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583-91-5,MFCD00070490
Catalog No.:AA003HBD
583-91-5 | 2-Hydroxy-4-(methylthio)butyric acid
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Technical Information
Catalog Number:
AA003HBD
Chemical Name:
2-Hydroxy-4-(methylthio)butyric acid
CAS Number:
583-91-5
Molecular Formula:
C5H10O3S
Molecular Weight:
150.1961
MDL Number:
MFCD00070490
IUPAC Name:
2-hydroxy-4-methylsulfanylbutanoic acid
InChI:
InChI=1S/C5H10O3S/c1-9-3-2-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)
InChI Key:
ONFOSYPQQXJWGS-UHFFFAOYSA-N
SMILES:
CSCCC(C(=O)O)O
EC Number:
209-523-0
Properties
Computed Properties
 
Complexity:
94.2  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
150.035g/mol
Formal Charge:
0
Heavy Atom Count:
9  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
150.192g/mol
Monoisotopic Mass:
150.035g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
82.8A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
0.2  

Synonyms
 
(+-)-isomer of alpha-hydroxy-gamma-methylmercaptobutyric acid 
2-hydroxy-4-methylthiobutanoic acid 
alpha-hydroxy-gamma-methylmercaptobutyric acid, monosodium salt (S)-isomer 
alpha-hydroxy-gamma-methylthiobutyrate 
alpha-hydroxymethionine 
methionine hydroxy analog 
2-Hydroxy-4-(methylthio)butyric acid 
583-91-5 
Alimet 
Desmeninol 
2-Hydroxy-4-(methylthio)butanoic acid 
MHA acid 
2-hydroxy-4-methylthiobutyrate 
Desmeninol [INN] 
MHA-FA 
Methionine hydroxy analog 
Butanoic acid, 2-hydroxy-4-(methylthio)- 
2-hydroxy-4-(methylsulfanyl)butanoic acid 
2-Hydroxy-4-(methylthio) butanoic acid 
HSDB 5700 
alpha-Hydroxy-gamma-(methylthio)butyric acid 
gamma-(Methylthio)-alpha-hydroxybutyric acid 
EINECS 209-523-0 
4-methylthio-2-hydroxybutyrate 
alpha-Hydroxy-gamma-(methylmercapto)butyric acid 
DL-2-Hydroxy-4-methylthiobuttersaeure 
2-hydroxy-4-(methylthio)-butanoic acid 
Butyric acid, 2-hydroxy-4-(methylthio)- 
(RS)-3-Hydroxy-4-(methylthio)buttersaeure 
(+-)-2-Hydroxy-4-(methylthio)butyric acid 
alpha-Hydroxy-gamma-methylmercaptobutyric acid 
2-hydroxy-4-methylsulfanylbutanoic acid 
2-Hydroxy-4-methylthiobutanoic acid 
ACMC-20anth 
Alimet 
2-HYDROXY-4-(METHYLTHIO)BUTYRICACID 
AC1L1XC1 
SCHEMBL167046 
CHEMBL2104213 
CTK1H0720 
CHEBI:137228 
ONFOSYPQQXJWGS-UHFFFAOYSA-N 
KS-000013YO 
LMFA01050480 
MFCD00070490 
alpha-hydroxy-gamma-methylmercaptobutyric acid 
AKOS009157403 
2-hydroxy-4-(methylthio)-butyric acid 
RP21393 
2-hydroxy-4-methylsulfanyl-butanoic acid 
4857-44-7 (calcium[2:1] salt) 
AN-21496 
DL-2-Hydroxy-4-(methylthio)butyric acid 
LS-48067 
DB-006142 
TC-030545 
alpha-hydroxy-gamma-methylmercaptobutyric acid, calcium salt 
FT-0080739 
FT-0612550 
(+/-)-2-Hydroxy-4-(methylthio)butanoic acid 
SR-01000944858 
I04-1355 
SR-01000944858-1 
W-105391 
2-Hydroxy-4-(methylthio)butyricAcid(65-72%inWater) 
HBA (CHRIS Code) 
UNII-Z94465H1Y7 
alpha-hydroxy-gamma-methylmercaptobutyric acid, calcium salt (2:1) 
Hydroxy analogue of methionine 
C5H10O3S 
C5-H10-O3-S 
CID11427 
RW1449 
ACN-038034 
Z94465H1Y7 
H0654 
MHA 
2-Hydroxy-4-(mehtylthio)Butirc Acid/Alpha-hydroxy-methionine 
alpha-hydroxy-gamma-methylmercaptobutyric acid, calcium salt(+-)-isomer 
alpha-hydroxy-gamma-methylmercaptobutyric acid, monosodium salt 
Literature

Title: Effects of dietary methionine source on productive performance, blood chemical, and hematological profiles in broiler chickens under tropical conditions.

Journal: Tropical animal health and production 20121201

Title: Bioavailability of methionine hydroxy analog-calcium salt relative to DL-methionine to support nitrogen retention and growth in starter pigs.

Journal: Animal : an international journal of animal bioscience 20121101

Title: Effect of supplementary concentrate type on nitrogen partitioning in early lactation dairy cows offered perennial ryegrass-based pasture.

Journal: Journal of dairy science 20120801

Title: Effects of graded levels of dietary methionine hydroxy analogue on immune response and antioxidant status of immune organs in juvenile Jian carp (Cyprinus carpio var. Jian).

Journal: Fish & shellfish immunology 20120501

Title: Application of ultra-performance liquid chromatography coupled with mass spectrometry to metabonomic study on spontaneously hypertensive rats and intervention effects of Ping Gan prescription.

Journal: Journal of separation science 20120201

Title: Effects of dietary protein content and 2-hydroxy-4-methylthiobutanoic acid or DL-methionine supplementation on performance and oxidative status of broiler chickens.

Journal: The British journal of nutrition 20111201

Title: Effects of dietary supplementation of methionine and its hydroxy analog DL-2-hydroxy-4-methylthiobutanoic acid on growth performance, plasma hormone levels, and the redox status of broiler chickens exposed to high temperatures.

Journal: Poultry science 20111001

Title: Effect of forage source and a supplementary methionine hydroxy analog on nitrogen balance in lactating dairy cows offered a low crude protein diet.

Journal: Journal of dairy science 20111001

Title: Comparative in vivo antioxidant capacity of DL-2-hydroxy-4-methylthiobutanoic acid (HMTBA) and DL-methionine in male mice fed a high-fat diet.

Journal: Journal of the science of food and agriculture 20110901

Title: Intestinal cell conversion of DL-2-hydroxy-(4-methylthio)butanoic acid in vitro: dietary up-regulation by this methionine precursor.

Journal: The British journal of nutrition 20110801

Title: The site of intestinal disappearance of DL-methionine and methionine hydroxy analog differs in pigs.

Journal: Journal of animal science 20110501

Title: Effect of feeding different sources of rumen-protected methionine on milk production and N-utilization in lactating dairy cows.

Journal: Journal of dairy science 20110401

Title: Metabolism of 2-hydroxy-4-(methylthio)butanoate (HMTBA) in lactating dairy cows.

Journal: Journal of dairy science 20110301

Title: Effects of dietary supplementation of methionine and lysine on milk production and nitrogen utilization in dairy cows.

Journal: Journal of dairy science 20100801

Title: Effects of adding liquid DL-methionine hydroxy analogue-free acid to drinking water on growth performance and small intestinal morphology of nursery pigs.

Journal: Journal of animal physiology and animal nutrition 20100601

Title: Effects of dl-2-hydroxy-4-methylthiobutyrate on the first-pass intestinal metabolism of dietary methionine and its extra-intestinal availability.

Journal: The British journal of nutrition 20100301

Title: Short communication: transport of 2-hydroxy-4-methyl-thio-butanoic isopropyl ester by rumen epithelium in vitro.

Journal: Journal of dairy science 20100101

Title: Effects of providing two forms of supplemental methionine to periparturient Holstein dairy cows on feed intake and lactational performance.

Journal: Journal of dairy science 20091001

Title: Apparent absorption of methionine and 2-hydroxy-4-methylthiobutanoic acid from gastrointestinal tract of conventional and gnotobiotic pigs.

Journal: Animal : an international journal of animal bioscience 20091001

Title: Molecular analysis of microbial community structure in the chicken ileum following organic acid supplementation.

Journal: Veterinary microbiology 20090612

Title: Effects of 2-hydroxy-4-methylthiobutyrate on portal plasma flow and net portal appearance of amino acids in piglets.

Journal: Amino acids 20090301

Title: Effects of 2-hydroxy-4-(methylthio)-butanoic acid on performance and carcass characteristics of finishing beef cattle and on fermentation in continuous culture.

Journal: Journal of animal science 20080801

Title: Effects of liquid DL-2-hydroxy-4-methylthio butanoic acid on growth performance and immune responses in broiler chickens.

Journal: Poultry science 20080701

Title: Partial Na+ dependence of DL-2-hydroxy-4-(methylthio)butanoic acid uptake in the chicken small intestine.

Journal: Poultry science 20080701

Title: The effect of several organic acids on phytate phosphorus hydrolysis in broiler chicks.

Journal: Poultry science 20080401

Title: Effect of different dietary methionine sources on intestinal microbial populations in broiler chickens.

Journal: Poultry science 20071101

Title: Effects of rumen-undegradable protein sources and supplemental 2-hydroxy-4-(methylthio)-butanoic acid and lysine-HCl on lactation performance in dairy cows.

Journal: Journal of dairy science 20071101

Title: Effect of excess methionine and methionine hydroxy analogue on growth performance and plasma homocysteine of growing Pekin ducks.

Journal: Poultry science 20070901

Title: Short communication: Absorption of 2-hydroxy-4-methylthiobutanoate in dairy cows.

Journal: Journal of dairy science 20070601

Title: Determining the methionine activity of Mintrex organic trace minerals in broiler chicks by using radiolabel tracing or growth assay.

Journal: Poultry science 20070501

Title: Impact of feeding 2-hydroxy-4-(methylthio)butanoic acid and DL-methionine supplemented maize-soybean-rapeseed meal diets on growth performance and carcase quality of broilers.

Journal: British poultry science 20070401

Title: Evidence of a different dose response in turkeys when fed 2-hydroxy-4(methylthio) butanoic acid versus DL-methionine.

Journal: Poultry science 20070301

Title: Assessment of ruminal bacterial populations and protozoal generation time in cows fed different methionine sources.

Journal: Journal of dairy science 20070201

Title: Multidimensional chromatographic approach applied to the identification of novel aroma compounds in wine. Identification of ethyl cyclohexanoate, ethyl 2-hydroxy-3-methylbutyrate and ethyl 2-hydroxy-4-methylpentanoate.

Journal: Journal of chromatography. A 20061229

Title: No evidence for different dose responses of commercial methionine sources in broilers.

Journal: Poultry science 20061201

Title: Conversion of the methionine hydroxy analogue DL-2-hydroxy-(4-methylthio) butanoic acid to sulfur-containing amino acids in the chicken small intestine.

Journal: Poultry science 20061101

Title: Effect of different forms of methionine on lactational performance of dairy cows.

Journal: Journal of dairy science 20061101

Title: Homocysteine remethylation in broilers fed surfeit choline or betaine and varying levels and sources of methionine from eight to twenty-two days of age.

Journal: Poultry science 20061001

Title: Absorption and digestive tract metabolism of 2-hydroxy-4-methylthiobutanoic acid in lambs.

Journal: Journal of dairy science 20060901

Title: Concentrations of putrescine, spermidine, and spermine in duodenum and pancreas as affected by the ratio of arginine to lysine and source of methionine in broilers under heat stress.

Journal: Poultry science 20060801

Title: Evidence for 2-hydroxy-4(methylthio) butanoic acid and DL-methionine having different dose responses in growing broilers.

Journal: Poultry science 20060801

Title: Effects of dietary supplementation of DL-methionine or 2-hydroxy-4-(methylthio)-butanoic acid on food intake, nutrient digestibility, nitrogen balance, and urinary and blood metabolites in healthy, growing dogs.

Journal: Archives of animal nutrition 20060801

Title: Estimation of the true ileal digestible lysine and sulfur amino acid requirement and comparison of the bioefficacy of 2-hydroxy-4-(methylthio)butanoic acid and DL-methionine in eleven- to twenty-six-kilogram nursery pigs.

Journal: Journal of animal science 20060701

Title: Appropriate statistical methods to compare dose responses of methionine sources.

Journal: Poultry science 20060501

Title: A multiple regression model approach to contrast the performance of 2-hydroxy-4-methylthio butanoic acid and DL-methionine supplementation tested in broiler experiments and reported in the literature.

Journal: Poultry science 20060401

Title: Hepatic metabolism of 2-hydroxy-4-methylthiobutyrate in growing lambs.

Journal: Journal of dairy science 20060301

Title: Absorption of 2-hydroxy-4-methylthiobutyrate and conversion to methionine in lambs.

Journal: Journal of dairy science 20060301

Title: Oligomers are not the limiting factor in the absorption of DL-2-hydroxy-4-(methylthio)butanoic acid in the chicken small intestine.

Journal: Poultry science 20060101

Title: Estimation of the ideal ratio of true ileal digestible sulfur amino acids:lysine in 8- to 26-kg nursery pigs.

Journal: Journal of animal science 20051101

Title: Methionine availability in plasma of dairy cows supplemented with methionine hydroxy analog isopropyl ester.

Journal: Journal of dairy science 20051001

Title: The effects of various organic acids on phytate phosphorus utilization in chicks.

Journal: Poultry science 20050901

Title: Comparative in vitro and in vivo absorption of 2-hydroxy-4(methylthio) butanoic acid and methionine in the broiler chicken.

Journal: Poultry science 20050901

Title: Effects of 2-hydroxy-4-(methylthio) butanoic acid (HMB) and its isopropyl ester on milk production and composition by Holstein cows.

Journal: Journal of dairy science 20050701

Title: Metal chelates of 2-hydroxy-4-methylthiobutanoic acid in animal feeding. Part 2: Further characterizations, in vitro and in vivo investigations.

Journal: Journal of inorganic biochemistry 20050201

Title: The influence of dietary sodium chloride, arginine:lysine ratio, and methionine source on apparent ileal digestibility of arginine and lysine in acutely heat-stressed broilers.

Journal: Poultry science 20050201

Title: Determination of rumen degradability and ruminal effects of three sources of methionine in lactating cows.

Journal: Journal of dairy science 20050101

Title: Estimation of bioavailability of DL-methionine hydroxy analogue relative to DL-methionine in layers with exponential and slope-ratio models.

Journal: Poultry science 20040901

Title: Effects of zinc and sodium monensin on ruminal degradation of lysine-HCl and liquid 2-hydroxy-4-methylthiobutanoic acid.

Journal: Journal of dairy science 20040801

Title: Feeding 2-hydroxy-4-(methylthio)-butanoic acid to periparturient dairy cows improves milk production but not hepatic metabolism.

Journal: Journal of dairy science 20040401

Title: Catabolism of volatile sulfur compounds precursors by Brevibacterium linens and Geotrichum candidum, two microorganisms of the cheese ecosystem.

Journal: Journal of biotechnology 20031106

Title: Adaptations in body muscle and fat in transition dairy cattle fed differing amounts of protein and methionine hydroxy analog.

Journal: Journal of dairy science 20031101

Title: Effects of 2-hydroxy-4-(methylthio) butanoic acid (HMB) on microbial growth in continuous culture.

Journal: Journal of dairy science 20030801

Title: Absorption of methionine and 2-hydroxy-4-methylthiobutoanic acid in conventional and germ-free chickens.

Journal: Poultry science 20030701

Title: Metal chelates of 2-hydroxy-4-methylthiobutanoic acid in animal feeding: preliminary investigations on stability and bioavailability.

Journal: Journal of inorganic biochemistry 20030601

Title: Enzymatic synthesis and characterization of l-methionine and 2-hydroxy-4-(methylthio)butanoic acid (HMB) co-oligomers.

Journal: Journal of agricultural and food chemistry 20030423

Title: Effects of calcium salts of fatty acids and calcium salt of methionine hydroxy analogue on plasma prostaglandin F2alpha metabolite and milk fatty acid profiles in late lactation Holstein-Friesian cows.

Journal: Theriogenology 20021101

Title: Relative effectiveness of methionine hydroxy analog compared to DL-methionine in broiler chickens.

Journal: Poultry science 20020601

Title: Rumen degradation and availability of various amounts of liquid methionine hydroxy analog in lactating dairy cows.

Journal: Journal of dairy science 20020401

Title: [The feed value in growing pigs of a new cultivar of field beans (Vicia faba L.) supplemented with DL-methionine or DL-methionine-hydroxyanalog].

Journal: Journal of animal physiology and animal nutrition 20020201

Title: Uptake of DL-2-hydroxy-4-methylthio-butanoic acid (DL-HMB) in the broiler liver in vivo.

Journal: Poultry science 20011101

Title: The hepatic extraction of plasma free amino acids and response to hepatic portal venous infusion of methionine sources in anesthetized SCWL males (Gallus domesticus).

Journal: Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20010901

Title: Lactobacillus casei and Lactobacillus plantarum initiate catabolism of methionine by transamination.

Journal: Journal of applied microbiology 20010601

Title: Effects of alimet on nutrient digestibility, bacterial protein synthesis, and ruminal disappearance during continuous culture.

Journal: Journal of dairy science 20010101

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