Name: L-Valine
SKU: 72-18-4

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Basic Information

Molecular Structure:
CAS No.:	72-18-4
Name:	L-Valine
Article Data:	340

Formula:	C₅H₁₁NO₂
Molecular Weight:	117.148
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;
EINECS:	200-773-6
Density:	1.064 g/cm³
Melting Point:	295-300 °C (subl.)(lit.)
Boiling Point:	213.642 °C at 760 mmHg
Flash Point:	83.008 °C
Solubility:	85 g/L (20 °C) in water
Appearance:	White crystalline powder
Hazard Symbols:	Xn
Risk Codes:	40
Safety:	24/25-36-22
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%

Raw Materials

75-30-9

78-82-0

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Consensus Reports

Reported in EPA TSCA Inventory.

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

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Consensus Reports

Specification