N-Acetyl-L-tyrosine
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N-Acetyl-L-tyrosine
structure -
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CAS No:
537-55-3
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Formula:
C11H13NO4
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Chemical Name:
N-Acetyl-L-tyrosine
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Synonyms:
L-Tyrosine,N-acetyl-;Tyrosine,N-acetyl-,L-;N-Acetyl-L-tyrosine;N-Acetyltyrosine;L-N-Acetyltyrosine;(2S)-2-Acetylamino-3-(4-hydroxyphenyl)propanoic acid;NSC 10853;(+)-(2S)-2-(Acetylamino)-3-(4-hydroxyphenyl)propanoic acid;Tyr-Excel;(2S)-2-Acetamido-3-(4-hydroxyphenyl)propanoic acid;29593-19-9
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CAS No:
Description
N-Acetyl-L-tyrosine originates from tyrosine through an AA acetylase, is associated with aromatic L-amino acid decarboxylase deficiency and tyrosinemia I.
Solid
N-acetyl-L-tyrosine is an N-acetyltyrosine in which the chiral centre has L configuration. It has a role as an EC 2.1.1.4 (acetylserotonin O-methyltransferase) inhibitor, a biomarker and a human urinary metabolite. It is a N-acyl-L-tyrosine and a N-acetyltyrosine. It is a conjugate acid of a N-acetyl-L-tyrosinate.|N-acetyltyrosine, also referred to as N-acetyl-L-tyrosine, is used in place of as a tyrosine precursor. [DB00135] is a non-essential amino acid with a polar side group. N-acetyltyrosine is administered as parenteral nutrition or intravenous infusion due to its enhanced solubility compared to tyrosine. It is typically administered as a source of nutritional support where oral nutrition is inadequate or cannot be tolerated.
Characteristics
86.63000
-0.2
Solid
1.304 g/cm3
151-153 °C
531.3ºC at 760 mmHg
275.1ºC
1.577
Soluble in water (25 mg/ml), and ethanol.
2-8ºC
154.5 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|149.44 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]
Safety Information
NONH for all modes of transport
3
R41
S26-S39
Xi
Stable. Incompatible with strong oxidizing agents.
P280-P305 + P351 + P338 + P310
H318
|Danger|H318 (99.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation]|P280, P305+P351+P338, and P310|Aggregated GHS information provided by 390 companies from 4 notifications to the ECHA C&L Inventory.
Drug Information
N-acetyltyrosine is indicated, in combination with several other amino acids and dextrose, as a peripherally administered source of nitrogen for nutritional support in patients with adequate stores of body fat in whom, for short periods, oral administration cannot be tolerated, is undesirable, or inadequate. It is also indicated, with other amino acids, 5-10% dextrose, and fat emulsion, for parenteral nutrition to preserve protein and reduce catabolism in stress conditions where oral administration is inadequate. When administered with other amino acids and concentrated dextrose, it is indicated for central vein infusion to prevent or reverse negative nitrogen balance in patients where the alimentary tract by the oral, gastrostomy, or jejestomy routes cannot or should not be used or in patients in which gastrointestinal absorption of protein is impaired, metabolic requirements for protein are substantially increased, or morbidity and mortality may be reduced by replacing amino acids lost from tissue breakdown|FDA Label
N-acetyltyrosine is used as a high solubility precursor to [DB00135] used due to [DB00135]'s poor solubility. It is deacetylated to form [DB00135].
N-acetyltyrosine is eliminated in the urine. The extent of urinary elimination versus utilization in the tissues appears to be related to the rapidity of infusion. When infused slowly in standard doses as in the clinical setting, about 35% is excreted unchanged in the urine. When larger doses are infused rapidly, much higher amounts are excreted reaching values up to 56%. In rat studies it was found that of the drug eliminated in the urine about 74% is present as unchanged N-acetyltyrosine and 23% is present as tyrosine.
Used as a source of [DB00135]. See [DB00135] for more information on its role and pharmacology.
acetyl-L-tyrosine
N-Acetyl-L-tyrosine Use and Manufacturing
20 mL of a solution of N-acetyl-l-tyrosine (25 mM) in200 mM borate buffer (pH 9.4) was warmed to 37 C. Aftercomplete dissolution of the N-acetylated amino acid, theround-bottomed flask was nitrogen purged and 24 muL of a2.5 mM solution of HRP (final concentration of 3 muM) wasadded. 50 muL of 30% H2O2was then rapidly added (finalconcentration of 24.5 mM) under dinitrogen, and the resultingreaction mixture was stirred for 1 h, protected from light.The pale-red solution obtained was immediately frozen andsubsequently lyophilized. The resulting solid was dissolvedin 1.5 mL of methanol and purified by thin-layer chromatography(silica gel matrix 60/F254von glass support with afluorescent indicator; 20 × 20 cm2, medium pore size of 60A; Sigma-Aldrich), using a solvent mixture of methanol/chloroform/water at 65:30:5 as the eluent. The bands wereobserved under a UV lamp and subsequently scraped off.The compound was recovered by suspending the silica in20 mL of methanol. After stirring for 15 min, filtration andevaporation under reduced pressure, NAc-diY was obtainedwith a yield of 23% and a chromatographic purity of 97%.White solid Rf (MeOH/CHCl3/H2O 65:30:5) = 0.33.HPLC-MS: tR = 8.65 min; m/z = 445.1 [C22H24N2O8 + H]+(Figure S1). 1H NMR (D2O, 400 MHz): delta = 1.79 (s, 6H, Me-Ac); 2.71-3.05 (m, 4H, Hbeta);4.28 (dd, 2H, J = 4.8 Hz, J = 8.6 Hz, Halpha);6.81 (d, 2H, J = 8.3 Hz, H5);6.94 (d, 2H, J = 2.0 Hz, H2);7.05 (dd, 2H, J = 2.0 Hz, J = 8.3 Hz, H6)ppm. See Fig. 1 for the atom labeling.
N-Acetyl-L-tyrosine is an analogue of L-tyrosine which stimulate the transport of L-Tyr, mainly by the ASC system.
L-Tyrosine, N-acetyl-: ACTIVE
Cosmetics -> Tanning
Computed Properties
Molecular Weight:223.22
XLogP3:-0.2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:223.08445790
Monoisotopic Mass:223.08445790
Topological Polar Surface Area:86.6
Heavy Atom Count:16
Complexity:259
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
To meet the nutritional needs of children, increase the amount of tyrosine to adapt to the metabolic characteristics of infants and young children.
Registered Holders
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AMINO GmbH
Active
Germany
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Jinyao Pharmaceutical Co., Ltd.
Active
China
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Yantai Luyin Pharmaceutical Co., Ltd.
Active
China
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