3-Aminoisobutyric acid

3-Aminoisobutyric acid
Names
	Preferred IUPAC name 3-Amino-2-methylpropanoic acid
	Other names 3-Aminoisobutyrate
Identifiers
CAS Number	144-90-1 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:27389 ;
ChemSpider	58481 ;
ECHA InfoCard	100.005.132
KEGG	C05145 ;
PubChem CID	64956;
UNII	T68ALE2O9F ;
CompTox Dashboard (EPA)	DTXSID10861821 ;
	InChI InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7) Key: QCHPKSFMDHPSNR-UHFFFAOYSA-N ; InChI=1/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7) Key: QCHPKSFMDHPSNR-UHFFFAOYAN;
	SMILES CC(CN)C(=O)O; O=C(O)C(C)CN;
Properties
Chemical formula	C4H9NO2
Molar mass	103.12 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

3-Aminoisobutyric acid (also known as β-aminoisobutyric acid or BAIBA) is a product formed by the catabolism of thymine.

During exercise, the increase of PGC-1α protein triggers the secretion of BAIBA from exercising muscles to blood (concentration 2 to 3 μM in human serum). When BAIBA reaches the white fat tissue, it activates the expression of thermogenic genes via PPARα receptors, resulting in a browning of white fat cells.^[1] One of the consequences of the BAIBA activity is the increase of the background metabolism of the BAIBA target cells.

It is thought to play a number of roles in cell metabolism, how body burns fat and regulates insulin, triglycerides, and total cholesterol.^[2]^[3]^[4]

BAIBA is found as a normal metabolite of skeletal muscle in 2014. The plasma concentrations are increased in human by exercise. The production is likely a result of enhanced mitochondrial activity as the increase is also observed in the muscle of PGC-1a overexpression mice. BAIBA is proposed as protective factor against metabolic disorder since it can induce brown fat function.^[1]

References

^ ^a ^b Roberts LD, Boström P, O'Sullivan JF, Schinzel RT, Lewis GD, Dejam A, et al. (7 January 2014). "β-Aminoisobutyric acid induces browning of white fat and hepatic β-oxidation and is inversely correlated with cardiometabolic risk factors". Cell Metabolism. 19 (1): 96–108. doi:10.1016/j.cmet.2013.12.003. PMC 4017355. PMID 24411942.
^ Begriche K, Massart J, Fromenty B (June 2010). "Effects of β-aminoisobutyric acid on leptin production and lipid homeostasis: mechanisms and possible relevance for the prevention of obesity". Fundamental & Clinical Pharmacology. 24 (3): 269–82. doi:10.1111/j.1472-8206.2009.00765.x. PMID 19735301. S2CID 2520238.
^ Ibrahim A, Neinast M, Arany ZP (June 2017). "Myobolites: muscle-derived metabolites with paracrine and systemic effects". Current Opinion in Pharmacology. 34: 15–20. doi:10.1016/j.coph.2017.03.007. PMC 5651206. PMID 28441626.
^ Tanianskii DA, Jarzebska N, Birkenfeld AL, O'Sullivan JF, Rodionov RN (February 2019). "Beta-Aminoisobutyric Acid as a Novel Regulator of Carbohydrate and Lipid Metabolism". Nutrients. 11 (3): 524. doi:10.3390/nu11030524. PMC 6470580. PMID 30823446.

[Roberts-1] Roberts LD, Boström P, O'Sullivan JF, Schinzel RT, Lewis GD, Dejam A, et al. (7 January 2014). "β-Aminoisobutyric acid induces browning of white fat and hepatic β-oxidation and is inversely correlated with cardiometabolic risk factors". Cell Metabolism. 19 (1): 96–108. doi:10.1016/j.cmet.2013.12.003. PMC 4017355. PMID 24411942.

[2] Begriche K, Massart J, Fromenty B (June 2010). "Effects of β-aminoisobutyric acid on leptin production and lipid homeostasis: mechanisms and possible relevance for the prevention of obesity". Fundamental & Clinical Pharmacology. 24 (3): 269–82. doi:10.1111/j.1472-8206.2009.00765.x. PMID 19735301. S2CID 2520238.

[3] Ibrahim A, Neinast M, Arany ZP (June 2017). "Myobolites: muscle-derived metabolites with paracrine and systemic effects". Current Opinion in Pharmacology. 34: 15–20. doi:10.1016/j.coph.2017.03.007. PMC 5651206. PMID 28441626.

[4] Tanianskii DA, Jarzebska N, Birkenfeld AL, O'Sullivan JF, Rodionov RN (February 2019). "Beta-Aminoisobutyric Acid as a Novel Regulator of Carbohydrate and Lipid Metabolism". Nutrients. 11 (3): 524. doi:10.3390/nu11030524. PMC 6470580. PMID 30823446.

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[3]

[4]

See also

References