2-Hydroxy-4-(methylthio)butanoic acid supplier

Name
2-HYDROXY-4-(METHYLTHIO)BUTYRIC ACID
EINECS 209-523-0
CAS No. 583-91-5
Article Data27
CAS DataBase
Density 1.277 g/cm³
Solubility
Melting Point
Formula C₅H₁₀O₃S
Boiling Point 316.5 °C at 760 mmHg
Molecular Weight 150.199
Flash Point 145.2 °C
Transport Information
Appearance Light brown liquid
Safety 26-36/37/39-45
Risk Codes 23/24/25
Molecular Structure
Hazard Symbols
Synonyms Butyricacid, 2-hydroxy-4-(methylthio)- (6CI,8CI);Butyric acid, a-hydroxy-g-(methylmercapto)- (4CI);(+)-2-Hydroxy-4-(methylthio)butyric acid;2-Hydroxy-4-(methylmercapto)butyricacid;Butanoic acid,2-hydroxy-4-(methylthio)-;2-Hydroxy-4-(methylthio)butyricacid;Alimet;BIOX-A;DL-2-Hydroxy-4-(methylmercapto)butanoic acid;DL-2-Hydroxy-4-(methylmercapto)butyric acid;DL-2-Hydroxy-4-(methylthio)butanoic acid;DL-2-Hydroxy-4-(methylthio)butyricacid;DL-a-Hydroxy-g-methylmercaptobutyric acid;Desmenidol;Desmeninol;HMTBA;Hydan L;MHA acid;MHA-FA;a-Hydroxy-4-(methylthio)butyricacid;a-Hydroxy-g-(methylmercapto)butyric acid;a-Hydroxy-g-(methylthio)butyric acid;g-(Methylmercapto)-a-hydroxybutyric acid;g-(Methylthio)-a-hydroxybutyric acid;
PSA 82.83000
LogP 0.18500

Synthetic route

: 19444-84-9
3-hydroxyoxolan-2-one

: 5188-07-8
sodium thiomethoxide

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
Stage #1: 3-hydroxyoxolan-2-one; sodium thiomethoxide In N,N-dimethyl-formamide at 153℃; for 3h; Stage #2: With hydrogenchloride; water Product distribution / selectivity;	100%

: 17773-41-0
2-hydroxy-4-(methylthio)butyronitrile

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
With potassium phosphate buffer; nitrilase from Alcaligenes faecalis ATCC8750 at 30℃; for 48h; pH=7.3;	99%
Multi-step reaction with 2 steps 1: 83 percent / borax / KCN / H2O / 1.5 h / 80 °C 2: 90 percent / NaOH / H2O / 3 h / Heating View Scheme
Stage #1: 2-hydroxy-4-(methylthio)butyronitrile With sulfuric acid at 65℃; Stage #2: With water

: 49540-21-8
α-hydroxy-4-methylthiobutyramide

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
With sodium hydroxide In water for 3h; Heating;	90%
With sulfuric acid; water at 110℃; for 250 - 500h; Product distribution / selectivity;
With sulfuric acid; water at 100 - 105℃; Temperature;

: phosphoric acid 1,1-dicyano-3-methylsulfanyl-propyl ester diethyl ester

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
With hydrogenchloride for 5h; Heating;	85%

: 74-93-1
methylthiol

: 600-17-9
vinyl glycolic acid

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
With triethyl borane at 20℃; UV-irradiation;	85%

: 2-hydroxy-4-(methylthio)butanoic acid calcium salt

: 7664-93-9
sulfuric acid

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
In water for 1.5h;	85%

: 17773-41-0
2-hydroxy-4-(methylthio)butyronitrile

A: 49540-21-8
α-hydroxy-4-methylthiobutyramide

B: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
With borax; potassium cyanide In water at 80℃; for 1.5h;	A 83% B 8%
With sulfuric acid; water at 35 - 112℃; for 1.5 - 3.16667h; Product distribution / selectivity;
With sulfuric acid; water at 40 - 125℃; under 1875.19 Torr; for 2.25h; Product distribution / selectivity;
With sulfuric acid; water at 50 - 110℃; under 12 Torr; Product distribution / selectivity; Continuous process;

: 74-90-8
hydrogen cyanide

: 3268-49-3
3-(methylsulfenyl)propanal

A: 583-91-5
2-hydroxy 4-methylthiobutyric acid

B: 59-51-8
DL-methionine

Conditions

Conditions	Yield
With cerium(IV) oxide; ammonia In water at 75℃; for 6h;	A 62.1% B 34.9%
With cerium(IV) oxide; ammonia In water at 75℃; for 6h;	A 44.3% B 52.6%

...Expand

: 1003880-00-9
4-(methylthio)-2-oxo-1-butanol

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
Stage #1: 4-(methylthio)-2-oxo-1-butanol With potassium hydroxide; oxygen; copper diacetate In water at 20℃; for 2h; Stage #2: With sulfuric acid; water	46%

: 59-51-8
DL-methionine

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
With silver(I) nitrite; water

: 63-68-3
L-methionine

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
With cis-nitrous acid; sodium bromide In water at 25℃; Rate constant;

: 2-acetoxy-4-methylthiobutanenitrile

A: 583-91-5
2-hydroxy 4-methylthiobutyric acid

B: 138128-01-5
2-acetyloxy-4-(methylthio)butanoic acid

Conditions

Conditions	Yield
With potassium phosphate buffer; nitrilase from Alcaligenes faecalis ATCC8750 at 30℃; for 48h; pH=7.3; Title compound not separated from byproducts;	A 6 % Spectr. B 82 % Spectr.

: 74-90-8
hydrogen cyanide

: 3268-49-3
3-(methylsulfenyl)propanal

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
In water at 20 - 68℃; for 0.0833333h; pH=4.7 - 5.5;
Stage #1: hydrogen cyanide; 3-(methylsulfenyl)propanal With pyridine; acetic acid at 35 - 45℃; for 1.25h; Stage #2: With sulfuric acid; water at 60 - 90℃; for 2.91667h;

: 138128-01-5
2-acetyloxy-4-(methylthio)butanoic acid

A brucine salt: brucine salt

B: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
With brucine In ethanol

: 1-acetyloxy-3-methylthiopropene

(PPh3)2 PdCl2: (PPh3)2 PdCl2

: L-menthoxyethyl acetyl-L-2-hydroxy-4-methylthiobutyrate

: 2-(2-isopropyl-5-methylcyclohexyloxy)ethanol

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
With hydrogenchloride; CO In tetrahydrofuran

...Expand

: 1-carboxy-3-methylthiopropyl sulfate

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
With water at 80℃; for 24h; Purification / work up;

: 49540-21-8
α-hydroxy-4-methylthiobutyramide

A: 1-carboxy-3-methylthiopropyl sulfate

B: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
With sulfuric acid; water at 109℃; for 4h; Heating / reflux;

: 63302-72-7
2-hydroxy-4-methylthiobutyric acid ammonium salt

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
In water; 4-methyl-2-pentanone at 80 - 117℃; Product distribution / selectivity; Inert atmosphere;

: 51828-97-8
sodium α-keto-(γ-methylthio)butyrate

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
With hydrogen; rhodium contaminated with carbon In water at 50℃; under 7500.75 Torr; for 6h; Product distribution / selectivity; autoclave;

: 773837-37-9
sodium cyanide

: 3268-49-3
3-(methylsulfenyl)propanal

: 119353-03-6
3-(methylselenyl)-propanal

A: 873660-49-2
DL-α-hydroxyselenomethionine

B: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
Stage #1: 3-(methylsulfenyl)propanal; 3-(methylselenyl)-propanal With sodium hydrogensulfite In water at 20℃; for 0.166667h; Stage #2: sodium cyanide In water at 20℃; for 2h; Reflux; Stage #3: With hydrogenchloride; water for 5h; Reflux;

...Expand

: 52703-96-5
methyl 2-hydroxy-4-(methylthio)butanoate

A: 74-93-1
methylthiol

B: 583-91-5
2-hydroxy 4-methylthiobutyric acid

Conditions

Conditions	Yield
With sodium hydrosulfide monohydrate In dimethyl sulfoxide at 50℃; for 24h; Temperature; Inert atmosphere; Schlenk technique;	A n/a B 93 %Spectr.

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 2-hydroxy-4-(methylthio)butanoic acid calcium salt

Conditions

Conditions	Yield
With calcium oxide In ethanol at 100℃; for 24h; Reagent/catalyst;	98.09%
Stage #1: 2-hydroxy 4-methylthiobutyric acid With sodium hydroxide In water at 20℃; pH=~ 9.0; Stage #2: With calcium chloride In water at 20℃; for 5.5h;	84%
With calcium oxide In water at 120℃; Reagent/catalyst; Temperature;
Multi-step reaction with 2 steps 1.1: sodium hydroxide / 0.5 h / 20 °C 2.1: sodium hydroxide; water / 45 - 50 °C 2.2: 0.5 h View Scheme
Multi-step reaction with 2 steps 1.1: potassium hydroxide / methanol / 1 h / 0 °C 1.2: 0 °C 2.1: sodium hydroxide; water / 45 - 50 °C 2.2: 0.5 h View Scheme

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 503-38-8
trichloromethyl chloroformate

: 1161721-72-7
5-(2-(methylthio)ethyl)-1,3-dioxolan-2,4-dione

Conditions

Conditions	Yield
In tetrahydrofuran	97%

: 67-56-1
methanol

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 52703-96-5
methyl 2-hydroxy-4-(methylthio)butanoate

Conditions

Conditions	Yield
With sodium hydroxide at 20℃; for 0.5h;	91.7%

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 80-48-8
methyl p-toluene sulfonate

: 52703-96-5
methyl 2-hydroxy-4-(methylthio)butanoate

Conditions

Conditions	Yield
Stage #1: 2-hydroxy 4-methylthiobutyric acid With potassium hydroxide In ethanol at 20℃; for 0.5h; Stage #2: methyl p-toluene sulfonate In ethanol at 20℃;	90.3%

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 616-38-6
carbonic acid dimethyl ester

: 52703-96-5
methyl 2-hydroxy-4-(methylthio)butanoate

Conditions

Conditions	Yield
Stage #1: 2-hydroxy 4-methylthiobutyric acid With potassium hydroxide In methanol at 0℃; for 1h; Stage #2: carbonic acid dimethyl ester In methanol at 0℃;	90.1%

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 77-76-9
2,2-dimethoxy-propane

: 1161721-65-8
2,2-dimethyl-5-(2-(methylthio)ethyl)-1,3-dioxolan-4-one

Conditions

Conditions	Yield
In tetrahydrofuran	89%

BF3.2H2O: BF3.2H2O

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

MgBr2.2Et2O: MgBr2.2Et2O

: 1161721-65-8
2,2-dimethyl-5-(2-(methylthio)ethyl)-1,3-dioxolan-4-one

Conditions

Conditions	Yield
zinc(II) chloride In diethyl ether; water; acetone	87%

...Expand

: dichlorotricarbonylruthenium(II) dimer

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: Ru(CO)3Cl2(H3CS(CH2)2CH(OH)CO2H)

Conditions

Conditions	Yield
In acetone at 20℃; for 24h; Inert atmosphere; Schlenk technique;	83%

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 112-64-1
tetradecanoyl chloride

A: C14-HE

B: C14-HE

Conditions

Conditions	Yield
at 65℃; Overall yield = 2.6 g;	A 80.5% B 19.5%

...Expand

: 5419-55-6
Triisopropyl borate

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 57296-04-5
D,L-2-hydroxy-4-(methylthio)-butanoic acid isopropyl ester

Conditions

Conditions	Yield
at 95℃; for 10h;	72%

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 111-64-8
n-octanoic acid chloride

A: C8-HE

B: C8-HE

C: C8-HE

Conditions

Conditions	Yield
at 65℃;	A 25.6% B 5.3% C 68.4%

...Expand

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 111-27-3
hexan-1-ol

: 161193-00-6
2-hydroxy-4-(methylthio)butanoic acid hexyl ester

Conditions

Conditions	Yield
With sodium hydrogen sulfate In toluene for 5.5h; Dean-Stark; Reflux;	64.1%
With sodium hydrogen sulfate In toluene Dean-Stark; Reflux;	61.1%

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 75-36-5
acetyl chloride

: 138128-01-5
2-acetyloxy-4-(methylthio)butanoic acid

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	63.1%
Stage #1: 2-hydroxy 4-methylthiobutyric acid With triethylamine In dichloromethane at 0℃; Stage #2: acetyl chloride In dichloromethane at 0 - 20℃;	63.1%
With triethylamine In dichloromethane at 0 - 20℃;
at 20℃; for 3h; Temperature; Large scale;

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 71-36-3
butan-1-ol

: 2-hydroxy-4-(methylthio)butanoic acid butyl ester

Conditions

Conditions	Yield
With sodium hydrogen sulfate In toluene for 5h; Dean-Stark; Reflux;	62.3%

: 112-92-5
1-octadecanol

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 1446404-60-9
octadecyl 2-hydroxy-4-(methylthio)butanoate

Conditions

Conditions	Yield
With sodium hydrogen sulfate In toluene Dean-Stark; Reflux;	61%

: 108-21-4
Isopropyl acetate

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 57296-04-5
D,L-2-hydroxy-4-(methylthio)-butanoic acid isopropyl ester

Conditions

Conditions	Yield
With sulfuric acid at 80 - 90℃; for 6h; Temperature; Reagent/catalyst; Large scale;	57.5%

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 78-93-3
butanone

: 1161721-66-9
2-ethyl-2-methyl-5-(2-(methylthio)ethyl)-1,3-dioxolan-4-one

Conditions

Conditions	Yield
	56%

: 111-87-5
octanol

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 1446404-55-2
2-hydroxy-4-(methylthio)butanoic acid octyl ester

Conditions

Conditions	Yield
With sodium hydrogen sulfate In toluene Dean-Stark; Reflux;	45%
With sodium hydrogen sulfate In toluene for 5.5h; Dean-Stark; Reflux;	45%

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 112-67-4
n-hexadecanoyl chloride

: 4-(methylthio)-2-(palmitoyloxy)butanoic acid

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃;	45%

: 112-30-1
1-Decanol

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 161193-01-7
2-hydroxy-4-(methylthio)butyric acid decyl ester

Conditions

Conditions	Yield
With sodium hydrogen sulfate In toluene for 6h; Reflux;	44%
With sodium hydrogen sulfate In toluene Dean-Stark; Reflux;	43.5%
With sodium hydrogen sulfate In toluene for 6h; Dean-Stark;	43.5%

: 112-53-8
1-dodecyl alcohol

: 583-91-5
2-hydroxy 4-methylthiobutyric acid

: 1446404-58-5
dodecyl 2-hydroxy-4-(methylthio)butanoate

Conditions

Conditions	Yield
With sodium hydrogen sulfate In toluene Dean-Stark; Reflux;	42%

2-Hydroxy-4-(methylthio)butanoic acid Consensus Reports

Reported in EPA TSCA Inventory.

2-Hydroxy-4-(methylthio)butanoic acid Specification

The 2-Hydroxy-4-(methylthio)butanoic acid, with the CAS registry number 583-91-5,is also known as Desmeninol. It belongs to the product categories of Pharmaceuticals;Isotope Labelled Compounds. This chemical's molecular formula is C5H10O3S and molecular weight is 150.2. Its EINECS number is 209-523-0.What's more,Its systematic name is 2-Hydroxy-4-(methylthio)butanoic acid.It is a light brown liquid which is methionine hydroxy analogue.

Physical properties about 2-Hydroxy-4-(methylthio)butanoic acid are:
(1)ACD/LogP: 0.039; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.25; (4)ACD/LogD (pH 7.4): -3.58; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.529; (13)Molar Refractivity: 36.268 cm3; (14)Molar Volume: 117.547 cm3; (15)Surface Tension: 53.3240013122559 dyne/cm; (16)Density: 1.278 g/cm3; (17)Flash Point: 145.198 °C; (18)Enthalpy of Vaporization: 64.667 kJ/mol; (19)Boiling Point: 316.473 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C(O)C(O)CCSC;
(2)Std. InChI:InChI=1S/C5H10O3S/c1-9-3-2-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8);
(3)Std. InChIKey:ONFOSYPQQXJWGS-UHFFFAOYSA-N.

Safety Information of 2-Hydroxy-4-(methylthio)butanoic acid:
The 2-Hydroxy-4-(methylthio)butanoic acid is toxic by inhalation, in contact with skin and if swallowed.In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).When you use it ,wear suitable protective clothing, gloves and eye/face protection.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .

The toxicity data of 2-Hydroxy-4-(methylthio)butanoic acid:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	oral	3478mg/kg (3478mg/kg)		Toxicology Letters. Vol. 31(Suppl), Pg. 54, 1986.

Product Name

2-HYDROXY-4-(METHYLTHIO)BUTYRIC ACID

Synthetic route

2-Hydroxy-4-(methylthio)butanoic acid Consensus Reports

2-Hydroxy-4-(methylthio)butanoic acid Specification

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