3-hydroxy-3-methylbutyric acid

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Structural formula
Structure of 3-methyl-3-hydroxybutyric acid
General
Surname 3-hydroxy-3-methylbutyric acid
other names
  • 3-methyl-3-hydroxybutanoic acid
  • 3-hydroxyisovaleric acid
  • β-hydroxyisovaleric acid
  • β-hydroxy-β-methylbutanoic acid
  • β-hydroxy-β-methylbutyric acid
  • HMB
Molecular formula C 5 H 10 O 3
Brief description

clear, colorless to slightly yellowish, viscous liquid with an unpleasant odor

External identifiers / databases
CAS number 625-08-1
EC number 626-699-8
ECHA InfoCard 100.128.078
PubChem 69362
Wikidata Q223081
properties
Molar mass 118.13 g · mol -1
Physical state

liquid

density

0.938 g cm −3

Melting point

−80 ° C

boiling point

88 ° C (133 hPa )

solubility

soluble in water and ethanol

Refractive index

1.4415

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

3-Hydroxy-3-methylbutyric acid , often abbreviated to HMB and usually referred to as β-hydroxy-β-methylbutyric acid or β-hydroxy-β-methylbutyrate , is a metabolic product of the essential amino acid L- leucine . The compound has been part of some dietary supplements since the beginning of the 21st century and is believed to have anabolic effects.

effect

About 5 percent of the leucine ingested through food is metabolized into HMB. In the first step, α-ketoisocaproate ( ketoleucine , KIC) is formed from leucine . Part of the KIC is further metabolized in the mitochondria with the help of the enzyme α-keto acid dehydrogenase into isovaleryl coenzyme A. In the cytosol, on the other hand, 3-hydroxy-3-methylbutyric acid (HMB) is formed from KIC with the help of the enzyme α-ketoisocaproate dioxygenase. HMB is therefore a substance that is formed in every healthy body as part of the metabolism.

The muscle proteins consist of about one third of the branched amino acids leucine, L- isoleucine and L- valine . L- leucine is important for maintaining and building muscle tissue. It inhibits the breakdown of muscle proteins and supports protein synthesis in the liver and muscles. The administration of leucine has an anabolic effect.

HMB, the metabolic product of L- leucine, is offered as a dietary supplement and shows, among other things, anabolic, anti-catabolic and lipolytic effects in the human body . HMB is therefore taken by many bodybuilders and strength or endurance athletes in the form of calcium 3-hydroxy-3-methylbutyrate ("Ca-Hmb") in dietary supplements in order to legally increase muscle mass and performance. However, the results of scientific research into the effects of HMB on muscle mass gain are very contradictory. A number of studies show positive effects, while other studies conclude that HMB is ineffective. The knowledge that HMB - compared to placebos - has no effect on well-trained athletes is now largely undisputed . Neither aerobic nor anaerobic performance was any measurable increase in performance through the intake of HMB. In contrast, the administration of HMB in patients with muscle wasting , for example as a result of an AIDS or cancer disease ( tumor cachexia ), appears to have a high probability of positive effects in the affected patients.

HMB is well tolerated even in high doses. No undesirable side effects were found in animal experiments.

Mechanism of action

In model organisms with tumor cachexia, HMB could both reduce the breakdown of proteins and stimulate the build-up of muscle mass. HMB possibly regulates the expression of NF-κB , which is thereby produced to a lesser extent by the cells. The mechanism for building protein mass is via the mTOR receptor, the phosphorylation of which is apparently stimulated by HMB.

literature

  • GJ Slater and D. Jenkins: Beta-hydroxy-beta-methylbutyrate (HMB) supplementation and the promotion of muscle growth and strength. In: Sports Med 30, 2000, pp. 105-116; PMID 10966150 .
  • HL Eley, ST Russell, MJ Tisdale: Mechanism of attenuation of muscle protein degradation induced by tumor necrosis factor-alpha and angiotensin II by beta-hydroxy-beta-methylbutyrate. In: Am J Physiol-Endocrinol Metab 295, 2008, pp. E1417-E1426; PMID 18840762 .
  • HL Eley, ST Russell, MJ Tisdale: Attenuation of depression of muscle protein synthesis induced by lipopolysaccharide, tumor necrosis factor, and angiotensin II by beta-hydroxy-beta-methylbutyrate. In: Am J Physiol-Endocrinol Metab 295, 2008, pp. E1409-E1416; PMID 18854427 .
  • MR Tatrara, E. Sliwa, W. Krupski: Prenatal programming of skeletal development in the offspring: effects of maternal treatment with beta-hydroxy-beta-methylbutyrate (HMB) on femur properties in pigs at slaughter age. In: Bone 40, 2007, pp. 1615-1622; PMID 17433802 .
  • OT Foye, Z. Uni, PR Ferket: Effect of in ovo feeding egg white protein, beta-hydroxy-beta-methylbutyrate, and carbohydrates on glycogen status and neonatal growth of turkeys. In: Poult Sci 85, 2006, pp. 1185-1192; PMID 16830858 .
  • E. Tako, PR Ferket, Z. Uni: Effects of in ovo feeding of carbohydrates and beta-hydroxy-beta-methylbutyrate on the development of chicken intestine. In: Poult Sci 83, 2004, pp. 2023-2028; PMID 15615016 .
  • DS Rowlands and JS Thomson: Effects of beta-hydroxy-beta-methylbutyrate supplementation during resistance training on strength, body composition, and muscle damage in trained and untrained young men: a meta-analysis. In: J Strength Cond Res 23, 2009, pp. 836-846; PMID 19387395 .
  • JS Thomson, PE Watson, DS Rowlands: Effects of nine weeks of beta-hydroxy-beta-methylbutyrate supplementation on strength and body composition in resistance trained men. In: J Strength Cond Res 23, 2009, pp. 827-835; PMID 19387396 .

Individual evidence

  1. ↑ a b c d e f g data sheet β-Hydroxyisovaleric acid, ≥95.0% (T) from Sigma-Aldrich , accessed on December 26, 2019 ( PDF ).
  2. ↑ Data sheet 3-Hydroxy-3-methylbutyric acid, 96% from AlfaAesar, accessed on December 26, 2019 ( PDF )(JavaScript required) .
  3. ↑ M. van Kovering and SL Nissen: Oxidation of leucine and alpha-ketoisocaproate to b-hydroxy-b-methlbutyrate in vivo. In: Am J Physiol Endocrinol Metab 262, 1992, p. 27.
  4. ↑ a b c d G. J. Wilson, JM Wilson, AH Manninen: Effects of beta-hydroxy-beta-methylbutyrate (HMB) on exercise performance and body composition across varying levels of age, sex, and training experience: A review. In: Nutr Metab (Lond) 5, 2008, p. 1; PMID 18173841 ; PMC 2245953 (free full text).
  5. ↑ RC Hider, EB Fern, DR London: Relationship between intracellular amino acids and protein synthesis in the extensor digitorum longus muscle of rats. In: Biochem J 114, 1969, pp. 171-178; PMID 5822066 ; PMC 1184841 (free full text).
  6. ↑ E. Jówko, P. Ostaszewski, M. Jank, J. Sacharuk, A. Zieniewicz, J. Wilczak, S. Nissen: Creatine and β-hydroxy-β-methylbutyrate (HMB) additively increase lean body mass and muscle strength during a weight-training program. In: Nutr 17, 2001, pp. 558-566; doi : 10.1016 / S0899-9007 (01) 00540-8 ; PMID 11448573 .
  7. ^ AE Knitter, L. Panton, JA Rathmacher, A. Petersen, R. Sharp: Effects of β-hydroxy-β-methylbutyrate on muscle damage after a prolonged run. In: J Appl Physiol 89, 2000, pp. 1340-1344. PMID 11007567
  8. ↑ PM Gallagher, JA Carrithers, MP Godard, KE Schulze, SW Trappe: β-hydroxy-β-methylbutyrate ingestion, part I: Effects on strength and fat free mass. In: Med Sci Sports Exerc 32, 2000, pp. 2109-2115. doi : 10.1097 / 00005768-200012000-00022 ; PMID 11128859 .
  9. ↑ DM O'Connor and MJ Crowe: Effects of beta-hydroxy-beta-methylbutyrate and creatine monohydrate supplementation on the aerobic and anaerobic capacity of highly trained athletes. In: J Sports Med Phys Fitness 43, 2003, pp. 64-68; PMID 12629464 .
  10. ↑ T. Palisin and JJ Stacy: Beta-hydroxy-beta-methylbutyrate and its use in athletics. In: Curr Sports Med Rep 4, 2005, pp. 220-223; PMID 16004832 .
  11. ↑ G. Slater, D. Jenkins, P. Logan, H. Lee, M. Vukovich, JA Rathmacher, AG Hahn: Beta-hydroxy-beta-methylbutyrate (HMB) supplementation does not affect changes in strength or body composition during resistance training in trained men. In: Int J Sport Nutr Exerc Metab 11, 2001, pp. 384-396, PMID 11599506 .
  12. ↑ JH Baxter, JL Carlos, J. Thurmond, RN Rehani, J. Bultman, D. Frost: Dietary toxicity of calcium beta-hydroxy-beta-methyl butyrate (CaHMB). In: Food Chem Toxicol 43, 2005, pp. 1731-1741; PMID 16006030 .
  13. ^ MJ Tisdale and SA Beck: Cancer cachexia. In: Int J Pancreatol 7, 1990, pp. 141-150; PMID 2081920 .
  14. ↑ HJ Smith, P. Mukerji, MJ Tisdale: Attenuation of proteasome-induced proteolysis in skeletal muscle by beta-hydroxy-beta-methylbutyrate in cancer-induced muscle loss. In: Cancer Res 65, 2005, pp. 277-283; PMID 15665304 .
  15. ↑ EA Nunes, D. Kuczera, GA Brito, SJ Bonatto, RK Yamazaki, RA Tanhoffer, RC Mund, M. Kryczyk, LC Fernandes: Beta-hydroxy-beta-methylbutyrate supplementation reduces tumor growth and tumor cell proliferation ex vivo and prevents cachexia in Walker 256 tumor-bearing rats by modifying nuclear factor-kappaB expression. In: Nutr Res 28, 2008, pp. 487-493; PMID 19083450 .
  16. ↑ HL Eley, ST Russell, MJ Tisdale: Attenuation of depression of muscle protein synthesis induced by lipopolysaccharide, tumor necrosis factor, and angiotensin II by beta-hydroxy-beta-methylbutyrate. In: Am J Physiol Endocrinol Metab 295, 2008, pp. E1409-1416; PMID 18854427 .