Page last updated: 2024-09-21

alpha-hydroxy-gamma-methylmercaptobutyric acid

Description

alpha-hydroxy-gamma-methylmercaptobutyric acid: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11427
CHEMBL ID2104213
CHEBI ID137228
SCHEMBL ID167046
MeSH IDM0052206

Synonyms (57)

Synonym
z94465h1y7 ,
2-hydroxy-4-(methylthio) butanoic acid
unii-z94465h1y7
butyric acid, 2-hydroxy-4-(methylthio)-
butanoic acid, 2-hydroxy-4-(methylthio)-
alpha-hydroxy-gamma-(methylthio)butyric acid
alimet
2-hydroxy-4-(methylthio)butanoic acid
mha-fa
hsdb 5700
dl-2-hydroxy-4-methylthiobuttersaeure
(+-)-2-hydroxy-4-(methylthio)butyric acid
alpha-hydroxy-gamma-methylmercaptobutyric acid
2-hydroxy-4-(methylthio)butyric acid
gamma-(methylthio)-alpha-hydroxybutyric acid
alpha-hydroxy-gamma-(methylmercapto)butyric acid
mha acid
(rs)-3-hydroxy-4-(methylthio)buttersaeure
desmeninol [inn]
einecs 209-523-0
CHEBI:137228
desmeninol
2-hydroxy-4-methylsulfanylbutanoic acid
583-91-5
H0654
2-hydroxy-4-methylthiobutanoic acid
CHEMBL2104213
FT-0612550
AKOS009157403
dl-2-hydroxy-4-methylthio-butanoic acid
2-hydroxy-4-methylthio-butanoic acid, (+/-)-
(+/-)-2-hydroxy-4-(methylthio)butyric acid
desmeninol [who-dd]
desmeninol [hsdb]
ONFOSYPQQXJWGS-UHFFFAOYSA-N
2-hydroxy-4-(methylthio)-butanoic acid
2-hydroxy-4-(methylsulfanyl)butanoic acid
SCHEMBL167046
W-105391
2-hydroxy-4-(methylthio)butyricacid
LMFA01050480
dl-2-hydroxy-4-(methylthio)butyric acid
mfcd00070490
SR-01000944858-1
sr-01000944858
H11809
(+/-)-2-hydroxy-4-(methylthio)butanoic acid
2-hydroxy-4-(methylthio)-butyric acid
4857-44-7 (calcium[2:1] salt)
FT-0699945
DTXSID50862236
EN300-103144
Q27295171
A869459
4-methylsulfanyl-2-oxidanyl-butanoic acid
Z788000926
2-hydroxy-4-(methylthio)butyric acid, tech grade

Drug Classes (1)

ClassDescription
thia fatty acidAny fatty acid having at least one of the chain methylene groups replaced by sulfur. Members of this group are believed to have important pharmacological (antioxidant and antiatherosclerosis) properties.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1130306Inhibition of glycolic acid oxidase (unknown origin) assessed as enzyme-mediated reduction of NaDCIP by sodium glycolate after 1 to 3 mins by spectrophotometer analysis1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Quantitative structure-activity relationships involving the inhibition of glycolic acid oxidase by derivatives of glycolic and glyoxylic acids.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (167)

TimeframeStudies, This Drug (%)All Drugs %
pre-199040 (23.95)18.7374
1990's23 (13.77)18.2507
2000's49 (29.34)29.6817
2010's47 (28.14)24.3611
2020's8 (4.79)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials14 (8.24%)5.53%
Reviews3 (1.76%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other153 (90.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (1)

ArticleYear
Elimination of adverse effects of ethoxyquin (EQ) by methionine hydroxy analog (MHA). Protective effects of EQ and MHA for bitterweed poisoning in sheep.
Toxicology letters, Volume: 16, Issue: 1-2
1983
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (12)

ArticleYear
Bioavailability of the dl-methionine and the calcium salt of dl-methionine hydroxy analog compared with l-methionine for nitrogen retention in starter pigs.
Journal of animal science, Jun-01, Volume: 99, Issue: 6
2021
Bioavailability of the calcium salt of dl-methionine hydroxy analog compared with dl-methionine for nitrogen retention and the preference of nursery pigs for diets based on the 2 forms of methionine.
Journal of animal science, Dec-01, Volume: 98, Issue: 12
2020
Bioavailability of different dietary supplemental methionine sources in animals.
Frontiers in bioscience (Elite edition), 06-01, Volume: 7, Issue: 3
2015
Bioavailability of methionine hydroxy analog-calcium salt relative to DL-methionine to support nitrogen retention and growth in starter pigs.
Animal : an international journal of animal bioscience, Volume: 6, Issue: 11
2012
Methionine availability in plasma of dairy cows supplemented with methionine hydroxy analog isopropyl ester.
Journal of dairy science, Volume: 88, Issue: 10
2005
Metal chelates of 2-hydroxy-4-methylthiobutanoic acid in animal feeding. Part 2: Further characterizations, in vitro and in vivo investigations.
Journal of inorganic biochemistry, Volume: 99, Issue: 2
2005
Estimation of bioavailability of DL-methionine hydroxy analogue relative to DL-methionine in layers with exponential and slope-ratio models.
Poultry science, Volume: 83, Issue: 9
2004
Metal chelates of 2-hydroxy-4-methylthiobutanoic acid in animal feeding: preliminary investigations on stability and bioavailability.
Journal of inorganic biochemistry, Jun-01, Volume: 95, Issue: 2-3
2003
Comparative absorption of 2-hydroxy-4-(methylthio)-butanoic acid and L-methionine in the broiler chick.
The Journal of nutrition, Volume: 114, Issue: 11
1984
Absorption of 14C-2-hydroxy-4-(methylthio)butanoic acid (Alimet) from the hindgut of the broiler chick.
Poultry science, Volume: 67, Issue: 9
1988
Absorption and bioavailability of DL-methionine hydroxy analog compared to DL-methionine.
Poultry science, Volume: 69, Issue: 2
1990
Bioavailability of methionine-hydroxy-analog free acid and S-methyl-methionine in the growing rat.
Acta veterinaria Hungarica, Volume: 40, Issue: 3
1992
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (13)

ArticleYear
Kinetics of microbial methionine metabolism in continuous cultures administered different methionine sources.
Journal of dairy science, Volume: 98, Issue: 2
2015
Assessing the ruminal action of the isopropyl ester of 2-hydroxy-4-(methylthio) butanoic acid in continuous and batch cultures of mixed ruminal microbes.
Journal of dairy science, Volume: 98, Issue: 2
2015
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 of the science of food and agriculture, Volume: 91, Issue: 12
2011
Assessment of ruminal bacterial populations and protozoal generation time in cows fed different methionine sources.
Journal of dairy science, Volume: 90, Issue: 2
2007
Evidence for 2-hydroxy-4(methylthio) butanoic acid and DL-methionine having different dose responses in growing broilers.
Poultry science, Volume: 85, Issue: 8
2006
Effects of zinc and sodium monensin on ruminal degradation of lysine-HCl and liquid 2-hydroxy-4-methylthiobutanoic acid.
Journal of dairy science, Volume: 87, Issue: 8
2004
Rumen degradation and availability of various amounts of liquid methionine hydroxy analog in lactating dairy cows.
Journal of dairy science, Volume: 85, Issue: 4
2002
Ruminal escape, gastrointestinal absorption, and response of serum methionine to supplementation of liquid methionine hydroxy analog in dairy cows.
Journal of dairy science, Volume: 82, Issue: 2
1999
The relative effectiveness of 2-hydroxy-4-(methylthio) butanoic acid and DL-methionine in young swine.
Journal of animal science, Volume: 76, Issue: 3
1998
Liquid methionine hydroxy analog (free acid) and DL-methionine attenuate calcium-induced kidney damage in domestic fowl.
Poultry science, Volume: 72, Issue: 7
1993
Studies of the renal excretion of the hydroxyl analogue of methionine by the chick.
Poultry science, Volume: 65, Issue: 7
1986
Nutritional value and safety of methionine derivatives, isomeric dipeptides and hydroxy analogs in mice.
The Journal of nutrition, Volume: 118, Issue: 3
1988
Absorption of 14C-2-hydroxy-4-(methylthio)butanoic acid (Alimet) from the hindgut of the broiler chick.
Poultry science, Volume: 67, Issue: 9
1988
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]