β-Hydroxy β-methylbutyric acid

Not to be confused with β-Hydroxybutyric acid.

β-Hydroxy β-methylbutyric acid
Top: β-Hydroxy β-methylbutyric acid
Bottom: β-Hydroxy β-methylbutyrate
Clinical data
Other namesConjugate acid form:
β-hydroxyisovaleric acid
3-hydroxyisovaleric acid
Conjugate base form:
hydroxymethylbutyrate
Routes of
administration		By mouth[1] or nasogastric[2]
ATC code
  • none
Legal status
Legal status
  • US: Dietary supplement
  • UN: Unscheduled
Pharmacokinetic data
MetabolitesHMB-CoA, HMG-CoA, mevalonate, cholesterol, acetyl-CoA, acetoacetate, β-hydroxybutyrate
Onset of actionHMB-FA: 30–60 minutes[1]
HMB-Ca: 1–2 hours[1]
Elimination half-lifeHMB-FA: 3 hours[1]
HMB-Ca: 2.5 hours[1]
ExcretionRenal (10–40% excreted)[1][3]
Identifiers
IUPAC name
  • 3-hydroxy-3-methylbutanoic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.128.078
Chemical and physical data
FormulaC5H10O3
Molar mass118.132 g·mol−1
3D model (JSmol)
Density~1.1 g/cm3 at 20 °C[4]
Melting point−80 °C (−112 °F) (glass)[5]
Boiling point128 °C (262 °F) at 7 mmHg[4][6]
SMILES
  • CC(C)(CC(=O)O)O
InChI
  • InChI=1S/C5H10O3/c1-5(2,8)3-4(6)7/h8H,3H2,1-2H3,(H,6,7) Y
  • Key:AXFYFNCPONWUHW-UHFFFAOYSA-N Y
  (verify)

β-Hydroxy β-methylbutyric acid[note 1] (HMB), otherwise known as its conjugate base, β-hydroxy β-methylbutyrate, is a naturally produced substance in humans that is used as a dietary supplement and as an ingredient in certain medical foods that are intended to promote wound healing and provide nutritional support for people with muscle wasting due to cancer or HIV/AIDS.[sources 1] In healthy adults, supplementation with HMB has been shown to increase exercise-induced gains in muscle size, muscle strength, and lean body mass, reduce skeletal muscle damage from exercise, improve aerobic exercise performance, and expedite recovery from exercise.[sources 2] Medical reviews and meta-analyses indicate that HMB supplementation also helps to preserve or increase lean body mass and muscle strength in individuals experiencing age-related muscle loss.[note 2][11][12][13] HMB produces these effects in part by stimulating the production of proteins and inhibiting the breakdown of proteins in muscle tissue.[11][14][15] No adverse effects from long-term use as a dietary supplement in adults have been found.[16][17][18]

The effects of HMB on human skeletal muscle were first discovered by Steven L. Nissen at Iowa State University in the mid-1990s.[8][19] As of 2018, HMB has not been banned by the National Collegiate Athletic Association, World Anti-Doping Agency, or any other prominent national or international athletic organization.[20][21][22] In 2006, only about 2% of college student athletes in the United States used HMB as a dietary supplement.[23][24] As of 2017, HMB has reportedly found widespread use as an ergogenic supplement among young athletes.[25]

  1. ^ a b c d e f g Wilson JM, Fitschen PJ, Campbell B, Wilson GJ, Zanchi N, Taylor L, Wilborn C, Kalman DS, Stout JR, Hoffman JR, Ziegenfuss TN, Lopez HL, Kreider RB, Smith-Ryan AE, Antonio J (February 2013). "International Society of Sports Nutrition Position Stand: beta-hydroxy-beta-methylbutyrate (HMB)". Journal of the International Society of Sports Nutrition. 10 (1): 6. doi:10.1186/1550-2783-10-6. PMC 3568064. PMID 23374455. The [International Society of Sports Nutrition] has concluded the following. 1. HMB can be used to enhance recovery by attenuating exercise induced skeletal muscle damage in trained and untrained populations. ... 4. Thirty-eight mg·kg·BM−1 daily of HMB has been demonstrated to enhance skeletal muscle hypertrophy, strength, and power in untrained and trained populations when the appropriate exercise prescription is utilized. ... 8. HMB's mechanisms of action include an inhibition and increase of proteolysis and protein synthesis, respectively. 9. Chronic consumption of HMB is safe in both young and old populations.
  2. ^ Cite error: The named reference Ensure and Juven was invoked but never defined (see the help page).
  3. ^ a b "Safety data sheet: 3-Hydroxy-3-methyl butyric acid". Alfa Aesar. 23 March 2005. Archived from the original on 17 September 2016. Retrieved 9 November 2016.
  4. ^ Cite error: The named reference Coffman_1958 was invoked but never defined (see the help page).
  5. ^ "3-OH-isovaleric acid". ChemSpider. Royal Society of Chemistry. 2015. Archived from the original on 11 August 2016. Retrieved 10 August 2016. Experimental Boiling Point: ... 128 °C / 7 mm ...
    Experimental solubility:
    Soluble in water
  6. ^ "beta-Hydroxyisovaleric acid". PubChem Compound. United States National Library of Medicine – National Center for Biotechnology Information. 3 February 2018. Archived from the original on 6 February 2018. Retrieved 6 February 2018. Chemical Names: Beta-Hydroxyisovaleric acid; 3-Hydroxy-3-methylbutanoic acid; ... 3-Hydroxyisovaleric acid; 3-Hydroxy-3-methylbutyric acid
  7. ^ a b Cite error: The named reference Iowa State University was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Medical foods was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference PR Newswire was invoked but never defined (see the help page).
  10. ^ a b Cite error: The named reference Meta-analytic systematic review September 2015 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference August 2017 supplementation review was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference HMB for sarcopenia and sarcopenic obesity – October 2017 review was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference Pimentel 2017 systematic review on HMB was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference Pharmacology of HMB-FA in humans in vivo was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference Molecular Aspects of Medicine 2016 review was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference Systematic review December 2013 was invoked but never defined (see the help page).
  17. ^ Cite error: The named reference Efficacy and safety of leucine + HMB consumption was invoked but never defined (see the help page).
  18. ^ Cite error: The named reference Discovered was invoked but never defined (see the help page).
  19. ^ Cite error: The named reference Lifestyle medicine WADA+NCAA was invoked but never defined (see the help page).
  20. ^ Cite error: The named reference WADA banned substances list was invoked but never defined (see the help page).
  21. ^ Cite error: The named reference NCAA banned substances list was invoked but never defined (see the help page).
  22. ^ Cite error: The named reference PEDs in sports 2015 review was invoked but never defined (see the help page).
  23. ^ Cite error: The named reference NCAA 2006 study was invoked but never defined (see the help page).
  24. ^ Cite error: The named reference HMB clinical evidence in sarcopenia 2017 review was invoked but never defined (see the help page).


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