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CAS No. : | 352-97-6 | MDL No. : | MFCD00004278 |
Formula : | C3H7N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BPMFZUMJYQTVII-UHFFFAOYSA-N |
M.W : | 117.11 | Pubchem ID : | 763 |
Synonyms : |
Guanidinoacetic acid;GAA;AI3-17119;NSC 26360;NSC 227847;NSC 1901;Guanidinoacetate
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 4.0 |
Molar Refractivity : | 27.41 |
TPSA : | 99.2 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.97 cm/s |
Log Po/w (iLOGP) : | -0.59 |
Log Po/w (XLOGP3) : | -1.35 |
Log Po/w (WLOGP) : | -1.45 |
Log Po/w (MLOGP) : | -3.63 |
Log Po/w (SILICOS-IT) : | -1.58 |
Consensus Log Po/w : | -1.72 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 0.48 |
Solubility : | 356.0 mg/ml ; 3.04 mol/l |
Class : | Highly soluble |
Log S (Ali) : | -0.23 |
Solubility : | 68.4 mg/ml ; 0.584 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.61 |
Solubility : | 475.0 mg/ml ; 4.06 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.81 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P302+P352-P304+P340-P305+P351+P338-P332+P313-P337+P313-P501 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With hydrogenchloride; In water; at 120℃; for 22h;Heating; | The synthesis of polyandrocarpamines A & B (PAC1 and PAC2) was performed from corresponding benzaldehyde derivatives, n-propylamine and 2-aminoimidazolin-4-one, the preparation of which was previously described in literature [53] (Figure 5). Guanidine (2.95 mmol, 1eq) and HClaq 6N (9 mL) were heated at 120 C for 22 h. Water was removed under vacuum and the crude product was solubilized in hot ethanol (9 mL). Diethylether (6 mL) was added, then the mixture was cooled to 0 C. After 6 h, filtration was performed and the 2-aminoimidazolin-4-one was isolated as a white powder with a 49% yield. RMN 1H (D2O): delta 4.18 (s, 2H, H-1); RMN 13C (D2O):delta 48.5 (C-1); 174.9 (C=O); [M - HCl]+ = 99.0427 (99.0433 C3H5N3O); F = 200-202 C. PAC1 and PAC2 were then produced by mixing the corresponding benzaldehyde (vanillin or catechaldehyde 1.48mmol, 1 eq) with n-propylamine (2.95 mmol, 2 eq). The imine formation was performed under microwave irradiation at 60 C for 30 min (maximized authorized power 60 W). Acetonitrile was added to the crude imine with 2-aminoimidazolin-4-one (1.48 mmol, 1 eq), and the mixture was stirred at reflux for 63 h. The solvent was removed under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.6% | With ammonia; In water; at 60℃; for 4h;pH 11.0; | To a 250 mL four-necked flask equipped with a reflux condenser, a dropping funnel, and a thermometer, 27.0 g (0.36 mol) of glycine and 40.5 g of water were added, stirred and dissolved, and adjusted to pH 11 by addition of liquid ammonia. The temperature was increased to 60 C, (0.327 mol) of 50% aqueous solution of cyanamide, stirred for 4 h, filtered and washed with the filtrate. In a separate kettle, crude guanidine acetate and 4 times the mass of DMF were added,Heated to 40 C stirring 0.5h and then cooled to 0 C, by suction filtration, DMF washing filter cake,Finally, 39.93 g of guanidinoacetic acid was obtained with a yield of 94.6% and a content of 99.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Among the compounds of formula (III), mention may be made especially of the following particularly preferred compounds: ... creatine monohydrate creatinine hydrochloride agmatine agmatine sulfate guanidinoacetic acid guanidinosuccinic acid 3-guanidinopropionic acid beta-N-methylguanidinopropionic acid ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.45% | Example 18; [6-Cyano-6-(4-methoxydibenzo[ft,rf]furan-l-yl)-5,6,7,8-tetrahydroquinazolin-2-yl] amino} acetic acid; A mixture of the compound obtained in example 6 (lOOmg, 0.267mmol), guanidine acetic acid and sodium hydroxide (54mg, l mol) in 10 ml of methanol was stirred at 60-700C for 8 hrs. Methanol was evaporated under <n="45"/>vacuum and the reaction mass was diluted with 10 ml of water. The aqueous layer was washed with ether, acidified with 0.1 N HCl to pH 2 and extracted with ethyl acetate. The organic layer was washed with water followed by brine, and concentrated under vacuum. The crude product was crystallized form hexane to give 60mg (52.45% yields) of a yellow colored solid.1H-NMR (300MHz, DMSO-d6); 8.24 (d, J=6.4, IH); 8.2 (s, IH); 7.85 (d, J=8.1, IH); 7.63 (t, J=7.6, IH); 7.53 (t, J=7.4, IH); 7.38 (d, J=8.5, IH); 7.25 (d, J=8.5, IH); 6.67 (s, IH); 4.1 (s, 3H); 3.7 (s, 2H); 3.7-3.5 (m, 2H); 3- 3.2 (m, 2H); 2.9-2.8 (m, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 1 Guanidinoacetyl-L-histidine.H2 O (n=1) was prepared from glycyl-L-histidine and S-ethylisothiourea.H2 SO4. Solutions of 1.50 g. of S-ethylisothiourea.H2 SO4 in 5 ml of H2 O and 1.74 g. of Gly-His.HCl in 3 ml of H2 O were adjusted to pH 8-9 with 4 N NaOH. They were then mixed and kept at room temperature for a week. The cloudy suspension was filtered and the filtrate concentrated to dryness in vacuo. The residue, after addition of a small amount of EtOH, was dried in vacuo. A small amount of H2 O was added to dissolve the dry residue and resulting solution was poured onto the column (2.5 cm i.d. * 30 cm Amberlite CG-120, 200-400 mesh, pyridine form). H2 O, 1.0 M pyridine, 2.0 M pyridine, and 1.0 M pyridine--0.5 M NH4 OH were used as the effluent solutions. Each fraction was tested for ninhydrin, Pauli, and Sakaguchi reactions. The fractions containing guanidinoacetyl-L-histidine were pooled and concentrated to dryness in vacuo. Cryst from H2 O--EtOH; yield, 69.2%; mp, 108-111 C., decomp. Hydrolysis (6 N HCl, 110, 24 hours.) gave guanidinoacetic acid and histidine, as confirmed be tlc. (thin layer chromatography). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With sodium carbonate; In water; glycine; | Example 2 In a 100 ml flask were added 5 g of glycine, 9,83 mg of 1-amidino-1,2,4-triazol-hydrochloride and 7.06 g of sodium carbonate, dissolved in 166 ml of water. The reaction suspension was stirred at rt over night. The precipitate was filtered, washed with methanol and dried at rt under vacuum to give 8.08 g of amidinoglycine (79% yield), m.p. 279-283C (dec.). |
[ 57-00-1 ]
2-(1-Methylguanidino)acetic acid
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