4-Guanidinobutyric acid

Base Information

• Chemical Name: 4-Guanidinobutyric acid
• CAS No.: 463-00-3
• Molecular Formula: C5H11 N3 O2
• Molecular Weight: 145.161
• Hs Code.: 2925290090
• European Community (EC) Number: 207-331-1
• NSC Number: 521717
• UNII: 15ADP48O8Q
• DSSTox Substance ID: DTXSID50196785
• Nikkaji Number: J196.182I
• Wikidata: Q27457468
• Metabolomics Workbench ID: 38341
• ChEMBL ID: CHEMBL21157
• Mol file: 463-00-3.mol

Synonyms:4-guanidinobutyric acid;gamma-guanidinobutyrate;gamma-guanidinobutyrate, monosodium salt;gamma-guanidinobutyric acid

Chemical Property of 4-Guanidinobutyric acid

Chemical Property:

• Vapor Pressure: 3.86E-05mmHg at 25°C
• Melting Point: 280-282 °C (dec.)
• Boiling Point: 377°Cat760mmHg
• PKA: 4.60±0.10(Predicted)
• Flash Point: 181.8°C
• PSA: 99.20000
• Density: 1.37g/cm³
• LogP: 0.52520
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Base (Slightly), Water (Slightly)
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 145.085126602
• Heavy Atom Count: 10
• Complexity: 140

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Guanidinobutanoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CC(=O)O)CN=C(N)N
• Uses: Gamma-Guanidinobutyric acid (4-GBA) is used to study intestinal transport by the human proton-coupled amino acid transporter(s) (hPAT1). 4-GBA is used with other model compounds such as 1,6-diaminohexane, 1,6-diguanidinohexane, and 1,6-di(cyanoguanidino)hexane to study the biodegradability of the biocide polyhexamethylene biguanide (PHMB).

Technology Process of 4-Guanidinobutyric acid

There total 22 articles about 4-Guanidinobutyric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

aminoiminomethanesulfonic acid (1184-90-3) + 4-amino-n-butyric acid (56-12-2) → 4-guanidinobutyric acid (463-00-3)

Guidance literature:

With potassium carbonate; In water; for 24h; Ambient temperature;

DOI:10.1055/s-1986-31777

Reference yield:

γ-guanidino butyraldehyde (14049-14-0) → 4-guanidinobutyric acid (463-00-3)

Guidance literature:

With Pisum sativum aminoaldehyde dehydrogenase 2; nicotinamide adenine dinucleotide; at 20 ℃; pH=9; aq. buffer; Enzymatic reaction;

DOI:10.1016/j.jmb.2009.12.015

Reference yield:

L-arginine (74-79-3,25212-18-4) → 4-guanidinobutyric acid (463-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1: arginine mono-oxygenase-2699 / aq. phosphate buffer / 2 h / 25 °C / pH 7.4

2: amidohydrolase-6564 / 1 h / 25 °C

With amidohydrolase-6564; arginine mono-oxygenase-2699; In aq. phosphate buffer;

DOI:10.1002/anie.201308136

upstream raw materials:

L-arginine

carbamimidothioic acid methyl ester

4-amino-n-butyric acid

CYANAMID

Downstream raw materials:

guanidino butyric acid amide

urea

4-amino-n-butyric acid

N^G-carbobenzoxy-4-guanidinobutanal

Refernces

• 1、 Hedges, Jason B.,Kuatsjah, Eugene,Du, Yi-Ling,Eltis, Lindsay D.,Ryan, Katherine S.. "Snapshots of the Catalytic Cycle of an O2, Pyridoxal Phosphate-Dependent Hydroxylase". . p. 965 - 974. Retrieved 2018.
• 2、 Hong, Hui,Fill, Taicia,Leadlay, Peter F.. "A common origin for guanidinobutanoate starter units in antifungal natural products". . p. 13096 - 13099. Retrieved 2014/01/06.
• 3、 Tylichova, Martina,Kopecny, David,Morera, Solange,Briozzo, Pierre,Lenobel, Rene,Snegaroff, Jacques,Sebela, Marek. "Structural and functional characterization of plant aminoaldehyde dehydrogenase from pisum sativum with a broad specificity for natural and synthetic aminoaldehydes". experimental part. p. 870 - 882. Retrieved 2011/04/24.