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D(-)-Arginine

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CAS:157-06-2
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  • 2026-02-11
  • CAS:157-06-2
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D(-)-Arginine Basic information
Product Name:D(-)-Arginine
Synonyms:(2R)-2-ammonio-5-(diaminomethylideneammonio)pentanoate;R-(-)-ARGININE;(R)-2-AMINO-5-GUANIDINOPENTANOIC ACID;RARECHEM AB PP 1748;D-ARG;D-(-)-ARGININE;D-ARGININE;D-2-AMINO-5-GUANIDINOVALERIC ACID
CAS:157-06-2
MF:C6H14N4O2
MW:174.2
EINECS:205-866-5
Product Categories:amino;Amino Acids;Arginine [Arg, R];Amino Acids and Derivatives;alpha-Amino Acids;Amino Acids;Biochemistry;for Resolution of Acids;Optical Resolution;Synthetic Organic Chemistry;PROTECTED AMINO ACID & PEPTIDES;Amino Acids Derivatives;chiral
Mol File:157-06-2.mol
D(-)-Arginine Structure
D(-)-Arginine Chemical Properties
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. Keep in dark place,Inert atmosphere,Room temperature
solubility Aqueous Acid (Slightly), Water (Slightly)
pka2.49±0.24(Predicted)
form Solid
color White to Off-White
Water Solubility SOLUBLE
Sensitive Air Sensitive
BRN 1725412
Major Applicationpeptide synthesis
InChI1S/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
InChIKeyODKSFYDXXFIFQN-SCSAIBSYSA-N
SMILESN[C@H](CCCNC(N)=N)C(O)=O
LogP-0.999 (est)
CAS DataBase Reference157-06-2(CAS DataBase Reference)
EPA Substance Registry SystemD-Arginine (157-06-2)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36-36/37/38-20/21/22
Safety Statements 26-36
WGK Germany 3
RTECS CF1934220
9
TSCA TSCA listed
HazardClass IRRITANT
HS Code 29252000
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
D(-)-Arginine English
ACROS English
SigmaAldrich English
ALFA English
D(-)-Arginine Usage And Synthesis
DescriptionD-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.
Chemical Propertieswhite to light yellow crystal powde
UsesArginine 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.
Uses1-Deamino-8-D-arginine vasopressin makes a new pharmacological approach to the management of haemophilia and von Willebrand's disease. A novel nonenzymatic pathway for the generation of nitric oxide is by the reaction of hydrogen peroxide and d- or l-arginine.
DefinitionChEBI: D-arginine is a D-alpha-amino acid that is the D-isomer of arginine. It has a role as an EC 4.1.1.19 (arginine decarboxylase) inhibitor and a mouse metabolite. It is a D-alpha-amino acid and an arginine. It is a conjugate base of a D-argininium(1+). It is a conjugate acid of a D-argininate. It is an enantiomer of a L-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).
IC 50Human Endogenous Metabolite
Referenceshttps://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.
D(-)-Arginine Preparation Products And Raw materials
Raw materialsD-Ornithine monohydrochloride
Tag:D(-)-Arginine(157-06-2) Related Product Information
L(+)-Arginine EPA Guanidineacetic acid 3-Guanidinopropionic acid ARGINASE 6-Aminocaproic acid ALTRENOGEST 5-Amino-2-methylpyridine D-Lysine H-D-CIT-OH D-Ornithine monohydrochloride D-Ribose Glycine Arginine arginine aspirin BOC-D-Arg(Tos)-OH D-(-)-Arginine hydrochloride N-Fmoc-N'-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-D-arginine

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