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Threonine

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Identification
Molecular formula
C4H9NO3
CAS number
72-19-5
IUPAC name
(2S,3R)-2-amino-3-hydroxy-butanoic acid
State
State

At room temperature, threonine is a crystalline solid. It is naturally occurring and considered essential in the human diet.

Melting point (Celsius)
256.00
Melting point (Kelvin)
529.15
Boiling point (Celsius)
368.00
Boiling point (Kelvin)
641.15
General information
Molecular weight
119.12g/mol
Molar mass
119.1190g/mol
Density
1.6710g/cm3
Appearence

Threonine typically appears as a white crystalline solid. It is often available in the form of free-flowing powder. Its appearance can vary slightly depending on the exact form or hydration state.

Comment on solubility

Solubility of (2S,3R)-2-amino-3-hydroxy-butanoic acid (C4H9NO3)

(2S,3R)-2-amino-3-hydroxy-butanoic acid, commonly referred to as an amino acid derivative, exhibits interesting solubility characteristics. This compound is known to be highly soluble in water due to the presence of both an amino group (-NH2) and a hydroxyl group (-OH) in its structure. The solubility can be attributed to the following factors:

  • Hydrogen Bonding: The functional groups participate in hydrogen bonding with water molecules, enhancing the solubility.
  • Polarity: Its polar nature allows it to interact favorably with the polar solvent, water.
  • Ionization: In aqueous solutions, the amino acid can ionize, leading to an increased solubility in the form of charged species.

Consequently, one could state that the solubility of this compound is significantly influenced by its ability to form **hydrogen bonds** and its **ionic nature** in solution.

Moreover, the solubility varies with temperature:

  • Increased Temperature: Generally, the solubility of many amino acids increases with rising temperature.
  • pH Dependence: The solubility can also be affected by pH levels, as amino acids can exist in different ionic forms depending on the acidity/basicity of the solution.

In conclusion, the inherent chemical structure of (2S,3R)-2-amino-3-hydroxy-butanoic acid promotes a high solubility profile, making it readily available for biological and chemical applications.

Interesting facts

Interesting Facts about (2S,3R)-2-amino-3-hydroxy-butanoic acid

(2S,3R)-2-amino-3-hydroxy-butanoic acid, commonly known as threonine, is one of the essential amino acids that plays a pivotal role in various biological processes. As an essential amino acid, it cannot be synthesized by the human body and must be obtained through dietary sources, making it crucial for nutrition.

Biological Importance

Threonine is integral in several important biological functions including:

  • Protein synthesis: It is a key building block for proteins, enabling the formation of various enzymes and structural proteins.
  • Immune function: Threonine contributes to the production of antibodies, thus supporting the immune system.
  • Collagen and elastin: It plays a significant role in the synthesis of collagen and elastin, which are vital for maintaining skin health and elasticity.

Dietary Sources

Threonine is abundant in many protein-rich foods, including:

  • Meat (such as chicken and beef)
  • Dairy products
  • Eggs
  • Legumes (like lentils and beans)
  • Nuts and seeds

Physiological Effects

Research has shown that threonine can:

  • Enhance the immune response in athletes and those under physical stress.
  • Help in alleviating symptoms of metabolic disorders.
  • Support digestive health by promoting mucus production in the intestines.

As an interesting note, threonine is involved in the synthesis of the neurotransmitter serotonin, which plays a vital role in mood regulation. Its presence in the diet is essential not just for physical health, but also for mental well-being.

In summary, the study of (2S,3R)-2-amino-3-hydroxy-butanoic acid reveals its dual significance in nutrition and biochemistry. Understanding its roles could lead to advancements in health, dietary recommendations, and even pharmacological applications.

Synonyms
L-threonine
threonine
72-19-5
(2S,3R)-2-amino-3-hydroxybutanoic acid
DL-Threonine
Threonin
L-(-)-Threonine
(S)-Threonine
H-Thr-OH
2-amino-3-hydroxybutyric acid
80-68-2
Treonina
Threonine, L-
Threonine (VAN)
Threoninum [Latin]
Treonina [Spanish]
thre
Threoninum
(2S,3R)-2-Amino-3-hydroxybutyric acid
Threonine [USAN:INN]
(2S)-threonine
(2S,3R)-(-)-Threonine
L-Threonin
L-thr
EINECS 200-774-1
Threonine, DL-
MFCD00064270
NSC 16589
NSC 46701
L-alpha-Amino-beta-hydroxybutyric acid
2-Amino-3-hydroxybutanoic acid, (R-(R*,S*))-
DTXSID2046412
FEMA NO. 4710
UNII-2ZD004190S
CHEBI:16857
Butanoic acid, 2-amino-3-hydroxy-, (R-(R*,S*))-
HSDB 7797
L-2-Amino-3-hydroxybutyric acid
NSC-16589
NSC-46701
TFM6DU5S6A
2ZD004190S
H-DL-Thr-OH
DTXCID0026412
[R-(R*,S*)]-2-Amino-3-hydroxybutanoic acid
Threoninum (Latin)
THREONINE (II)
THREONINE [II]
THREONINE (L)
thr
(2S,3R)-rel-2-Amino-3-hydroxybutanoic acid
THREONINE (MART.)
THREONINE [MART.]
(R-(R*,S*))-2-Amino-3-hydroxybutanoic acid
THREONINE (EP MONOGRAPH)
THREONINE [EP MONOGRAPH]
Threonine #
THREONINE (USP MONOGRAPH)
THREONINE [USP MONOGRAPH]
Allothreonine, D-
CAS-72-19-5
(R-(R*,S*))-2-Amino-3-hydroxybutanoate
[R-(R*,S*)]-2-Amino-3-hydroxybutanoate
L-(U-14C)Threonine
NSC46701
beta-methylserine
MFCD00063722
NSC-206292
(+/-)-2-Amino-3-hydroxybutyric acid
NCGC00164520-01
NCGC00164520-02
Threonine (USP)
L-Threonine,(S)
H-Thr
(+/-)-threonine
L-Thr-OH
L-Threonine (9CI)
Threonine, labeled with carbon-14, L-
L-Threonine (Standard)
THREONINE [INN]
L-Threonine (JP18)
THREONINE [MI]
Threonine (L-Threonine)
THREONINE [HSDB]
THREONINE [USAN]
UNII-TFM6DU5S6A
THREONINE [VANDF]
Threonine, L- (8CI)
2-Amino-3-hydroxybutyrate
bmse000049
bmse000810
bmse000859
L-THREONINE [FCC]
L-THREONINE [JAN]
L-Threonine (H-Thr-OH)
2-Amino-3-hydroxybutanoate
SCHEMBL1480
THREONINE [WHO-DD]
L-2-Amino-3-hydroxybutyrate
L-THREONINE [USP-RS]
L-Threonine non-animal source
CCRIS 8603
CHEMBL291747
GTPL4785
CHEBI:26986
HY-N0658R
DTXSID70893087
L-alpha-Amino-beta-hydroxybutyrate
Pharmakon1600-01301008
HY-N0658
EINECS 201-300-6
Tox21_112154
AC7878
NSC760118
s4951
(2S,3R)-2-Amino-3-hydroxybutyrate
AKOS006240505
AKOS015840277
Tox21_112154_1
CCG-214540
CS-W020046
DB00156
FT03495
NSC 206292
NSC-760118
7013-32-3
AC-11296
AS-12789
L-Threonine, BioXtra, >=99.5% (NT)
L-Threonine, p.a., 99.0-101.0%
AI3-18477
DB-029984
(2S,3R)-rel-2-Amino-3-hydroxybutanoicacid
[R-(R*,S*)]-2-amino-3-hydroxy-Butanoate
NS00001961
NS00078877
T0230
EN300-54609
L-Threonine, reagent grade, >=98% (HPLC)
C00188
D00041
G76695
M02962
SBI-0633502.0002
[R-(R*,S*)]-2-amino-3-hydroxy-Butanoic acid
Q186521
(2S,3R)-2-Amino-3-hydroxybutyric acid;H-Thr-OH
3DD2E9AD-DB9A-460E-8A6B-C01B0F67AC4E
BRD-K75508643-001-02-6
LYSINE HYDROCHLORIDE IMPURITY C [EP IMPURITY]
48: PN: WO2004076659 FIGURE: 7 claimed sequence
F8881-8883
L-Threonine, certified reference material, TraceCERT(R)
Z813019058
L-Threonine, European Pharmacopoeia (EP) Reference Standard
L-Threonine, United States Pharmacopeia (USP) Reference Standard
L-Threonine, Pharmaceutical Secondary Standard; Certified Reference Material
200-774-1
L-Threonine, from non-animal source, meets EP, JP, USP testing specifications, suitable for cell culture, 99.0-101.0%