80-68-2

Basic information

• Product Name: DL-Threonine
• Synonyms: H-DL-THR-OH;DL-AMINO-HYDROXYBUTYRIC ACID;DL-ALPHA-AMINO-BETA-HYDROXYBUTYRIC ACID;DL-THREONINE;DL-2-AMINO-3-HYDROXYBUTANOIC ACID;DL-2-AMINO-3-HYDROXYBUTYRIC ACID;ALPHA-AMINO-BETA-HYDROXYBUTYRIC ACID;(+/-)-2-AMINO-3-HYDROXYBUTYRIC ACID
• CAS NO: 80-68-2
• Molecular Formula: C₄H₉NO₃
• Molecular Weight: 119.12
• EINECS: 201-300-6
• Product Categories: Amino Acids;Amino Acid Derivatives;Threonine [Thr, T];alpha-Amino Acids;Biochemistry;Amino Acids;amino acid
• Mol File: 80-68-2.mol

Chemical Properties

• Melting Point: 244 °C (dec.)(lit.)
• Boiling Point: 222.38°C (rough estimate)
• Flash Point: 162.9 °C
• Appearance: White/Powder
• Density: 1.3126 (rough estimate)
• Vapor Pressure: 3.77E-06mmHg at 25°C
• Refractive Index: 1.4183 (estimate)
• Storage Temp.: Store at RT.
• PKA: 2.09(at 25℃)
• Water Solubility: 200 g/L (25 ºC)
• Merck: 14,9380
• BRN: 1721647
• CAS DataBase Reference: DL-Threonine(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Threonine(80-68-2)
• EPA Substance Registry System: DL-Threonine(80-68-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-37/39-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 80-68-2(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Research:
DL-Threonine is used as a polar essential amino acid for biochemical research, serving as a precursor of glycine and used in the biosynthesis of proteins.
Used in Nutrition Enhancement:
DL-Threonine is used as a nutrition enhancer, playing a key role in regulating levels of other amino acids and supporting muscle tissue maintenance and growth.
Used in Animal Feed Industry:
DL-Threonine is used as an additive to animal feed, improving the health or production of animals by providing an essential amino acid that cannot be synthesized de novo in higher animals.
Used in Agriculture:
DL-Threonine is used in agriculture as a chelator of metal cations to improve the absorption of minerals from supplements and fertilizers, enhancing plant growth and health.
Used in Food Industry:
DL-Threonine can be co-used with other amino acids in various cereals, such as rice, wheat flour, barley, oats, and corn, to improve the nutritional value and enhance the flavor of the food products.
Used in Pharmaceutical Industry:
DL-Threonine can be used for the separation to obtain L-threonine, which is further used in the preparation of amino acid infusions and integrated amino acid preparations for medical purposes.
Occurrence:
Foods high in threonine include cottage cheese, poultry, fish, meat, lentils, black turtle beans, and sesame seeds.

Content analysis

It is the same as the content analysis method of "DL-alanine". Every mL of 0.1mol/L perchloric acid solution is equivalent to 11.91 mg of DL-threonine (C4H9NO3).

Toxicity

L-type: LD50: 26mmol/kg (rat, intraperitoneal injection); D-type: LD50 45mmol/kg (rat, intraperitoneal injection). It can be safely applied to food products (FDA, §172.320, 2000).

History

Threonine was discovered as the last of the 20 common proteinogenic amino acids in the 1930s by William Cumming Rose.

Biosynthesis

As an essential amino acid, threonine is not synthesized in humans, hence we must ingest threonine in the form of threoninecontaining proteins. In plants and microorganisms, threonine is synthesized from aspartic acid via α-aspartyl-semialdehyde and homoserine. Homoserine undergoes O-phosphorylation; this phosphate ester undergoes hydrolysis concomitant with relocation of the OH group. Enzymes involved in a typical biosynthesis of threonine include : aspartokinase β-aspartate semialdehyde dehydrogenase homoserine dehydrogenase homoserine kinase threonine synthase.

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 1031, 1991 DOI: 10.1016/S0040-4039(00)74479-0The Journal of Organic Chemistry, 63, p. 3499, 1998 DOI: 10.1021/jo9722717

Metabolism

Threonine is metabolized in two ways: It is converted to pyruvate via threonine dehydrogenase. An intermediate in this pathway can undergo thiolysis with CoA to produce acetyl-CoA and glycine. In humans, it is converted to α-ketobutyrate in a less common pathway via the enzyme serine dehydratase, and thereby enters the pathway leading to succinyl-CoA..

Stereoisomerism

Threonine is one of two proteinogenic amino acids with two chiral centers. Threonine can exist in four possible stereo isomers with the following configurations: (2S,3R), (2R,3S), (2S,3S) and (2R,3R). However, the name L-threonine is used for one single diastereomer, (2S,3R)-2-amino-3-hydroxybutanoic acid. The second stereoisomer (2S,3S), which is rarely present in nature, is called L-allo-threonine. The two stereo isomers (2R,3S)- and (2R,3R)-2-amino-3-hydroxy butanoic acid are only of minor importance.

InChI:InChI=1/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)

Upstream product

• 72-19-5 rac-allo-threonine 
• 855223-97-1 N-methyl-threonine 
• 876367-23-6 2-Dibenzylamino-3-hydroxy-butyric acid 
• 75-07-0 acetaldehyde 
• 56-40-6 glycine 
• 7732-18-5 water 
• 66-72-8 pyridoxal 
• 5431-93-6 ethyl 2-(acetylamino)-3-oxobutanoate 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 66508-93-8 ethyl 2-(hydroxyimino)-3-oxybutyrate 
• 108-24-7 acetic anhydride 
• 67-56-1 methanol 
• 5428-45-5 (+/-)-erythro-2-bromo-3-methoxy-butyric acid anilide 

Downstream Products

• 39994-75-7 (+/-) threonine methyl ester hydrochloride 
• 24809-87-8 N-carbamoyl-threonine 
• 75-07-0 acetaldehyde 
• 64-19-7 acetic acid 
• 107-92-6 butyric acid 
• 56-40-6 glycine 
• 7537-02-2 threonine TMS 
• 56884-52-7 1-[6-anilino-5-hydroxy-2-(1-hydroxy-ethyl)-benzooxazol-4-yl]-ethanone 
• 3309-49-7 Cyclohexyloxycarbonyl-DL-threonin 
• 13881-40-8 2-Brom-3-hydroxy-buttersaeure 
• 3913-65-3 2-hydroxypropanal 
• 72-19-5 L-threonine 
• 72-19-5 D-threonine 
• 138-15-8 l-glutamic acid hydrochloride 

Relevant articles and documents

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