58069-82-2

Basic information

• Product Name: UREA-13C
• Synonyms: UREA- 13C 99%;UREA (13C, 99%, 15N2, 98%);UREA-13C USP(CRM STANDARD);UREA (13C, 99%);Urea-13C - Research Grade;Urea-13C ,99 atom % 13C [99 atom % 13C];Urea C 13 (150 mg);Aquacare-13C
• CAS NO: 58069-82-2
• Molecular Formula: CH₄N₂O
• Molecular Weight: 61.06
• Product Categories: Carbon-13 Salts;cGMPStable Isotopes;Alphabetical Listings;Stable Isotopes;U-Z;Aliphatics;Amines;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals
• Mol File: 58069-82-2.mol

Chemical Properties

• Melting Point: 132-135 °C(lit.)
• Appearance: /
• Density: 1.212 g/cm³
• Refractive Index: 1.468
• Storage Temp.: 15-25°C
• Solubility: DMSO (Soluble), Methanol (Slightly)
• CAS DataBase Reference: UREA-13C(CAS DataBase Reference)
• NIST Chemistry Reference: UREA-13C(58069-82-2)
• EPA Substance Registry System: UREA-13C(58069-82-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 58069-82-2(Hazardous Substances Data)

Usage

Uses

Used in Medical Applications:
UREA-13C is used as a diagnostic tool for [application reason] in the medical industry. It helps in the detection and monitoring of various health conditions related to nitrogen metabolism and excretion.
Used in Pharmaceutical Applications:
UREA-13C is used as an excipient or active ingredient in the pharmaceutical industry for [application reason]. It can be incorporated into medications designed to regulate nitrogen excretion or treat conditions related to protein metabolism.
Used in Cosmetic Applications:
UREA-13C is used as an emollient in the cosmetic industry for [application reason]. Its skin-beneficial properties make it a valuable component in skincare products, promoting hydration and maintaining skin health.
Used in Agricultural Applications:
UREA-13C is used as a diuretic in the agricultural industry for [application reason]. It can be utilized in veterinary medicine to help regulate nitrogen excretion in livestock, ensuring their overall health and well-being.
Used in Research Applications:
UREA-13C is used as a research compound in the scientific industry for [application reason]. Its stable isotope labeling allows for the tracking of metabolic pathways and the study of protein catabolism in various biological systems.

InChI:InChI=1/CH4N2O/c2-1(3)4/h(H4,2,3,4)/i1+1

Synthetic route

potassium <13C>cyanate → 13C urea (58069-82-2)

Conditions	Yield
With ammonium sulfate; ammonium hydroxide at 70℃; for 4h;	87%

trichloro[13C]methyl phenyl sulfide (1071435-30-7) → 13C urea (58069-82-2) + (13C)-guanidine hydrochloride (286013-04-5)

Conditions	Yield
Stage #1: trichloro[13C]methyl phenyl sulfide With ammonia In ethanol; dichloromethane; water at -80 - 20℃; for 72.5h; Stage #2: With hydrogenchloride; water	A 49% B 47%

<13CO>-N-methyl-N-nitrosourea (MNU) → diazomethane (186581-53-3, 908094-01-9) + 13C urea (58069-82-2) + carbonic acid monomethyl ester (7456-87-3) + [13C]cyanic acid (118832-13-6) + carbonate ion + (13)CH2NO5P(2-)

Conditions	Yield
With sodium hydroxide; phosphate buffer In methanol; water at 22℃; Product distribution; other reagents, temperature;

ammonium sulfate + potassium <13C>cyanate → 13C urea (58069-82-2)

Conditions	Yield
recrystn. from ethanol;

phenylethane 1,2-diol (93-56-1) + 13C urea (58069-82-2) → 4-phenyl (2-13C)-1,3-dioxolan-2-one

Conditions	Yield
With iron(II) bromide In 1,4-dioxane at 150℃; for 18h; Inert atmosphere; Sealed tube;	90%

13C urea (58069-82-2) → 13C3-cyanuric acid (201996-37-4)

Conditions	Yield
In sulfolane at 205℃; under 100 Torr; for 2h;	88.4%
In sulfolane; cyclohexanol at 50 - 200℃;	87%
With sulfolane; cyclohexanol at 60 - 210℃; for 3h;

13C urea (58069-82-2) + [13C2,15N3]5,6-diaminopyrimidine-2,4(1H,3H)-dione hemisulfate → [13C3,15N3]uric acid

Conditions	Yield
at 190℃; for 2h;	80%

13C urea (58069-82-2) + Glyoxal (131543-46-9) → C2(13)C2H6O2N4

Conditions	Yield
With hydrogenchloride In water at 85 - 90℃;	78%

13C urea (58069-82-2) + methyl (2RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate (52263-88-4) → C16(13)CH16N2O2

Conditions	Yield
With nickel(II) acetylacetonate; potassium fluoride; phenylsilane; zinc; bis(2-diphenylphosphinoethyl)phenylphosphine In 1-methyl-pyrrolidin-2-one at 90 - 140℃; for 20h;	75%

13C urea (58069-82-2) + ethyl 2-cyanoacetate (105-56-6) → 6-amino[2-13C]uracil

Conditions	Yield
With sodium ethanolate In ethanol for 5h; Heating;	74%

13C urea (58069-82-2) + Propiolic acid (471-25-0) → [2-13C]-pyrimidine-2,4(1H,3H)-dione (35803-45-3)

Conditions	Yield
With PPA at 85℃; for 6h;	66%
Stage #1: 13C urea; Propiolic acid at 95 - 110℃; Stage #2: With water; sodium hydroxide	64%

13C urea (58069-82-2) + benzil (134-81-6) → [2-13C]phenytoin

Conditions	Yield
With potassium hydroxide at 100℃; for 3h;	65%

5,6-diaminouracil (3240-72-0) + 13C urea (58069-82-2) → <8-13C>uric acid (139290-36-1)

Conditions	Yield
at 170℃;	60%

13C urea (58069-82-2) + methyl p-toluene sulfonate (80-48-8) → O-methyl-[13C]isourea p-methylsulfonate salt (88597-10-8)

Conditions	Yield
Methylation; Heating;	60%
1.) 100 deg C, 5 h; 2.) acetone, RT, 1 h; Yield given. Multistep reaction;

13C urea (58069-82-2) + 2-bromo-3-methyl-butyryl bromide (26464-05-1) → C5(13)CH11BrN2O2

Conditions	Yield
In tetrahydrofuran for 15h; Heating;	48%

13C urea (58069-82-2) → 6-chlorouracil-(13)C2

13C urea (58069-82-2) + diethyl diethylmalonate (77-25-8) → [2-13C]barbital

Conditions	Yield
With sodium ethanolate 1.) EtOH, RT, 10 min, 2.) EtOH, reflux, 12 h; Yield given. Multistep reaction;

13C urea (58069-82-2) + ethyl 2-hydroxy-2,2-dimethylethanoate (80-55-7) → [2-13C]dimethadione

Conditions	Yield
With sodium ethanolate 1.) ETOH, 0 deg C, 2.) EtOH, reflux, 30 h; Yield given. Multistep reaction;

13C urea (58069-82-2) + [13C](methoxy) chloroformic acid methyl ester → [13C]2(urea,methoxy) methoxycarbonyl urea

Conditions	Yield
at 100℃; for 1h;

13C urea (58069-82-2) + DL-5-chlorohydantoin (32282-43-2) → DL-2-(13)C-allantoin + DL-[H2N(13)CO]allantoin

Conditions	Yield
In nitromethane for 1h; Reflux;

13C urea (58069-82-2) + [13C,15N]5,6-diaminopyrimidine-2,4(1H,3H)-dione → [13C2,15N2]uric acid

Conditions	Yield
at 185℃; for 1h;	296 mg

13C urea (58069-82-2) → carbon dioxide (1111-72-4)

Conditions	Yield
With carbon dioxide; urease In water for 1h; Catalytic behavior; Solvent; Concentration; Sealed tube; Enzymatic reaction;

Upstream product

• 1071435-30-7 trichloro[13C]methyl phenyl sulfide 

Downstream Products

• 35803-45-3 [2-13C]-uracil 
• 1111-72-4 carbon dioxide 
• 201996-37-4 [¹³C]cyanuric acid 

Relevant articles and documents

THE MEASUREMENT OF SYNTHESIS RATES OF ALBUMIN AND FIBRINOGEN IN RABBITS.

1. A formula is proposed for calculating fractional synthesis rates of

SINGLE CARBON PRECURSOR SYNTHONS

The chemistry of [13C]methyl phenyl sulfide is exploited to produce new isotopically labeled precursors that allow for the facile assembly of a wide range of labeled molecules from simple and relatively inexpensive starting materials. These compounds are applicable to a variety of research areas such as quantum computing, metabolism and materials science.

The mechanism of decomposition of N-methyl-N-nitrosourea (MNU) in water and a study of its reactions with 2'-deoxyguanosine, 2'-deoxyguanosine 5'-monophosphate and d(GTGCAC)

The carcinogenicity of N-methyl-N-nitrosourea (MNU) arises, from its ability to methylate DNA, This occurs in an aqueous environment and therefore an appreciation of the mode of decomposition of MNU in water is essential to understanding the mechanism of DNA methylation and its base sequence dependence. The kinetics of MNU hydrolyses are shown to be first order in MNU with a steep rise in rate above pH 8. Using NMR for in situ monitoring of reaction intermediates and products from hydrolyses of [13CO]MNU, [15NH2]MNU and [13CH3]MNU, it is proved that base-induced hydrolysis of MNU is initiated by deprotonation at the carbamoyl group. The critical reactive species are shown to be the methyldiazonium ion (Me-N2+) and cyanate (NCO-). Investigations of reactions of [13CH3]MNU with 2'-deoxyguanosine (dGuo) and 2-deoxyguanosine 5'-monophosphate (dGuo-5P) showed that: a) the site of methylation of dGuo is highly pH-dependent (relatively more N-1 and O6-methylation compared to N-7 occurs at higher pH; b) the principal site of methylation of dGuo-5P by MNU is at phosphate; c) incorporation of deuterium into methyl groups occurs in D2O at higher pH. Methylation of the oligonucleotide d(GT[15N]GCAC) by MNU in D2O showed partial deuteriation of the N7-methyl groups of the guanines, whilst methylation by MNU in water indicated no significant preference for either guanine with respect to N7-methylation.

Concomitant oxygen-18 enrichment in commercial carbon-13 labelled urea

By mass spectroscopy, 50-fold oxygen-18 enrichment over natural abundance was observed in commercial 13C-urea (99 atom % 13C) synthesized from 13C-carbon monoxide that had been 13C-enriched by cryogenic distillation. in contrast, 13C-urea synthesized from 13C-potassium cyanide (a 13C-labened compound having no oxygen atom) showed the natural abundance level of oxygen-18 .