β-Hydroxy β-methylbutyric acid

β-Hydroxy β-methylbutyric acid
	Top: β-Hydroxy β-methylbutyric acid; Bottom: β-Hydroxy β-methylbutyrate
Clinical data
Other names	Conjugate acid form:; β-hydroxyisovaleric acid; 3-hydroxyisovaleric acid; Conjugate base form:; hydroxymethylbutyrate
Routes of; administration	By mouth or nasogastric
ATC code	none;
Legal status
Legal status	US: Dietary supplement; UN: Unscheduled;
Pharmacokinetic data
Metabolites	HMB-CoA, HMG-CoA, mevalonate, cholesterol, acetyl-CoA, acetoacetate, β-hydroxybutyrate
Onset of action	HMB-FA: 30–60 minutes; HMB-Ca: 1–2 hours
Elimination half-life	HMB-FA: 3 hours; HMB-Ca: 2.5 hours
Excretion	Renal (10–40% excreted)
Identifiers
	IUPAC name 3-hydroxy-3-methylbutanoic acid;
CAS Number	625-08-1 ;
PubChem CID	69362;
ChemSpider	62571 ;
UNII	3F752311CD;
KEGG	C20827 ;
ChEBI	CHEBI:37084 ;
CompTox Dashboard (EPA)	DTXSID20211535 ;
ECHA InfoCard	100.128.078
Chemical and physical data
Formula	C5H10O3
Molar mass	118.132 g·mol−1
3D model (JSmol)	Interactive image;
Density	~1.1 g/cm3 at 20 °C
Melting point	−80 °C (−112 °F) (glass)
Boiling point	128 °C (262 °F) at 7 mmHg
	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) ; Key:AXFYFNCPONWUHW-UHFFFAOYSA-N ;
	(verify)

β-Hydroxy β-methylbutyric acid (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. 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. 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. HMB produces these effects in part by stimulating the production of proteins and inhibiting the breakdown of proteins in muscle tissue. No adverse effects from long-term use as a dietary supplement in adults have been found.

HMB is sold as a dietary supplement at a cost of about US$30–50 per month when taking 3 grams per day. HMB is also contained in several nutritional products, including certain formulations of Ensure and Juven. HMB is also present in insignificant quantities in certain foods, such as alfalfa, asparagus, avocados, cauliflower, grapefruit, and catfish.

The effects of HMB on human skeletal muscle were first discovered by Steven L. Nissen at Iowa State University in the mid-1990s. 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. In 2006, only about 2% of college student athletes in the United States used HMB as a dietary supplement. As of 2017, HMB has found widespread use as an ergogenic supplement among young athletes.

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