Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); oxygen; cobalt(II) acetate; acetic acid at 80℃; for 15h; | 92% |
With potassium hydroxide; potassium hexacyanoferrate(III) |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 115 - 120℃; for 2h; Temperature; Large scale; | 91.9% |
(2Z)-(2,5-dioxoimidazolidin-4-ylidene)acetic acid
orotic acid
Conditions | Yield |
---|---|
With potassium hydroxide at 64℃; for 3h; | 85% |
With potassium hydroxide at 64℃; for 3h; Mechanism; Kinetics; var. conc. of KOH; | 85% |
orotic acid
Conditions | Yield |
---|---|
With oxygen; palladium dichloride In N,N-dimethyl-formamide at 80℃; under 760.051 Torr; for 36h; Reagent/catalyst; Solvent; Pressure; Temperature; | 85% |
Conditions | Yield |
---|---|
Stage #1: glycoluril; Glyoxal With sodium hydroxide In water for 8h; Autoclave; Reflux; Large scale; Stage #2: With chlorine at 20℃; Time; Large scale; | 33% |
orotoaldehyde
A
6-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione
B
orotic acid
Conditions | Yield |
---|---|
With potassium hydroxide |
orotoaldehyde
orotic acid
Conditions | Yield |
---|---|
With sodium dichromate; sulfuric acid |
6-oxo-2-thioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbaldehyde
orotic acid
Conditions | Yield |
---|---|
With sodium dichromate; sulfuric acid | |
Multi-step reaction with 2 steps 1: aqueous KOH 2: aqueous alkali .H2O2 View Scheme |
Conditions | Yield |
---|---|
With alkali .H2O2 |
Conditions | Yield |
---|---|
With potassium hydroxide; potassium hexacyanoferrate(III) 22 d; |
Conditions | Yield |
---|---|
With hydrogenchloride |
6-diethoxymethyl-1H-pyrimidine-2,4-dione
orotic acid
Conditions | Yield |
---|---|
With sodium dichromate; sulfuric acid | |
Multi-step reaction with 2 steps 1: Hydrolysis 2: Na2Cr2O7/H2SO4 View Scheme |
6-diethoxymethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
orotic acid
Conditions | Yield |
---|---|
With sodium dichromate; sulfuric acid | |
Multi-step reaction with 3 steps 1: aqueous H2O2; aqueous NaOH 2: Hydrolysis 3: Na2Cr2O7/H2SO4 View Scheme | |
Multi-step reaction with 2 steps 1: aqueous H2O2; aqueous NaOH 2: Na2Cr2O7/H2SO4 View Scheme |
(2,5-dioxo-imidazolidin-4-yliden)-acetic acid
orotic acid
Conditions | Yield |
---|---|
With potassium hydroxide |
2,6-Dioxo-3,6-dihydro-2H-[1,3]oxazine-4-carboxylic acid
orotic acid
Conditions | Yield |
---|---|
With ammonia In various solvent(s) |
methyl N1,N3-dibenzyloxymethyl-orotate
orotic acid
Conditions | Yield |
---|---|
With trimethylsilyl iodide; water 1.) chloroform, reflux, 6 h, 2.) reflux, 30 min; 160-180 deg C, 15 min; reflux; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
at 37℃; for 72h; Product distribution; strain 556F from Bacillus subtilis, pH 7.2; effect of different amounts of uracil, other mutants of Bacillus subtilis; |
Conditions | Yield |
---|---|
With dihydroorotate dehydrogenase; bis(1-chloro-2-propyl) ether; All-Trans Coenzyme Q6; Triton X-100 In water at 37℃; pH=7.8; | |
With dihydroorotate dehydrogenase In phosphate buffer at 22℃; pH=7; Enzyme kinetics; Further Variations:; also in the presence of detergent; | |
With human dihydroorotate dehydrogenase; 2,3-dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-1,4-benzoquinone Enzyme kinetics; | |
With 2,3-Dimethoxy-5-methyl-1,4-benzoquinone; 2,6-Dichlorophenolindophenol; glycerol; sodium chloride; Triton X-100 In water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid Microbiological reaction; Enzymatic reaction; | |
With decylubiquinone; pfDHODH at 25℃; Enzyme kinetics; buffer C; |
orotic acid
(2,5-dioxo-imidazolidin-4-yliden)-acetic acid
orotic acid
orotic acid
Conditions | Yield |
---|---|
With potassium hydroxide |
orotic acid
Conditions | Yield |
---|---|
With potassium hydroxide |
A
orotic acid
Conditions | Yield |
---|---|
With sodium hydroxide |
ureidosuccinic acid
orotic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 77 percent / 20percent aq. HCl 2: 71 percent / Br2 / acetic acid / 4 h / 100 °C 3: 85 percent / aq. KOH / 3 h / 64 °C / var. conc. of KOH View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 71 percent / Br2 / acetic acid / 4 h / 100 °C 2: 85 percent / aq. KOH / 3 h / 64 °C / var. conc. of KOH View Scheme | |
Multi-step reaction with 2 steps 1: bromine; acetic acid / Beim Erhitzen des Reaktionsprodukts mit H2O 2: aqueous KOH View Scheme |
5-fluoro-1H-indole-2,3-dione
5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
orotic acid
Conditions | Yield |
---|---|
1.1 g (73%) |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; water | |
With sodium hydroxide for 2h; Reflux; Large scale; |
orotidine 5'-monophosphate
A
orotic acid
B
5-phosphoribosyl-1-pyrophosphate
Conditions | Yield |
---|---|
With Salmonella typhimurium OMP synthase wild type; magnesium chloride at 30℃; pH=8; Kinetics; Reagent/catalyst; aq. phosphate buffer; Enzymatic reaction; |
Conditions | Yield |
---|---|
With dihydroorotate dehydrogenase Enzymatic reaction; | |
With dihydroorotate dehydrogenase; coenzyme Q0 pH=8; Enzymatic reaction; |
chloro-trimethyl-silane
orotic acid
2,6-Bis-trimethylsilanyloxy-pyrimidine-4-carboxylic acid
Conditions | Yield |
---|---|
With 1,1,1,3,3,3-hexamethyl-disilazane Ambient temperature; | 99% |
Conditions | Yield |
---|---|
In acetonitrile at 25 - 75℃; Product distribution / selectivity; | 99% |
In water at 35 - 37℃; for 0.166667h; |
orotic acid
Conditions | Yield |
---|---|
Stage #1: orotic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 16h; Stage #2: acetyl 2,3-O-isopropylidene-α,β-ribofuranose With pyridine hydrochloride In acetonitrile at 20℃; | 98% |
orotic acid
Conditions | Yield |
---|---|
In acetone for 0.5h; Solvent; Reflux; | 98% |
4-[ethyl(dimethyl)ammonio]butanoate
orotic acid
3-carboxy-N-ethyl-N,N-dimethylpropan-1-aminium 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate
Conditions | Yield |
---|---|
In isopropyl alcohol | 97.4% |
orotic acid
Conditions | Yield |
---|---|
With triethylamine In water; dimethyl sulfoxide at 20 - 30℃; Temperature; Solvent; Reagent/catalyst; | 97% |
In methanol; water at 20 - 70℃; Solvent; | 85% |
Conditions | Yield |
---|---|
In water; acetone for 5h; Solvent; Reflux; | 96% |
orotic acid
Conditions | Yield |
---|---|
In acetonitrile at 60℃; for 5h; | 96% |
In ethanol at 65℃; | 5.5 g |
diazomethane
orotic acid
1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-6-carbonsaeuremethylester
Conditions | Yield |
---|---|
In methanol; diethyl ether at 0℃; | 95% |
In methanol Ambient temperature; | 93% |
AMD070
orotic acid
(S)-(N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl))-1,4-butanediamine orotate
Conditions | Yield |
---|---|
In methanol; water at 20℃; for 1h; | 95% |
orotic acid
5-nitroorotic acid
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 15 - 48℃; for 6h; Temperature; Cooling with ice; | 95% |
With sulfuric acid; nitric acid In water at 50 - 55℃; for 3h; | 90% |
Stage #1: orotic acid With sodium hydroxide In water for 3h; Stage #2: With sulfuric acid; nitric acid In water at 25 - 45℃; Inert atmosphere; | 88.6% |
With sulfuric acid; nitric acid In water at 50 - 55℃; |
orotic acid
5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylic acid
Conditions | Yield |
---|---|
With hydrazine hydrate In water at 90℃; for 5h; Temperature; | 95% |
orotic acid
Conditions | Yield |
---|---|
Stage #1: orotic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 16h; Stage #2: 1-O-benzoyl-2,3-O-isopropylidene-D-ribofuranoside With pyridine hydrochloride In acetonitrile at 20℃; for 4h; | 94% |
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 5℃; for 6h; Reflux; | 92.9% |
With hydrogenchloride for 24h; Fischer esterification; Heating; | 91% |
With hydrogenchloride | 90% |
orotic acid
α-chloroorotic acid
Conditions | Yield |
---|---|
Stage #1: orotic acid With iron(III) chloride; acetic anhydride; acetic acid at 90 - 95℃; Stage #2: With sulfuryl dichloride Reagent/catalyst; Temperature; Reflux; | 92% |
With hydrogenchloride; dihydrogen peroxide |
(2S,4E)-N-methyl-5-(5-isopropoxy-3-pyridyl)-4-penten-2-amine
orotic acid
Conditions | Yield |
---|---|
In ethanol Heating / reflux; | 91.4% |
orotic acid
Conditions | Yield |
---|---|
Stage #1: orotic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 16h; Stage #2: 1-O-pivaloyl-2,3-O-isopropylidene-D-ribofuranoside With pyridine hydrochloride In acetonitrile at 20℃; | 90% |
N-hydroxy-2-(4-(4-phenylbutyl)phenyl)acetamide
orotic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; | 90% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide | 90% |
Conditions | Yield |
---|---|
In toluene for 6h; Reflux; Inert atmosphere; Dean-Stark; | 90% |
orotic acid
Conditions | Yield |
---|---|
Stage #1: bis(2,2'-bipyridine)dichlororuthenium(II) dihydrate; orotic acid In ethanol at 125℃; for 2h; Sealed tube; Microwave irradiation; Stage #2: ammonium hexafluorophosphate In ethanol; water at 20℃; | 89% |
Conditions | Yield |
---|---|
Stage #1: orotic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In water; N,N-dimethyl-formamide for 0.0833333h; Stage #2: ethyl iodide In water; N,N-dimethyl-formamide at 60℃; for 5h; | 88% |
Stage #1: orotic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.0833333h; Stage #2: ethyl iodide In N,N-dimethyl-formamide at 60℃; for 5h; | 88% |
orotic acid
Conditions | Yield |
---|---|
In ethanol at 90℃; for 3h; | 88% |
Conditions | Yield |
---|---|
With 4-methyl-morpholine; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In N,N-dimethyl-formamide at 50 - 55℃; | 87% |
2,3-O-isopropylidene-D-ribofuranose
orotic acid
Conditions | Yield |
---|---|
With pyridine hydrochloride; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; | 87% |
Conditions | Yield |
---|---|
In diethyl ether; ethanol at 0 - 20℃; Reflux; | 85.4% |
orotic acid
((S)-2-amino-4-methylpentanoyl)-L-leucine methyl ester hydrochloride
orotyl-L-leucyl-L-leucine methyl ester
Conditions | Yield |
---|---|
With 4-methyl-morpholine; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In N,N-dimethyl-formamide at 50 - 55℃; | 85% |
furan-2-ylmethanamine
orotic acid
N-(furan-2-ylmethyl)-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxamide
Conditions | Yield |
---|---|
for 0.166667h; microwave irradiation; | 85% |
The Orotic acid, with the CAS registry number 65-86-1, is also known as 1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidecarboxylic acid. It belongs to the product category of Vitamin Ingredients. Its EINECS number is 200-619-8. This chemical's molecular formula is C5H4N2O4 and molecular weight is 156.10. What's more, its systematic name is 2,6-Dioxo-1,2,3,6-tetrahydro-4-pyrimidinecarboxylic acid. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Mutation data. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from moisture and mildew. It is a heterocyclic compound and an acid. Historically it was believed to be part of the Vitamin B complex and was called vitamin B13, but it is now known that it is not a vitamin. The compound is manufactured in the body by intestinal flora. It is sometimes used as a mineral carrier in some dietary supplements (to increase their bioavailability), most commonly for lithium orotate. This chemical is used in biochemical research, especially the biosynthesis of nucleic acids.
Physical properties of Orotic acid are: (1)ACD/LogP: -0.84; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.64; (4)ACD/LogD (pH 7.4): -4.56; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 6; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 95.5 Å2; (13)Index of Refraction: 1.568; (14)Molar Refractivity: 31.111 cm3; (15)Molar Volume: 95.051 cm3; (16)Polarizability: 12.333×10-24cm3; (17)Surface Tension: 68.58 dyne/cm; (18)Density: 1.642 g/cm3; (19)Flash Point: 351.1 °C; (20)Enthalpy of Vaporization: 101.63 kJ/mol; (21)Boiling Point: 656.9 °C at 760 mmHg; (22)Vapour Pressure: 3.76E-18 mmHg at 25°C.
Preparation: this chemical can be prepared by (2,5-dioxo-imidazolidin-4-ylidene)-acetic acid at the temperature of 64 °C. This reaction will need reagent 1 M aq. KOH with the reaction time of 3 hours. The yield is about 85%.
Uses of Orotic acid: it can be used to produce orotic acid N-hydroxysuccinimide ester at the ambient temperature. It will need reagent dicyclohexylcarbodiimide and solvent dimethylsulfoxide. The yield is about 76%.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It is harmful if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. You should not breathe dust. When using it, you need to wear suitable protective clothing, gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)\C1=C\C(=O)NC(=O)N1
(2)Std. InChI: InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
(3)Std. InChIKey: PXQPEWDEAKTCGB-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 841mg/kg (841mg/kg) | Drugs in Japan Vol. 6, Pg. 165, 1982. | |
mouse | LD50 | intravenous | 770mg/kg (770mg/kg) | Drugs in Japan Vol. 6, Pg. 165, 1982. | |
mouse | LD50 | oral | 2gm/kg (2000mg/kg) | Drugs in Japan Vol. 6, Pg. 165, 1982. |
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