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72-19-5

Basic Information
CAS No.: 72-19-5
Name: L-Threonine
Molecular Structure:
Molecular Structure of 72-19-5 (L-Threonine)
Formula: C4H9NO3
Molecular Weight: 119.12
Synonyms: Butanoic acid, 2-amino-3-hydroxy-, (R-(R*,S*))-;Thr;Threonine [USAN:INN];L-Threonin;(2S,3R)-2-azaniumyl-3-hydroxy-butanoate;Treonina [Spanish];(2R,3R)-2-amino-3-hydroxy-butanoic acid;Threonine, L-;(2S,3R)-2-Amino-3-hydroxybutyric acid;Valine,3-hydroxy-;L-alpha-Amino-beta-hydroxybutyric acid;(2S,3S)-2-azaniumyl-3-hydroxy-butanoate;(2S)-threonine;Threoninum [Latin];Threonine (VAN);L-2-Amino-3-hydroxybutyric acid;L-Threonine(Feed Grade);L-Thr-OH;L-Threonine Aji97;Threonine, L- (8CI);(2S,3R)-2-amino-3-hydroxy-butanoic acid;L-(-)-Threonine;Threonin;[R-(R*,S*)]-2-Amino-3-hydroxybutanoic acid;L-Threonine (9CI);Threonine (USP);
EINECS: 200-774-1
Density: 1.307 g/cm3
Melting Point: 256 °C (dec.)(lit.)
Boiling Point: 345.803 °C at 760 mmHg
Flash Point: 162.936 °C
Solubility: 90 g/L (20 °C) in water
Appearance: White crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-37/39-26
Transport Information:
PSA: 83.55000
LogP: -0.52060
Synthetic route
111-26-2

hexan-1-amine

(S)-2-(3,5-Dinitro-4-oxo-4H-pyridin-1-yl)-3-hydroxy-butyric acid

A

72-19-5

L-threonine

B

74197-48-1

1-hexyl-3,5-dinitro-4-pyridone

Conditions
ConditionsYield
In pyridine Product distribution;A 83.8%
B n/a
Conditions
ConditionsYield
With hydrogen; acetic acid; palladium on activated charcoal for 48h; other (protected) amino acids; other alcohol;A n/a
B 40%
C n/a
75-07-0

acetaldehyde

56-40-6

glycine

72-19-5

L-threonine

Conditions
ConditionsYield
With pyridoxal 5'-phosphate; L-threonine aldolase In phosphate buffer at 25℃; for 3h;

antimycin B1

72-19-5

L-threonine

Conditions
ConditionsYield
With hydrogenchloride; water at 110℃; for 20h;

ucb K115

72-19-5

L-threonine

Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate; cobalt(II) sulphate heptahydrate; N-succinyl L-amino acid desuccinylase from Burkholderia ambifaria AMMD; N-succinyll-amino acid β-hydroxylase from Burkholderia ambifaria AMMD; ascorbic acid In aq. phosphate buffer at 30℃; for 24h; Enzymatic reaction;
Conditions
ConditionsYield
With thionyl chloride at 0℃; for 3.25h; Reflux;100%
72-19-5

L-threonine

79-22-1

methyl chloroformate

(2S,3R)-3-hydroxy-2-((methoxycarbonyl)amino)butanoic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; sodium carbonate In methanol; dichloromethane98%
With sodium hydrogencarbonate In diethyl ether; water

[Pd(acetylacetonato-O,O')((1R,2R)-(PPh2NH)2C6H10)](ClO4)

72-19-5

L-threonine

[Pd(L-threoninate-κ-N,O)((1R,2R)-(PPh2NH)2C6H10)](ClO4)

Conditions
ConditionsYield
In methanol byproducts: acetylacetone; to a soln. of complex in methanol was added amino acid, the mixt. was refluxed for 3 h, cooled; evapd. to dryness, treated with diethyl ether, the solid was filtered, washed with diethyl ether, air-dried;85%
72-19-5

L-threonine

104-15-4

toluene-4-sulfonic acid

107-18-6

allyl alcohol

88224-11-7

L-Threonin-allylester-hydro-p-toluolsulfonat

Conditions
ConditionsYield
In benzene Heating;84%
7647-01-0

hydrogenchloride

16940-66-2

sodium tetrahydroborate

12093-10-6

ferrocenecarboxaldehyde

72-19-5

L-threonine

H(S-fThr)

Conditions
ConditionsYield
With LiOH*H2O In methanol L-threonine and LiOH*H2O in dry MeOH stirred for 30 min; MeOH soln. of Fe complex added dropwise; stirred for 20 min; treated with NaBH4 with stirring; solvent evapd.; dissolved in H2O; acidified with dilute HCl (pH 5-7); filtered; ppt. washed with H2O; dried in vac. desiccator; elem. anal.;84%
72-19-5

L-threonine

74197-40-3

3,5-dinitro-1-(4-nitrophenyl)-4-pyridone

A

100-01-6

4-nitro-aniline

B

(S)-2-(3,5-Dinitro-4-oxo-4H-pyridin-1-yl)-3-hydroxy-butyric acid

Conditions
ConditionsYield
In pyridine; water for 3h; Ambient temperature;A n/a
B 75%

Field-Durant Green

64-17-5

ethanol

72-19-5

L-threonine

90-02-8

salicylaldehyde

potassium Δ-bis(N-salicylidene-(S)-threoninato)cobaltate*2(ethanol)

Conditions
ConditionsYield
In ethanol salicylaldehyde added with stirring to mixt. of Co complex and amino acid in EtOH; refluxed for 3 h; filtered; filtrate concd. in vac.; residue washed with Et2O; dissolved in EtOH; column chromd. (Al2O3, EtOH); purified by gel chromy. (Sephadex LH-20, EtOH-benzene 1:3); elem. anal.;70%

sodium tris(carbonato)cobaltate(III)

72-19-5

L-threonine

90-02-8

salicylaldehyde

lithium δ-bis[N-salicylidene-(S)-threoninato]cobaltate dihydrate

Conditions
ConditionsYield
In ethanol aldehyde was added with stirring to mixt. of Co complex and amino acid in EtOH; refluxed for 3 h; filtered; evapd. (vac.); washed (Et2O); dissolved in EtOH; chromd. (Al2O3, EtOH); chromd. (gel, EtOH/C6H6, 1/3); dissolved in aq. EtOH; passed through ion-exchange resin; evapd. (vac.); chromd. (gel, EtOH/C6H6, 1/3);elem. anal.;70%
1445-73-4

1-Methyl-4-piperidone

72-19-5

L-threonine

119072-54-7, 2769-71-3

2,6-dimethylphenyl isonitrile

4-(2,6-dimethylphenyl)-2-ethyl-9-methyl-1,4,9-triazaspiro[5.5]undec-1-ene-3,5-dione

Conditions
ConditionsYield
With triethylamine In 2,2,2-trifluoroethanol at 100℃; for 24h;70%

sodium tris(carbonato)cobaltate(III)

72-19-5

L-threonine

1259524-22-5

3-allyl-5-bromosalicylaldehyde

lithium λ-bis[N-(3-allyl-5-bromosalicylidene)-(S)-threoninato]cobaltate dihydrate

lithium δ-bis[N-(3-allyl-5-bromosalicylidene)-(S)-threoninato]cobaltate dihydrate

Conditions
ConditionsYield
In ethanol aldehyde was added with stirring to mixt. of Co complex and amino acid in EtOH; refluxed for 3 h; filtered; evapd. (vac.); washed (Et2O); dissolved in EtOH; chromd. (Al2O3, EtOH); chromd. (gel, EtOH/C6H6, 1/3); dissolved in aq. EtOH; passed through ion-exchange resin; evapd. (vac.); chromd. (gel, EtOH/C6H6, 1/3);elem. anal.;A 22%
B 65%
72-19-5

L-threonine

71942-48-8

6-nitro-2-oxo-2H-chromene-3-carbonyl chloride

80613-36-1

6-nitrocoumarin-3-CO-L-Thr

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane 1) room temperature, 2) 2 h, reflux;54%

(η6-fluorobenzene)(η5-cyclopentadienyl) iron(II) hexafluorophosphate

72-19-5

L-threonine

[(η-C6H5NHCH(CH(OH)Me)COOH)(η-C5H5)Fe][PF6]

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide 120-130°C, 1.0 h; cooling, filtration into ether (sepn. of oil), decantation, washing (ether), extn. into Me2CO, filtration, chromy. (Al2O3, Me2CO, then MeOH/H2O=5:1), evapn. (reduced pressure, 60-70°C);40%

nickel(II) perchlorate hexahydrate

lanthanum(III) perchlorate hexahydrate

72-19-5

L-threonine

[LaNi6(L-threonine(-H)(1-))12](ClO4)3(H2O)15

Conditions
ConditionsYield
With NaOH In water stoichiometric equiv. of Ni(ClO4)2*6H2O and L-threonine added to aq. soln. of La(ClO4)3*6H2O; pH adjusted to 6.6 by slow addition of NaOH aq. soln.; stirred for 2 h; filtered to remove precipitates formed; placed in a desiccator filled with P2O5 for 1 month; elem. anal.;35%

{CoBr2(C8H12(C2H5)4(NH)4)}(1+)*Br(1-)={CoBr2(C8H12(C2H5)4(NH)4)}Br

72-19-5

L-threonine

sodium perchlorate

{Co(OCOCH(NH2)CH(OH)CH3)(C8H12(C2H5)4(NH)4)}(2+)*2{ClO4}(1-)*3H2O

Conditions
ConditionsYield
With NaOH In water adjusting the pH of an aq. soln. of the CoBr2 complex and (S)-thr to 8.0 with NaOH, evapn. to near dryness (after 1 h), addn. of a slight excess of an aq. NaClO4 soln., crystn.; elem. anal.;30%
72-19-5

L-threonine

501-53-1

benzyl chloroformate

19728-63-3

N-[(phenylmethoxy)carbonyl]-L-threonine

Conditions
ConditionsYield
With sodium hydrogencarbonate
492-61-5

β-D-glucose

72-19-5

L-threonine

A

320-77-4

1-hydroxy-propane-1,2,3-tricarboxylic acid

B

2-methylisocitric acid

C

77-92-9

citric acid

Conditions
ConditionsYield
With Saccharomycopsis lipolytica In water at 26℃; for 120h; Product distribution; also in n-hexadecane medium; catabolism of amino acids by S. lipolytica;
66065-85-8

succinimidyl 2,2,2-trichloroethyl carbonate

72-19-5

L-threonine

88050-12-8

N-(2,2,2-trichloroethoxycarbonyl)-threonine

Conditions
ConditionsYield
With sodium hydroxide; sodium hydrogencarbonate In 1,4-dioxane for 0.166667h; Ambient temperature;
72-19-5

L-threonine

17350-66-2

N-benzyloxycarbonylalaninehydrazid

Conditions
ConditionsYield
With hydrogenchloride; tert.-butylnitrite; triethylamine 1. DMF, dioxane, -10 degC, 10 min, 2.) H2O, cold; Yield given. Multistep reaction;
72-19-5

L-threonine

86895-16-1

[(R)-1-[(S)-1-(Hydrazinocarbonylmethyl-carbamoyl)-ethylcarbamoyl]-2-(4-methoxy-benzylsulfanyl)-ethyl]-carbamic acid tert-butyl ester

86905-27-3

Boc-Cys(MBzl)-Ala-Gly-Thr-OH

Conditions
ConditionsYield
With hydrogenchloride; tert.-butylnitrite; triethylamine 1.)DMF, dioxane, -25 degC, 10 min, 2.) H2O, cold; Yield given. Multistep reaction;
72-19-5

L-threonine

24830-94-2

D-allo-threonine

Conditions
ConditionsYield
With hydrogenchloride; ethanethiol at 110℃; Rate constant; various times;
72-19-5

L-threonine

849704-22-9

(2S,3R)-2-chloro-3-hydroxybutanoic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite at -5℃; for 5h;
72-19-5

L-threonine

A

124-38-9

carbon dioxide

B

78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With hydrogenchloride; chloroamine-T In water at 29.9 - 44.9℃; Thermodynamic data; Rate constant; Ea, log A, -ΔS(excit.), ΔH(excit.), ΔG(excit.); further acid concentration, further acid and alkaline media;
72-19-5

L-threonine

C3H8NO

Conditions
ConditionsYield
With hydroxide In water Mechanism; Ambient temperature; Irradiation; examination of effect of protonation state of amino group;
72-19-5

L-threonine

75-64-9

tert-butylamine

88050-13-9

Troc-Thr-OH*t-C4H9NH2

Conditions
ConditionsYield
Yield given;
72-19-5

L-threonine

74-89-5

methylamine

79009-37-3

(S)-2-Amino-3-hydroxy-N-methyl-butyramide

Conditions
ConditionsYield
With thionyl chloride 1)r.t., methanol, 2) 40 deg C 30 min, water; Multistep reaction;
72-19-5

L-threonine

774-74-3

2-(2,4-dichlorophenoxy)acetyl chloride

N-(2,4-Dichlor-phenoxyacetyl)-L-threonin

Conditions
ConditionsYield
With hydroxide
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    L-Threonine

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    L-Threonine CAS# 72-19-5

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    L-Threonine

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Chemistry

Structure of L-Threonine (CAS NO.72-19-5):

IUPAC Name: (2S,3R)-2-amino-3-hydroxybutanoic acid 
Empirical Formula: C4H9NO3
Molecular Weight: 119.1192 
EINECS: 200-774-1 
Index of Refraction: 1.507
Molar Refractivity: 27.13 cm3
Molar Volume: 91.1 cm3
Polarizability: 10.75×10-24cm3
Surface Tension: 60 dyne/cm
Density: 1.307 g/cm3
Flash Point: 162.9 °C
Enthalpy of Vaporization: 68.32 kJ/mol 
Melting Point: 256 °C (dec.)(lit.)
Boiling Point: 345.8 °C at 760 mmHg
Vapour Pressure: 3.77E-06 mmHg at 25°C 
Storage temp: Store at RT. 
Water Solubility: 90 g/L (20 ºC) 
Stability: Stable. Incompatible with strong oxidizing agents. 
Physical Appearance: White crystalline powder
Product Categories: Miscellaneous Biochemicals;Amino Acid Derivatives;Threonine [Thr, T];Amino Acids and Derivatives;alpha-Amino Acids;Amino Acids;Biochemistry;Nutritional Supplements;L-Amino Acids;Amino Acids 
Synonyms of L-Threonine (CAS NO.72-19-5): (S)-Threonine ; 2-Amino-3-hydroxybutanoic acid, (R-(R*,S*))- ; Butanoic acid, 2-amino-3-hydroxy-, (R-(R*,S*))- ; Threonin ; Threonine ; Threoninum ; Treonina
Canonical SMILES: CC(C(C(=O)O)N)O
Isomeric SMILES: C[C@H]([C@@H](C(=O)O)N)O
InChI: InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1
InChIKey: AYFVYJQAPQTCCC-GBXIJSLDSA-N

Uses

 L-Threonine (CAS NO.72-19-5) is an essential amino acid, but not synthesized in humans.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 intraperitoneal 3098mg/kg (3098mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archives of Biochemistry and Biophysics. Vol. 58, Pg. 253, 1955.

Safety Profile

Hazard Codes: Xi
Risk Statements: 36/37/38: Irritating to eyes, respiratory system and skin 
Safety Statements: 24/25-37/39-26
24/25:  Avoid contact with skin and eyes 
37/39:  Wear suitable gloves and eye/face protection 
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
WGK Germany: 3
Hazard Note: Irritant
HS Code: 29225000

Specification

1. First Aid Measures of L-Threonine (CAS NO.72-19-5):
Ingestion: If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation: Remove from exposure to fresh air immediately. Get medical aid if cough or other symptoms appear.
Skin: Get medical aid if irritation develops or persists. Flush skin with plenty of soap and water.
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
2. Handling and Storage:
Storage: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Handling: Wash thoroughly after handling. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.