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353-09-3

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353-09-3 Usage

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

Uses

3-Guanidinopropionic Acid is an acidic guanidine derivative that has been shown to ameliorate hyperglycemia in animal models of noninsulin-dependent diabetes.

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 β-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.

Check Digit Verification of cas no

The CAS Registry Mumber 353-09-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,5 and 3 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 353-09:
(5*3)+(4*5)+(3*3)+(2*0)+(1*9)=53
53 % 10 = 3
So 353-09-3 is a valid CAS Registry Number.
InChI:InChI=1/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7)

353-09-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-guanidinopropanoic acid

1.2 Other means of identification

Product number -
Other names 3-carbamimidamidopropanoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:353-09-3 SDS

353-09-3Relevant articles and documents

Structural and functional characterization of plant aminoaldehyde dehydrogenase from pisum sativum with a broad specificity for natural and synthetic aminoaldehydes

Tylichova, Martina,Kopecny, David,Morera, Solange,Briozzo, Pierre,Lenobel, Rene,Snegaroff, Jacques,Sebela, Marek

experimental part, p. 870 - 882 (2011/04/24)

Aminoaldehyde dehydrogenases (AMADHs, EC 1.2.1.19) belong to the large aldehyde dehydrogenase (ALDH) superfamily, namely, the ALDH9 family. They oxidize polyamine-derived ω-aminoaldehydes to the corresponding ω-amino acids. Here, we report the first X-ray structures of plant AMADHs: two isoenzymes, PsAMADH1 and PsAMADH2, from Pisum sativum in complex with β-nicotinamide adenine dinucleotide (NAD+) at 2.4 and 2.15 A resolution, respectively. Both recombinant proteins are dimeric and, similarly to other ALDHs, each monomer is composed of an oligomerization domain, a coenzyme binding domain and a catalytic domain. Each subunit binds NAD+ as a coenzyme, contains a solvent-accessible C-terminal peroxisomal targeting signal (type 1) and a cation bound in the cavity close to the NAD+ binding site. While the NAD+ binding mode is classical for PsAMADH2, that for PsAMADH1 is unusual among ALDHs. A glycerol molecule occupies the substrate binding site and mimics a bound substrate. Structural analysis and substrate specificity study of both isoenzymes in combination with data published previously on other ALDH9 family members show that the established categorization of such enzymes into distinct groups based on substrate specificity is no more appropriate, because many of them seem capable of oxidizing a large spectrum of aminoaldehyde substrates. PsAMADH1 and PsAMADH2 can oxidize N,N,N-trimethyl-4-aminobutyraldehyde into γ-butyrobetaine, which is the carnitine precursor in animal cells. This activity highly suggests that in addition to their contribution to the formation of compatible osmolytes such as glycine betaine, β-alanine betaine and γ-aminobutyric acid, AMADHs might participate in carnitine biosynthesis in plants.

Amidination of amines under microwave conditions using recyclable polymer-bound 1H-pyrazole-1-carboxamidine

Solodenko, Wladimir,Broeker, Patrick,Messinger, Josef,Schoen, Uwe,Kirschning, Andreas

, p. 461 - 466 (2007/10/03)

A convenient one-step transformation of primary and secondary amines into the corresponding unprotected guanidines using 4-benzyl-3,5-dimethyl-1H- pyrazole-1-carboxamidine and its polymer-bound variant is described. The scopes and limitations of the method, the microwave-assistance of amidination as well as a recycling protocol are examined. Georg Thieme Verlag Stuttgart.

Preparation of N-formamidinylamino acids from amino and formamidinesulfinic acids

Jursic,Neumann,McPherson

, p. 1656 - 1658 (2007/10/03)

A practical synthetic procedure for the conversion of amino acids into N-formamidinylamino acids using formamidinesulfinic acid in basic water solution is presented.

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