| Identification | More | [Name]
D(-)-Arginine | [CAS]
157-06-2 | [Synonyms]
ARGININE, D-
D-2-AMINO-5-GUANIDINOVALERIC ACID
D-ARG
D-(-)-ARGININE
D-ARGININE
H-D-ARG-OH
(R)-2-AMINO-5-GUANIDINOPENTANOIC ACID
RARECHEM AB PP 1748
R-(-)-ARGININE
H-D-Arginine
(-)-D-arginine hydrate
D-ARGININE FREE BASE
d-2-amino-5-guanidinopentanoic acid
(2R)-2-amino-5-(diaminomethylideneamino)pentanoic acid
ARGININE, D-(RG)
D-ARG.FREE BASE
D-ARGININE BASE
(2R)-2-Amino-5-(diaminomethylideneamino)pentanoic acid hydrate
D-Arginine ,99% | [EINECS(EC#)]
205-866-5 | [Molecular Formula]
C6H14N4O2 | [MDL Number]
MFCD00063116 | [Molecular Weight]
174.2 | [MOL File]
157-06-2.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
226 °C (dec.) (lit.) | [alpha ]
-28.5 º (c=8, 6 N HCl) | [Boiling point ]
305.18°C (rough estimate) | [density ]
1.2297 (rough estimate) | [refractive index ]
-23 ° (C=8, 6mol/L HCl) | [storage temp. ]
Store at 0-5 | [solubility ]
Aqueous Acid (Slightly), Water (Slightly) | [form ]
Solid | [pka]
2.49±0.24(Predicted) | [color ]
White to Off-White | [Water Solubility ]
SOLUBLE | [Sensitive ]
Air Sensitive | [Detection Methods]
HPLC,NMR | [BRN ]
1725412 | [Major Application]
peptide synthesis | [InChI]
1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m1/s1 | [InChIKey]
ODKSFYDXXFIFQN-SCSAIBSYSA-N | [SMILES]
N[C@H](CCCNC(N)=N)C(O)=O | [LogP]
-0.999 (est) | [CAS DataBase Reference]
157-06-2(CAS DataBase Reference) | [EPA Substance Registry System]
157-06-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36:Irritating to the eyes.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
CF1934220 | [F ]
9 | [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29252900 | [Storage Class]
11 - Combustible Solids |
| Questions and Answers (Q&A) | Back Directory | [Description]
D-arginine is the D-form of arginine, which is a kind of amino acids. It can be reacted with hydrogen peroxide for non-enzymatic synthesis of nitric oxide. It has certain pharmacological activities. For example, its derivative, 1-deamino-8-D-arginine vasopressin is useful for the management of haemophilia and von Willebrand’s disease. It also has the potential to inhibit the proliferation of certain cancer cells. In biological research, D-arginine is frequently used in the studies of L-arginine/nitric oxide pathway as an inactive form of L-arginine.
| [References]
https://www.alfa.com/zh-cn/catalog/A16137/
Iannucci, N. B., et al. "Antiproliferative effect of 1-deamino-8-D-arginine vasopressin analogs on human breast cancer cells." Future Medicinal Chemistry 3.16(2011):1987-1993.
Ripoll, Giselle, et al. "Angiostatic activity of 1-Deamino-8-D-Arginine vasopressin and novel peptide analogues in breast cancer cells." Cancer Research 68(2008).
Navarro, Eduardo, et al. "Toxicological and Pharmacological Effects of D-Arginine." Basic & Clinical Pharmacology & Toxicology97.3(2005):149-154.
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| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Uses]
Arginine is an essential amino acid found in food and plant sources, and many biological systems.
D-Arginine is extensively used in studies on L-arginine/nitric oxide pathway as an inactive form of L-arginine, even in man.
D-Arginine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). D-Arginine can be found in human epidermis and platelet tissues. Within the cell, D-arginine is primarily located in the peroxisome. D-Arginine specifically can inhibit arginine decarboxylase enzymes and also functions as a metabolite. | [Definition]
ChEBI: A D-alpha-amino acid that is the D-isomer of arginine. | [in vivo]
D-arginine (1 mg/kg, i.v., caudal veins, every two days) sensitize osteosarcoma to radiotherapy in a mouse model of subcutaneous osteosarcoma[3].
The number of D-arginine residues in cell-penetrating peptides (i.v.) significantly affects their cellular uptake behavior and systemic toxicity in mice[4].
D-Arginine (700 mg/kg, i.p.) displays central stimulant properties and increases spontaneous motor activity in mice[5].
D-arginine (i.p.) shows a light toxicity order (LD50: 2800 mg/kg) in mice[5].
D-arginine (1400 mg/kg, i.p.) protects against Pentylenetetrazole-induced convulsions in mice[5].
D-arginine (1000 mg/kg, p.o., 16 weeks) significantly alters various enzymes and metabolites in the arginine metabolic pathways in male SD rats[6].
D-arginine (1000 mg/kg, s.c., coadministered with L-arginine) blocks antinociception elicited by L-arginine (HY-N0455) in mice with Carrageenin-induced hyperalgesia[7].
D-arginine (20 mg/kg, s.c.) does not significantly alter the percentage of antinociception in mice[8].
| Animal Model: | Female BALB/c mice (anesthetized by intraperitoneal injection of 3% pentobarbital sodium; K7M2 cells were injected subcutaneously; X-ray irradiation)[2] | | Dosage: | 1 mg/kg | | Administration: | Intravenous injection (i.v.), caudal veins, every two days | | Result: | Inhibited tumor volume (20 days).
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| [IC 50]
Human Endogenous Metabolite |
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