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W381918

Sigma-Aldrich

L-Arginine

99%, FCC, FG

Synonym(s):

(S)-2-Amino-5-guanidinopentanoic acid

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About This Item

Linear Formula:
H2NC(=NH)NH(CH2)3CH(NH2)CO2H
CAS Number:
74-79-3
Molecular Weight:
174.20
FEMA Number:
3819
Beilstein:
1725413
EC Number:
200-811-1
MDL number:
MFCD00002635
UNSPSC Code:
12164502
eCl@ss:
32160406
PubChem Substance ID:
24901894
Flavis number:
17.003
NACRES:
NA.21

biological source

synthetic

grade

FG

Agency

meets purity specifications of JECFA

reg. compliance

EU Regulation 1334/2008 & 872/2012
FCC
FDA 21 CFR 172.320

Assay

99%

form

powder or crystals

optical activity

[α]20/D +27°, c = 8 in 6 M HCl

mp

222 °C (dec.) (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

Organoleptic

faint

SMILES string

N[C@@H](CCCNC(N)=N)C(O)=O

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-/m0/s1

InChI key

ODKSFYDXXFIFQN-BYPYZUCNSA-N

Gene Information

human ... NOS1(4842) , NOS2(4843)
rat ... Ppm1a(24666)

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General description

L-Arginine is an amino acid that plays a key role in many physiological processes such as tissue repair and reproduction. It is a key precursor for synthesizing nitric oxide in mammals. Due to these factors, the dietary supplementation with L-arginine may show a range of health benefits.

Application


  • Metabolomic approaches to dissect dysregulated metabolism in the progression of pre-diabetes to T2DM.: This study employs L-Arginine to examine metabolic changes during the transition from pre-diabetes to type 2 diabetes mellitus, offering new targets for early intervention (Ji et al., 2024 Jun). Link to the article.

  • Amino acid profile alteration in age-related atrial fibrillation.: Investigates the role of L-Arginine in cardiovascular aging, highlighting its potential in developing therapeutic strategies against atrial fibrillation associated with aging (Huang et al., 2024 Mar). Link to the article.

Biochem/physiol Actions

Substrate of nitric oxide synthase, which is converted to citrulline and nitric oxide (NO). Induces insulin release by a nitric oxide-dependent mechanism.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

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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Blood pressure and metabolic changes during dietary L-arginine supplementation in humans.
Siani A, et al.
American Journal of Hypertension, 13(5), 547-551 (2000)
L-Arginine Research Progress (2012)
Krishnan Suresh Kumar et al.
European journal of medicinal chemistry, 45(11), 5474-5479 (2010-08-21)
A new series of 3-(benzylideneamino)-2-phenylquinazoline-4(3H)-ones were prepared through Schiff base formation of 3-amino-2-phenyl quinazoline-4(3)H-one with various substituted carbonyl compounds. Their chemical structures were elucidated by spectral studies. Cytotoxicity and antiviral activity were evaluated against herpes simplex virus-1 (KOS), herpes simplex
Diane N Singhroy et al.
Retrovirology, 10, 73-73 (2013-07-23)
Protein arginine methyltransferase 6 (PRMT6) is a nuclear enzyme that methylates arginine residues on histones and transcription factors. In addition, PRMT6 inhibits HIV-1 replication in cell culture by directly methylating and interfering with the functions of several HIV-1 proteins, i.e.
John Pernow et al.
Cardiovascular research, 98(3), 334-343 (2013-02-19)
Functional integrity of the vascular endothelium is of fundamental importance for normal vascular function. A key factor regulating endothelial function is the bioavailability of nitric oxide (NO). Recently, the enzyme arginase has emerged as an important regulator of NO production
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