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G6878

Sigma-Aldrich

3-Guanidinopropionic acid

≥97.5% (TLC)

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Synonym(s):
β-Guanidinopropionic acid
Linear Formula:
HN=C(NH2)NHCH2CH2COOH
CAS Number:
353-09-3
Molecular Weight:
131.13
Beilstein:
1705262
EC Number:
206-530-0
MDL number:
MFCD00045939
UNSPSC Code:
12352209
PubChem Substance ID:
24895277
NACRES:
NA.26

Assay

≥97.5% (TLC)

Quality Level

200

form

powder or crystals

color

white

mp

222 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

NC(=N)NCCC(O)=O

InChI

1S/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7)

InChI key

KMXXSJLYVJEBHI-UHFFFAOYSA-N

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Biochem/physiol Actions

β-Guanidinopropionic acid is studied for potential use during protein refolding as an anti-aggregatory molecule similar to L-arginine. β-Guanidinopropionic acid may be used to study its proliferative activity for endothelial cells contributing to wound healing. β-Guanidinopropionic acid is closely related to leptin.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A Bexfield et al.
The British journal of dermatology, 162(3), 554-562 (2009-10-06)
Maggot therapy, utilizing the larvae of Lucilia sericata, has been reported to reduce the bacterial load within wounds and also to enhance wound healing. Maggot excretions/secretions (ES) have been shown to have a role in the success of maggot therapy.
Inge Oudman et al.
PloS one, 8(1), e52879-e52879 (2013-01-18)
Creatine kinase plays a key role in cellular energy transport. The enzyme transfers high-energy phosphoryl groups from mitochondria to subcellular sites of ATP hydrolysis, where it buffers ADP concentration by catalyzing the reversible transfer of the high-energy phosphate moiety (P)
Shirin Mirshamsi et al.
Regulatory peptides, 141(1-3), 19-24 (2007-03-10)
A number of hormones, including leptin, have been shown to inhibit food intake in humans and animals. Analogues of 3-guanidinopropionic acid have also been found to reduce total food intake, but their mechanisms of action have not been well studied.
Yoshinobu Ohira et al.
Bioscience, biotechnology, and biochemistry, 75(6), 1085-1089 (2011-06-15)
The effects of supplementation with creatine (Cr) and its analog, β-guanidinopropionic acid (β-GPA), on the differentiation of myoblasts and the numbers of nucleoli were studied in C2C12 cells. The cells were cultured in differentiation medium for 4 d. Then Cr
Tamas L Horvath et al.
Neurobiology of disease, 43(1), 152-162 (2011-03-17)
Guanidinopropionic acid (GPA) increases AMPK activity, mitochondrial function and biogenesis in muscle and improves physiological function, for example during aging. Mitochondrial dysfunction is a major contributor to the pathogenesis of Parkinson's disease. Here we tested whether GPA prevents neurodegeneration of
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