L-Valine supplier | CasNO.72-18-4

Name
L-Valine
EINECS 200-773-6
CAS No. 72-18-4
Article Data340
CAS DataBase
Density 1.064 g/cm³
Solubility 85 g/L (20 °C) in water
Melting Point 295-300 °C (subl.)(lit.)
Formula C₅H₁₁NO₂
Boiling Point 213.642 °C at 760 mmHg
Molecular Weight 117.148
Flash Point 83.008 °C
Transport Information
Appearance White crystalline powder
Safety 24/25-36-22
Risk Codes 40
Molecular Structure
Hazard Symbols Xn
Synonyms Valine,L- (8CI);(+)-2-Amino-3-methylbutyric acid;(2S)-2-Amino-3-methylbutanoic acid;(S)-2-Amino-3-methylbutanoic acid;(S)-Valine;(S)-a-Amino-b-methylbutyric acid;2-Amino-3-methylbutanoic acid;Butanoic acid,2-amino-3-methyl-, (S)-;L-(+)-a-Aminoisovaleric acid;L-a-Amino-b-methylbutyricacid;NSC 76038;Valine;H-Val-OH;
PSA 63.32000
LogP 0.75460

Synthetic route

: 26081-00-5
N-carbamoyl-valine

: 72-18-4
L-valine

Conditions

Conditions	Yield
With NH4Cl-NH4OH buffer pH 8.5; nickel dichloride at 60℃; for 24h; N-carbamyl-L-amino acid aminohydrolase;	100%
With Tris-HCl buffer; N-carbamoyl-L-amino acid hydrolase; iron(II) sulfate at 30℃; for 2h;
With sodium phosphate buffer; N-carmamyl-L-amino acid aminohydrolase of Pseudomonas sp. strain NS671; water; manganese(II) at 30℃; for 0.5h; Product distribution;	18.9 mmol

: 439912-46-6
Proc-Val-OH

: 72-18-4
L-valine

Conditions

Conditions	Yield
With resin bound tetrathiomolybdate In methanol at 28℃; for 1.5h; ultrasonic bath;	100%

: 2C16H16O4*C5H11NO2

A: 72-18-4
L-valine

B: 178306-52-0
(S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid

Conditions

Conditions	Yield
In ethyl acetate at 80℃; for 3h; Solvent;	A 97% B 100%

: 2507-77-9
α-ketoisovalerate

: 72-18-4
L-valine

Conditions

Conditions	Yield
With ammonium formate; tris hydrochloride; nicotinamide adenine dinucleotide; formate dehydrogenase; phenylalanine dehydrogenase In water at 30℃; for 24h;	97%

: 269742-33-8
(2S)-2-(N-tert-Butoxycarbonyl)amino-3-methylbut-3-enoic acid

: 72-18-4
L-valine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃; for 3h; Catalytic hydrogenation;	94%

: 13734-41-3
t-Boc-L-valine

: 72-18-4
L-valine

Conditions

Conditions	Yield
With tetradecyl(trihexyl)phosphonium bistriflamide; trifluoroacetic acid at 130℃; for 0.166667h; Ionic liquid;	93%
at 140℃; for 2h;	70%
at 130℃; for 1h;
Multi-step reaction with 4 steps 1.1: triethylamine; chloroformic acid ethyl ester / dichloromethane / 1 h / 20 °C / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: hydrogenchloride / water; methanol / 4 h / 0 - 20 °C / Inert atmosphere 3.1: N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux 4.1: hydrogenchloride; acetic acid / water; toluene / 44 h / 110 °C / Inert atmosphere View Scheme

: 516-06-3
D,L-valine

: 72-18-4
L-valine

Conditions

Conditions	Yield
With D-amino acid oxidase; E. coli branched-chain amino acid aminotransferase In water at 37℃; for 72h; Tris buffer, pH 8.5, 1mM EDTA, monosodium glutamate, bovine serum albumin, catalase, pyridoxal 5'-phosphate;	90%
mit Hilfe eines Enzym-Praeparats aus Schweine-Nieren;
bei der Vergaerung mit Hefe unter Zusatz von Zucker;

: C5H11NO2*H3N*ClH

: 72-18-4
L-valine

Conditions

Conditions	Yield
With ruthenium nanoparticles dispersed in a polyvinylpyrrolidone matrix; amberlyst A-21 In methanol; dichloromethane	89%

: 68858-20-8
Fmoc-Val-OH

A: 72-18-4
L-valine

B: 4425-82-5
9-methylene-fluorene

Conditions

Conditions	Yield
With dimethyl sulfoxide at 120℃; for 0.25h; Microwave irradiation;	A 88% B n/a

: Nmoc-Val-OH

: 72-18-4
L-valine

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol; aq. phosphate buffer at 20℃; for 1.33333h; Cooling with ice; Sealed tube;	88%

: 127556-10-9
(2R)-N-<(2S)-2-<amino>-3-methylbutan-1-oyl>bornane-10,2-sultam

: 72-18-4
L-valine

Conditions

Conditions	Yield
With hydrogenchloride; lithium hydroxide 1.) THF/water, r.t., 24 h, 2.) THF/water 2 : 1, r.t., 24 h;	87%

: 15136-27-3
trans-cyclo(D-Ala-Val)

A: 338-69-2
D-Alanine

B: 72-18-4
L-valine

Conditions

Conditions	Yield
With hydrogenchloride; water	A 86% B n/a
With hydrogenchloride	A 86% B n/a
With hydrogenchloride; water for 24h; Heating;

: 631921-65-8
((S)-1-Cyano-2-methyl-propyl)-carbamic acid methyl ester

: 72-18-4
L-valine

Conditions

Conditions	Yield
With hydrogenchloride In water for 7h; Heating;	85%

: 108437-93-0
(2S,5S)-N-<(S)-N-bis(methylthio)methylenevalyl>-2,5-bis(methoxymethoxymethyl)pyrrolidine

: 72-18-4
L-valine

Conditions

Conditions	Yield
With hydrogenchloride for 4h; Heating;	81%

: (3RS,6S)-3-[di(methoxycarbonyl)methyl]-6-isopropyl-2,5-piperazinedione

A: 72-18-4
L-valine

B: 71855-54-4
D-aspartic acid hydrochloride

C: 17585-59-0
L-aspartic acid hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; water at 100℃; for 24h;	A 81% B n/a C n/a

...Expand

: 202347-80-6
(3S,5S)-3-Isopropyl-5-phenyl-morpholin-2-one

: 72-18-4
L-valine

Conditions

Conditions	Yield
With hydrogen; trifluoroacetic acid; palladium dihydroxide In methanol; water under 3750.3 Torr; for 24h;	78%

: 16652-76-9
L-valine benzyl ester p-toluenesulfonate salt

: 72-18-4
L-valine

Conditions

Conditions	Yield
With hydrogenchloride Heating;	70%

: 67-56-1
methanol

: L-Tyrosyl-L-valine

A: 538-86-3
benzyl methyl ether

B: 72-18-4
L-valine

Conditions

Conditions	Yield
With potassium hydroxide; [bis(acetoxy)iodo]benzene at 0 - 5℃; for 1.5h;	A 65% B n/a

...Expand

: (3S)-1-[(R)-1-phenylethyl]-3-(propan-2-yl)-1,4-diazaspiro[4.5]decan-2-one

: 72-18-4
L-valine

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid In water; toluene at 110℃; for 44h; Inert atmosphere;	65%

: 155486-42-3
(1R,2R,3R,5R)-1-((S)-1-Cyano-2-methyl-propylamino)-5-isopropenyl-2-methyl-cyclohexane-1,3-dicarbonitrile

: 72-18-4
L-valine

Conditions

Conditions	Yield
With hydrogenchloride at 110℃; for 12h;	62%

: 56-40-6
L-Glycin

: 1676-85-3, 2816-12-8, 24601-74-9, 43089-05-0
L-Valin-N-carbonsaeureanhydrid

A: 72-18-4
L-valine

B: 686-43-1
valylglycine

C: 3918-94-3
Val-Val

D: 462-60-2
N-carbamoylglycine

E oligomers of val: oligomers of val

Conditions

Conditions	Yield
With water; potassium hydroxide; potassium borate buffer at 3℃; Product distribution; effect of use of various amino acid and NCA with various concentrations; effect of use various temp.; extent of hydrolysis;	A n/a B 57.4% C n/a D n/a E n/a

...Expand

: 3715-29-5
sodium 3-methyl-2-oxobutyrate

: 72-18-4
L-valine

Conditions

Conditions	Yield
With zinc(II) perchlorate; (R)-15-amino-methyl-14-hydroxy-5,5-dimethyl-2,8-dithia<9>(2,5)pyridinophane In methanol for 24h; Ambient temperature;	57%
With ammonium sulfate; NADP+-specific glutamate dehydrogenase from Pseudomonas putida, I406F mutant; NADPH In aq. phosphate buffer at 35℃; pH=7.5; Reagent/catalyst; Green chemistry; Enzymatic reaction; enantioselective reaction;

: 52-67-5
3,3-dimethyl-D-cysteine

A: 640-68-6
D-Val-OH

B: 72-18-4
L-valine

Conditions

Conditions	Yield
nickel In water for 1h; Product distribution; Ambient temperature; further amounts of catalyst;	A 45% B n/a

: 4289-97-8, 44898-49-9, 4289-96-7
N-formylvaline

: 72-18-4
L-valine

Conditions

Conditions	Yield
With methanol; brucine ueber mehrere Stufen;

: 2901-80-6
N-benzoyl-D,L-valine

: 72-18-4
L-valine

Conditions

Conditions	Yield
mit Hilfe eines Enzym-Praeparats aus Pseudomonas;

: 2901-80-6
N-benzoyl-D,L-valine

A: 72-18-4
L-valine

B: 2901-80-6, 5699-79-6, 80394-38-3
(2R)-2-(benzoylamino)-3-methylbutyric acid

Conditions

Conditions	Yield
With soil bacteria

: 25692-88-0
Nα-[2-(4-biphenylyl)-2-propyloxycarbonyl]-L-valine

: 72-18-4
L-valine

Conditions

Conditions	Yield
With acetic acid at 22 - 25℃; Rate constant; other reaction partners;

: 75-30-9
2-iodo-propane

: 6456-74-2
Glycine tert-butyl ester

A: 640-68-6
D-Val-OH

B: 72-18-4
L-valine

Conditions

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 78-82-0
Isobutyronitrile

: 72-18-4
L-valine

Conditions

Conditions	Yield
With perchloric acid; N,N-Dichlorobenzenesulfonamide In methanol; water at 29.9℃; Equilibrium constant;

: 67-56-1
methanol

: 72-18-4
L-valine

: 6306-52-1
L-valine methylester hydrochloride

Conditions

Conditions	Yield
With thionyl chloride at 0 - 20℃;	100%
With thionyl chloride at 20℃; Cooling with ice; Inert atmosphere;	100%
Stage #1: L-valine With thionyl chloride at 0℃; for 4.16667h; Reflux; Stage #2: methanol	100%

: 85-44-9
phthalic anhydride

: 72-18-4
L-valine

: 6306-54-3
N-phthaloyl L-valine

Conditions

Conditions	Yield
at 135℃;	100%
at 140℃; for 0.166667h;	98%
In melt at 140℃; for 0.25h;	98%

: 72-18-4
L-valine

: 501-53-1
benzyl chloroformate

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water Inert atmosphere;	100%
With sodium hydroxide In water at 0 - 20℃;	100%
With potassium carbonate In water at 0 - 2℃; pH=1.5 - Ca. 2; Reagent/catalyst; pH-value; Temperature; Solvent;	99%

: 75-44-5
phosgene

: 72-18-4
L-valine

: 24601-74-9
(S)-4-isopropyloxazolidine-2,5-dione

Conditions

Conditions	Yield
In tetrahydrofuran at 40℃; for 1.5h;	100%
In tetrahydrofuran at 40℃; for 5h;	99.7%
In tetrahydrofuran; toluene at 50 - 60℃; for 4h;	96%

: 64-17-5
ethanol

: 72-18-4
L-valine

: 17431-03-7
L-valine ethyl ester

Conditions

Conditions	Yield
With thionyl chloride at -10℃; Heating / reflux;	100%
With thionyl chloride at -10℃; Heating / reflux;	100%
With hydrogenchloride for 12h; Reflux;	81.5%

: 72-18-4
L-valine

: 24424-99-5
di-tert-butyl dicarbonate

: 13734-41-3
t-Boc-L-valine

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane; water	100%
With sodium hydroxide In 1,4-dioxane; water at 0℃;	100%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 16h;	100%

: 72-18-4
L-valine

: 78-83-1
2-methyl-propan-1-ol

: 104-15-4
toluene-4-sulfonic acid

: 13018-45-6
(S)-1-isobutoxy-3-methyl-1-oxobutan-2-aminium 4-methylbenzenesulfonate

Conditions

Conditions	Yield
In water; toluene for 24h; Reflux; Dean-Stark;	100%
In benzene Heating;	84%
In benzene Heating;

...Expand

: 72-18-4
L-valine

: 1885-14-9
phenyl chloroformate

: 126147-70-4
(2S)-3-Methyl-2-(phenoxycarbonyl)aminobutyric acid

Conditions

Conditions	Yield
With sodium hydroxide; potassium hydrogencarbonate for 1.5h; Ambient temperature;	100%
With aluminum oxide; lithium chloride; lithium hydroxide In water at -20 - -10℃; for 5h; pH=9.5 - 10.2; Schotten-Baumann Reaction; Inert atmosphere;	92%
Stage #1: L-valine; phenyl chloroformate With sodium hydroxide In water at 0℃; for 5h; Stage #2: With hydrogenchloride In water pH=2;	75.9%

: 72-18-4
L-valine

: 2937-50-0
Allyl chloroformate

: 115491-96-8
N-allyloxycarbonyl-(L)-valine

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water at 20℃; for 18h;	100%
With potassium carbonate In tetrahydrofuran; water at 20℃; for 18h;	100%
With potassium carbonate In tetrahydrofuran; water at 20℃; for 18h;	100%

: 72-18-4
L-valine

: 40224-47-3
azidovaline

Conditions

Conditions	Yield
With imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate In methanol at 20℃; for 18h;	100%
With imidazole-1-sulfonyl azide hydrochloride; potassium carbonate; copper(II) sulfate In methanol at 20℃;	100%
With sodium azide; copper(ll) sulfate pentahydrate; trifluoromethylsulfonic anhydride; potassium carbonate In methanol; dichloromethane; water	97%

: 72-18-4
L-valine

: 5159-41-1
2-iodobenzyl alcohol

: 219645-03-1
N-(2'-hydroxymethylphenyl)-L-valine

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate In dimethyl sulfoxide at 90℃; for 48h;	100%
With copper(l) iodide; 2,4-dichlorophenoxyacetic acid dimethylamine; potassium carbonate at 90℃; for 48h;	86%
With water; potassium carbonate; copper(l) iodide In N,N-dimethyl acetamide at 90℃; for 48h;	81%

: 72-18-4
L-valine

: 107-13-1
acrylonitrile

: 91384-08-6
[N,N-Bis(2-cyanoethyl)]-L-valine

Conditions

Conditions	Yield
With sodium hydroxide; water at 100℃; for 24h; Alkylation;	100%

: 2-[tris(perfluorodecyl)silyl]ethoxycarbonyl-O-succimide

: 72-18-4
L-valine

: N-FTeoc-valine

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran; water at 20℃; for 2h;	100%

: 72-18-4
L-valine

: 60702-69-4
2-chloro-4-fluorobenzonitrile

: N-(3-chloro-4-cyanophenyl)valine

Conditions

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 90℃;	100%

: 72-18-4
L-valine

: 879-18-5
naphthalene-1-carbonic acid chloride

: 215096-58-5
N-(1-naphthoyl)-L-valine

Conditions

Conditions	Yield
Stage #1: L-valine With sodium hydroxide In water at 0℃; for 1h; Inert atmosphere; Stage #2: naphthalene-1-carbonic acid chloride In tetrahydrofuran; water at 20℃; Inert atmosphere;	100%

: 72-18-4
L-valine

: 1207290-13-8
C13H13FO

: 1493778-21-4
methyl (S)-2-((4-fluoro-2-(hex-1-ynyl)benzylidene)amino)-3-methylbutanoate

Conditions

Conditions	Yield
In dichloromethane at 20℃; Molecular sieve;	100%

: 59985-82-9
5-phenylisoxazole-3-carbaldehyde

: 72-18-4
L-valine

: C15H15N2O3(1-)*Li(1+)

Conditions

Conditions	Yield
With lithium hydride In methanol Reflux;	100%

: 59985-82-9
5-phenylisoxazole-3-carbaldehyde

: 72-18-4
L-valine

: C15H15N2O3(1-)*Na(1+)

Conditions

Conditions	Yield
With sodium methylate In methanol Reflux;	100%

: 59985-82-9
5-phenylisoxazole-3-carbaldehyde

: 72-18-4
L-valine

: 2C15H15N2O3(1-)*Ca(2+)

Conditions

Conditions	Yield
With calcium hydride In methanol Reflux;	100%

: 72-18-4
L-valine

: 640292-02-0
5-(4-methylphenyl)-1,2-oxazole-3-carbaldehyde

: C16H17N2O3(1-)*Li(1+)

Conditions

Conditions	Yield
With lithium hydride In methanol Reflux;	100%

: 72-18-4
L-valine

: 640292-02-0
5-(4-methylphenyl)-1,2-oxazole-3-carbaldehyde

: C16H17N2O3(1-)*Na(1+)

Conditions

Conditions	Yield
With sodium methylate In methanol Reflux;	100%

: 72-18-4
L-valine

: 640292-02-0
5-(4-methylphenyl)-1,2-oxazole-3-carbaldehyde

: 2C16H17N2O3(1-)*Ca(2+)

Conditions

Conditions	Yield
With calcium hydride In methanol Reflux;	100%

: 72-18-4
L-valine

: 2052-49-5
tetra(n-butyl)ammonium hydroxide

: (Sa)-3,3'-diformyl-2,2'-dihydroxy-1,1'-binaphthalene

: C32H30N2O6(2-)*2C16H36N(1+)

Conditions

Conditions	Yield
In methanol at 0℃; for 12h;	100%

...Expand

: 72-18-4
L-valine

: 104-15-4
toluene-4-sulfonic acid

: 873-76-7
para-Chlorobenzyl alcohol

: (S)-1-((4-chlorobenzyl)oxy)-3-methyl-1-oxobutan-2-aminium 4-methylbenzenesulfonate

Conditions

Conditions	Yield
In water; toluene for 24h; Reflux; Dean-Stark;	100%

...Expand

: 627-27-0
homoalylic alcohol

: 72-18-4
L-valine

: 104-15-4
toluene-4-sulfonic acid

: (S)-1-(but-3-en-1-yloxy)-3-methyl-1-oxobutan-2-aminium 4-methylbenzenesulfonate

Conditions

Conditions	Yield
In water; toluene for 24h; Reflux; Dean-Stark;	100%

...Expand

: 72-18-4
L-valine

: 17720-18-2
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate

: 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate (S)-2-ammonio-3-methylbutanoate

Conditions

Conditions	Yield
In water pH=5.67; Cooling with ice;	100%

: 72-18-4
L-valine

: nicotinic acid riboside 5'-monophosphate

: 73-22-3
L-Tryptophan

: (S)-1-carboxy-2-(1H-indol-3-yl)ethan-1-aminium (S)-1-carboxy-2-methylpropan-1-aminium 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonatooxy)methyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate

Conditions

Conditions	Yield
In water pH=2.24 - 2.49; Inert atmosphere; Cooling with ice;	100%

...Expand

L-Valine Consensus Reports

Reported in EPA TSCA Inventory.

L-Valine Specification

1. Introduction of L-Valine

L-Valine, with the IUPAC Name of (2S)-2-amino-3-methylbutanoic acid, is one kind of white crystalline powder. This belongs to the Product Categories which include Amino Acids;Amino Acid Derivatives;Valine [Val, V];Amino Acids and Derivatives;alpha-Amino Acids;Biochemistry;Nutritional Supplements;Amino Acids.

2. Properties of L-Valine

L-Valine has the following datas: (1)Index of Refraction: 1.461; (2)Molar Refractivity: 30.23 cm3; (3)Molar Volume: 110.1 cm3; (4)Polarizability: 11.98×10-24cm3; (5)Surface Tension: 39.8 dyne/cm; (6)Density: 1.063 g/cm3; (7)Flash Point: 83 °C; (8)Enthalpy of Vaporization: 49.58 kJ/mol; (9)Melting Point: 295-300 °C (subl.)(lit.); (10)Boiling Point: 213.6 °C at 760 mmHg; (11)Vapour Pressure: 0.0633 mmHg at 25°C; (12)Water Solubility: 85 g/L (20 oC).

3. Structure Descriptors of L-Valine

You could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC(C)C(C(=O)O)N
(2)Isomeric SMILES: CC(C)[C@@H](C(=O)O)N
(3)InChI: InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1
(4)InChIKey: KZSNJWFQEVHDMF-BYPYZUCNSA-N

4. Toxicity of L-Valine

1.		oms-omi 10 mmol/L		CBINA8 Chemico-Biological Interactions. 16 (1977),201.
2.		ipr-rat LD50:5390 mg/kg ABBIA4 58,253,55

5. Safety Information of L-Valine
Hazard Codes: Harmful

Xn
Risk Statements: 40
R40:Limited evidence of a carcinogenic effect.
Safety Statements: 24/25-36-22
S24/25:Avoid contact with skin and eyes.
S36:Wear suitable protective clothing.
S22:Do not breathe dust.
WGK Germany: 3
RTECS: YV9361000
HS Code: 29224995
Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.

6. Production of L-Valine

Racemic valine can be synthesized by bromination of isovaleric acid followed by amination of the α-bromo derivative
HO₂CCH₂CH(CH₃)₂ + Br₂ → HO₂CCHBrCH(CH₃)₂+ HBr
HO₂CCHBrCH(CH₃)₂+ 2 NH₃ → HO₂CCH(NH₂)CH(CH3)₂+ NH₄Br

Product Name

L-Valine

Synthetic route

L-Valine Consensus Reports

L-Valine Specification

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