3-Guanidinopropionic acid
Synonym(s):β-Guanidinopropionic acid
- CAS NO.:353-09-3
- Empirical Formula: C4H9N3O2
- Molecular Weight: 131.13
- MDL number: MFCD00045939
- EINECS: 206-530-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-06 18:33:45
What is 3-Guanidinopropionic acid?
Description
Guanidinopropionic acid is a white crystal that dissolves in water and is a creatine analog. Guanidinopropionic acid is a kind of amino acid derivatives. It is an important chemical raw material and intermediate. It exists in the serum, brain, liver, kidney and urine of mammals. It can improve insulin sensitivity and selectively reduce Adipose tissue weight can treat and prevent metabolic disorders, hyperglycemia, hyperinsulinemia, insensitivity to blood insulin, hyperlipidemia, hyperamylase, obesity and other symptoms.
Chemical properties
White solid
The Uses of 3-Guanidinopropionic acid
3-Guanidinopropionic Acid is an acidic guanidine derivative that has been shown to ameliorate hyperglycemia in animal models of noninsulin-dependent diabetes.
What are the applications of Application
3-Guanidinopropionic acid is a creatine and GABA analog found in mammalian blood plasma and erythrocytes
Definition
ChEBI: 3-guanidinopropanoic acid is a guanidine compound bearing an N-(2-carboxyethyl) substituent. It is a creatine analogue that has been found to decreases plasma glucose levels It has a role as a hypoglycemic agent. It derives from a propionic acid. It is a tautomer of a 3-guanidinopropanoic acid zwitterion.
Synthesis
Using thiourea |?-alanine as a raw material, guanidinopropionic acid is prepared by a two-step alkylation reaction of nucleophilic substituted amine, the content is greater than 99.0%, and the total yield is 76.2%. The process is low cost, mild conditions, and easy operation, simple and suitable for industrial production.
References
[1] winder w w, hardie d g. amp-activated protein kinase, a metabolic master switch: possible roles in type 2 diabetes[j]. american journal of physiology-endocrinology and metabolism, 1999, 277(1): e1-e10.
[2] chaturvedi, r. k.,adhihetty, p.,shukla, s., et al. impaired pgc-1α function in muscle in huntington’s disease. human molecular genetics 18(16), 3048-3065 (2009).
[3] larsen s d, connell m a, cudahy m m, et al. synthesis and biological activity of analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid: discovery of a novel aminoguanidinoacetic acid antidiabetic agent[j]. journal of medicinal chemistry, 2001, 44(8): 1217-1230.
[4] meglasson m d, wilson j m, yu j h, et al. antihyperglycemic action of guanidinoalkanoic acids: 3-guanidinopropionic acid ameliorates hyperglycemia in diabetic kkay and c57bl6job/ob mice and increases glucose disappearance in rhesus monkeys[j]. journal of pharmacology and experimental therapeutics, 1993, 266(3): 1454-1462.
Properties of 3-Guanidinopropionic acid
Melting point: | 222 °C (dec.)(lit.) |
Boiling point: | 299.1±42.0 °C(Predicted) |
Density | 1.46±0.1 g/cm3(Predicted) |
storage temp. | Keep in dark place,Inert atmosphere,2-8°C |
solubility | Aqueous Acid (Slightly), Water (Slightly, Heated) |
form | Solid |
pka | 4.22±0.10(Predicted) |
color | White to Off-White |
BRN | 1705262 |
CAS DataBase Reference | 353-09-3(CAS DataBase Reference) |
Safety information for 3-Guanidinopropionic acid
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 3-Guanidinopropionic acid
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