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R-ALA vs S-ALA

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R-ALA Home | R-ALA vs S-ALAIngredients & Directions | References

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All ALA Is Not The Same

There are two forms of alpha lipoic acid. R-ALA is the form found naturally occurring within the body and is the biologically active form of alpha lipoic acid.  S-ALA is the unnatural, synthetic byproduct created during the production of alpha lipoic acid.

S-ALA is not sold by itself as isn’t very effective, but you typically get S-ALA when you purchase ALA. The standard ALA you buy from nutrition stores is in reality a 50/50 mixture of S-ALA & R-ALA.

Most companies don’t go through the complicated and expensive process required to purify and remove the synthetic S-ALA from their products. Be aware that unless the bottle specifically states 100% R-ALA, you are only getting a 50/50 blend.



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It is important for you to know that R-ALA has been shown to be up to 12 times as effective as S-ALA. There have been many studies, doctors and researchers who have stated how much more effective R-ALA is.

The Benefits of R-Linoic Acid
  • R-Lipoic acid is the only form of lipoic acid that your body synthesizes and can safely metabolize. (7)
  • R-Lipoic acid is the only form of lipoic acid that is proven to significantly reduce inflammation, an underlying cause of aging. (5)
  • R-Lipoic acid is the only form of lipoic acid that is proven to significantly increase your cellular and mitochondrial antioxidant activity for preventing mitochondrial decay. This effectively attenuates the reported increase in oxidative stress with aging. (8)
  • R-Lipoic acid is the only form of lipoic acid that is proven to improve memory, reduce brain damage, reverse cognitive dysfunction, and protect the brain from neurodegeneration associated with aging. (8,9,22)
  • R-Lipoic acid is the only form of lipoic acid that is been proven to significantly increase insulin sensitivity, enhance glucose transport, increase metabolic rate and reduce the gain in body fat from aging. (10,11)
  • R-Lipoic acid is the only form of lipoic acid that is proven to protect body fats against oxidative damage, chelate harmful metals and reverse stress damage in your heart. (12,13)
  • R-Lipoic acid is the only form of Lipoic that is proven to significantly increase or maintain levels of other antioxidants including Coenzyme Q10, vitamin C, vitamin E and glutathione. (14,15)
  • R-Lipoic acid is the only form of Lipoic acid that is proven to expand total life span. (17)



The problems of S-Lipoic Acid:

  • S-Lipoic acid produces different biological actions than R-Lipoic Acid that may be undesirable. (16-18)
  • S-Lipoic acid produces limited beneficial effects since it cannot bind with key enzymes. (19)
  • S-Lipoic acid is less effective than R-Lipoic Acid as an antioxidant. (20)
  • At high concentrations, S-Lipoic acid inhibits mitochondria metabolism and the antioxidant activity of R-lipoic acid (21)
  • S-Lipoic acid is metabolized in the outer cell membrane. This may interfere with R-Lipoic acid’s ability to penetrate the inner mitochondrial membrane and energy production. (22)

R-Lipoic acid costs slightly more per unit than alpha-Lipoic acid. But it may be 12 times stronger than regular alpha-Lipoic acid at reducing inflammation, a primary cause of aging. And it is free of the problems from the S-form.

What Researchers Say

Dr. Tory Hagen, in Mitochondrial Decay in Aging.
“We’re finding – and others are, too – that the R(+)-form – the natural form – is much more powerful than the racemic mixture ... Hopefully ... companies are going to be producing on more of a clinical scale the R(+)-form of lipoic acid, because we’re finding very significant effects using this, as opposed to the racemic mixture.”

Dr. Ryan Streeper and colleagues, in The American Journal of Physiology.
“We have presented in this study new information indicating that this enhancement of glucose metabolism is sterospecific, with the R(+)-enantiomer being much more effective than the S(-)- enantiomer.”

Dr. Bruce Ames, in Strategies for Engineered Negligible Senescence. “Lipoic acid sold in a health food store is a synthetic mixture, a racemic mixture. And R[+]- is the natural form and S[-]- is an unnatural one ... And in our hands R[+]-works and S[-]- doesn’t.”

Dr. Lester Packer and colleagues, in Free Radical Biology and Medicine.
“R[+]-LA [that is, R(+)-lipoic acid], and not a racemic mixture of R[+]-and S[-]- LA, should be considered a choice for therapeutic applications.”

Dr. Guido Zimmer and colleagues, in Methods in Enzymoogy.
“The S[-]-enantiomer … part of the racemate, which is present as about a 50% impurity, needs to be eliminated.”


References
1. Packer L, Witt EH, Tritschler HJ. Alpha-lipoic acid as a biological antioxidant. Free Rad Biol Med 1995;19:227-250
2. Ou P, Tritschler HJ, Wolff SP. Thioctic (lipoic) acid: a therapeutic metal-chelating antioxidant? Biochem Pharmacol 1995; 50:123-126.
3. Hagen et al, "(R)-alpha-Lipoic acid-supplemented Old Rats Have Improved Mitochondrial Function, Decreased Oxidative Damage, and Increased Metabolic Rate," FASEB J 1999 13:411-418
4. Freisleben HJ, Neeb A, Lehr F, Ackermann H. Influence of selegiline and lipoic acid on the life expectancy of immunosuppressed mice. Arzneimittelforschung 1997 Jun; 47(6): 776-80
5. Ulrich H, Weischer CH, et al. Pharmaceutical composition containing R-.alpha.-lipoic acid or S-.alpha.-lipoic acid as active ingredient. US Patent 5,728,735, 1998.
6. Hagen et al, op. cit.
7. Suh JH, et al, Oxidative stress in the aging rat heart is reversed by dietary supplementation with (R)-(alpha)-lipoic acid. FASEB J 2001 Mar; 15(3): 700-6
8. Liu J, Head E, Gharib AM, et al, Memory loss in old rats is associated with brain mitochondrial decay and RNA/DNA oxidation: partial reversal by feeding acetyl-L-carnitine and/or R-alpha -lipoic acid. Proc Natl Acad Sci U S A 2002 Feb 19; 99(4): 2356-61
9. Hager K, Marahrens A, Kenklies M, et al, Alpha-lipoic acid as a new treatment option for Azheimer type dementia. Arch Gerontology Geriatric 2001 Jun; 32(3): 275-282
10. Jacob S, Rues P, Hermann R. Oral administration of RAC-alpha-lipoic acid modulates insulin sensitivity in patients with type-2 diabetes mellitus: a placebo-controlled pilot trial. Free Rad Biol Med 1999 Aug;27(3-4):309-14
11. Moines H, Trios O, Park YC, Chow KJ, Packer L R-alpha-Lipoic Acid Action on Cell Redox Status, the Insulin Receptor, and Glucose Uptake in 3T3-L1 Adipocytes. . Arch Biochem Biophys 2002 Jan 15; 397(2): 384-91.
12. Suh JH, Shigeno ET, Morrow JD, Cox B, Rocha AE, Frei B, Hagen TM. Oxidative stress in the aging rat heart is reversed by dietary supplementation with (R)-(alpha)-lipoic acid. FASEB J 2001 Mar; 15(3): 700-6
13. Androne L, Gavan NA, Veresiu IA, Orasan R, In vivo effect of lipoic acid on lipid peroxidation in patients with diabetic neuropathy. In Vivo 2000 Mar-Apr; 14(2): 327-30
14. Suh JH, Shigeno ET, et al, Oxidative stress in the aging rat heart is reversed by dietary supplementation with (R)-(alpha)-lipoic acid. FASEB J 2001 Mar; 15(3): 700-615. Lykkesfeldt J, et al, Ames BN. Age-associated decline in ascorbic acid concentration, recycling, and biosynthesis in rat hepatocytes--reversal with (R)-alpha-lipoic acid supplementation. FASEB J 1998 Sep; 12(12): 1183-9
16. Streeper RS, Henriksen EJ, et al, Tritschler HJ. Differential effects of lipoic acid stereoisomers on glucose metabolism in insulin-resistant skeletal muscle. Am J Physiol 1997 Jul; 273(1 Pt 1): E185-91
17. Freisleben HJ, Neeb A, Lehr F, Ackermann H. Influence of selegiline and lipoic acid on the life expectancy of immunosuppressed mice Arzneimittelforschung 1997 Jun; 47(6): 776-80
18. Haramaki N, Han D, Handelman GJ, Tritschler HJ, Packer L. Cytosolic and mitochondrial systems for NADH- and NADPH-dependent reduction of alpha-lipoic acid Free Radic Biol Med 1997; 22(3): 535-42
19. Maitra I, Serbinova E, et al. Stereospecific effects of R-lipoic acid on buthionine sulfoximine-induced cataract formation in newborn rats. Biochem Biophys Res commun 1996; 221:422-429.
20. Streeper RS, Henriksen EJ, et al, Differential effects of lipoic acid stereoisomers on glucose metabolism in insulin-resistant skeletal muscle. Am J Physiol 1997 Jul; 273(1 Pt 1): E185-91
21. M.S. Patel, et al, Stereospecific effects of lipoic acids on mammalian pyruvate dehydrogenase complex
22. Packer, L; Tritschler, H; Wessel K, Neuroprotection by the metabolic Antioxidant alpha Lipoic Acid. 1997 Free Rad Biol Med 22, Nos 1/2, 359-378

 


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