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65-86-1

Basic Information
CAS No.: 65-86-1
Name: Orotic acid
Article Data: 66
Molecular Structure:
Molecular Structure of 65-86-1 (Orotic acid)
Formula: C5H4N2O4
Molecular Weight: 156.098
Synonyms: Orotic acid(8CI);1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid;2,4-Dihydroxypyrimidine-6-carboxylic acid;2,6-Dihydroxy-4-pyrimidinecarboxylicacid;2,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid;6-Carboxyuracil;6-Uracilcarboxylic acid;Animal galactose factor;NSC 79560;NSC 9791;Orodin;Orotonin;Oroturic;Orotyl;Vitamin B13;Whey factor;
EINECS: 200-619-8
Density: 1.642 g/cm3
Melting Point: 345-346 °C
Boiling Point: 656.9 °C at 760 mmHg
Flash Point: 351.1 °C
Solubility: slightly soluble in water, very slightly soluble in alcohol and organic solvents, insoluble in ether
Appearance: white crystalline powder
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-36/37/38
Safety: 26-36/37/39-22
PSA: 103.02000
LogP: -1.23860
Synthetic route
626-48-2

6-Methyluracil

65-86-1

orotic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); oxygen; cobalt(II) acetate; acetic acid at 80℃; for 15h;92%
With potassium hydroxide; potassium hexacyanoferrate(III)
461-72-3

2,4-imidazolidinedione

298-12-4

Glyoxilic acid

65-86-1

orotic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 115 - 120℃; for 2h; Temperature; Large scale;91.9%
153816-00-3

(2Z)-(2,5-dioxoimidazolidin-4-ylidene)acetic acid

65-86-1

orotic acid

Conditions
ConditionsYield
With potassium hydroxide at 64℃; for 3h;85%
With potassium hydroxide at 64℃; for 3h; Mechanism; Kinetics; var. conc. of KOH;85%

C5H6N2O4

65-86-1

orotic acid

Conditions
ConditionsYield
With oxygen; palladium dichloride In N,N-dimethyl-formamide at 80℃; under 760.051 Torr; for 36h; Reagent/catalyst; Solvent; Pressure; Temperature;85%
496-46-8

glycoluril

65-86-1

orotic acid

Conditions
ConditionsYield
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%
36327-91-0

orotoaldehyde

A

22126-44-9

6-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione

B

65-86-1

orotic acid

Conditions
ConditionsYield
With potassium hydroxide
36327-91-0

orotoaldehyde

65-86-1

orotic acid

Conditions
ConditionsYield
With sodium dichromate; sulfuric acid
16953-46-1

6-oxo-2-thioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbaldehyde

65-86-1

orotic acid

Conditions
ConditionsYield
With sodium dichromate; sulfuric acid
Multi-step reaction with 2 steps
1: aqueous KOH
2: aqueous alkali .H2O2
View Scheme
6953-78-2

2-thioorotic acid

65-86-1

orotic acid

Conditions
ConditionsYield
With alkali .H2O2
4628-39-1

6-carboxymethyluracil

65-86-1

orotic acid

Conditions
ConditionsYield
With potassium hydroxide; potassium hexacyanoferrate(III) 22 d;
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Reported in EPA TSCA Inventory.

Specification

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%.

Orotic acid can be prepared by (2,5-dioxo-imidazolidin-4-ylidene)-acetic acid at the temperature of 64 °C

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%.

Orotic acid can be used to produce orotic acid N-hydroxysuccinimide ester at the ambient temperature

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.