Foundation for Research, The Biochemical Institute and the Dept. of Chemistry at the University of Texas. Only 44 years before us. Time may be better spent in the library than the laboratory.

Specifications for GeroNova’s Bio-Enhanced® R-Lipoic Acid

Only R-Lipoic acid of the highest purity is utilized, after independent analysis confirms the R/S ratio. GeroNova’s typical R-Lipoic acid content >99.4%, SLA=0.2-0.6% with a total ALA content of > 99.8%. The polymer content of our starting material is typically 0.2-0.4%. Opened and refrigerated bottles of finished R-Lipoic acid capsules maintain their potency for 6 months and are still not bio-available. GeroNova’s unique processing into Bio-Enhanced® R-Lipoic acid reduces polymer formation of pure R-Lipoic acid and increases its bio-availability 21 times higher than RLA.

Our first development in solving the polymer problem was the introduction of a unique, low temperature, oxygen free, anhydrous process to insure extremely low polymer content in bulk R-Lipoic acid powder and extended this technology to a proprietary encapsulation process to insure low polymer content in finished capsules.

This development allowed us to consistently produce capsules containing less than 3% polymer. Unfortunately, the stability was still poor in the finished products, as the capsules require refrigeration and have a maximum 6 month shelf life before the polymer content begins to grow quickly in un-refrigerated capsules and powder. One hour in a hot car can cause 100% polymerized RLA.

The rate of dissolution of tablets and capsules can vary greatly between different commercial R-Lipoic acid products. Polymerized RLA/ ALA in capsules and tablets can adversely affect dissolution rates, G.I. absorption and bio-availability even more. Even if tablets or capsules of R-Lipoic acid are not polymeric, there is extensive polymerization on contact in the low pH environment of the stomach.

GeroNova’s Stable Bio-Enhanced® R-lipoic acid

After extensive R & D, GeroNova developed a 80% Na RALA bulk powder. Na RALA is a stable, non-hygroscopic, non-polymeric salt form of R-Lipoic Acid, now produced on an industrial scale. The material is non-hygroscopic and does not require any special handling or refrigeration. The shelf life is at least 3 years, and is used in the manufacture of our Bio-Enhanced® R-Lipoic acid capsules.

The Developing R-Lipoic acid Market

Now that the differences between racemic Alpha Lipoic acid and pure R-Lipoic acid are becoming known, several new companies are attempting to manufacture and introduce R-Lipoic acid products into the market. Many of them are encountering the same problems that GeroNova did initially and that we have subsequently solved. We have discovered that several of these companies have not been able to consistently produce a quality product with high enantiomeric purity. There are wide variations in the R/S ratios and total polymer contents of raw material and finished products.

Information concerning R-Lipoic acid instability has not been passed on to their customers because their products have not been analyzed with state-of-the-art enantioselective HPLC. Frequently, supplement companies or online stores are relying solely on the manufacturer’s C of As or are sending samples to analytical labs whose analysts have limited experience with enantioselective HPLC, which reveals the R/S ratios and total polymer content.

Few supplement companies and even fewer on-line vendors have experience with R-Lipoic acid and are unaware of the myriad problems associated with its encapsulation and stability.

We keep hearing from customers that several otherwise reputable analytical labs claim that it is impossible to test the R/S ratio by HPLC. There are several peer reviewed articles utilizing three different enantioselective assays for quantifying both R-Lipoic acid and S-lipoic in the literature.

Few supplement companies and even fewer on-line vendors have experience with R-Lipoic acid and are unaware of the myriad problems associated with its encapsulation and stability. The heat of friction and exposure to air during normal blending and encapsulation processes are sufficient to initiate the polymerization of both R-Lipoic acid and Alpha-Lipoic acid (although the heat stability is slightly higher for the racemic mixture).

Since the beginning of 2003, dozens of new companies have introduced R-Lipoic acid in finished products with widely varying prices and quality.

Most commercial R-Lipoic acid products don’t meet our standards

GeroNova decided to investigate the polymer content of the various commercial products for R-Lipoic acid and insoluble polymer content. The results were as expected: several of the companies may be deceiving the unknowing public by fraudulently trying to pass off their racemic ALA as RLA.

At best, they are unaware of the problem in their finished products. Three products we analyzed contained no R-Lipoic acid at all; only commercial, inexpensive ALA; some had a mix of ALA and RLA.

Other commercial products did contain R-Lipoic Acid, but had polymer contents ranging from 13-60% per capsule or tablet, or had enantiomeric purities <65%. One product contained a small amount of extensively polymerized R-Lipoic acid mixed with ALA.

GeroNova’s Bio-Enhanced® R-lipoic acid:
The highest quality and most bio-available available

GeroNova routinely sends finished products for independent analysis. Our capsules consistently contain <3% polymer; our liquid K-RALA-10® contains <0.015% polymer; and 0.3% polymer was detected in our bulk Na RALA powder. There is no polymer at all in R-PLUS.

You can rely on GeroNova’s expertise to provide you with the best quality Bio-Enhanced® R-Lipoic acid bulk and finished products available.