CAS Number65-86-1
SynonymsOrotonsan; orotic; Oropur; 2,6-dihydroxypyrimidine-4-carboxylic acid; Uracil-6-carboxylic acid; Orotic acid; [3H]-Orotic acid; vitamin B13; Oroturic; H-ORO-OH; Orotsaure; MFCD00006027; 1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidine carboxylic acid; EINECS 200-619-8; 2,6-Dioxo-1,2,3,6-tetrahydro-4-pyrimidinecarboxylic acid; 1,2,3,6-TETRAHYDRO-2,6-DIOXO-4-PYRIMIDINECARBOXYLIC ACID; 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid; Orotonin; Whey factor; Orotyl; Orodin; 6-Carboxyuracil; orodin[qr]; 6-uracilic acid; 1,2,3,6-Tetrahydro-2,6-dioxopyrimidine-4-carboxylic acid; Animal galactose factor
Molecular FormulaC5H4N2O4
Molecular Weight156.10
Purity≥98 (titration)%
Density1.8±0.1 g/cm3
Boiling Point656.9±65.0 °C at 760 mmHg
Melting Point≥300 °C
AppearanceWhite crystalline powder
EINECS200-619-8
Symbol
Signal WordWarning
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| Chemical & Physical Properties | |
|---|---|
| CAS Number | 65-86-1 |
| Catalog No. | 2A-9016926 |
| Chinese Name | 乳清酸 |
| Synonyms | Orotonsan; orotic; Oropur; 2,6-dihydroxypyrimidine-4-carboxylic acid; Uracil-6-carboxylic acid; Orotic acid; [3H]-Orotic acid; vitamin B13; Oroturic; H-ORO-OH; Orotsaure; MFCD00006027; 1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidine carboxylic acid; EINECS 200-619-8; 2,6-Dioxo-1,2,3,6-tetrahydro-4-pyrimidinecarboxylic acid; 1,2,3,6-TETRAHYDRO-2,6-DIOXO-4-PYRIMIDINECARBOXYLIC ACID; 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid; Orotonin; Whey factor; Orotyl; Orodin; 6-Carboxyuracil; orodin[qr]; 6-uracilic acid; 1,2,3,6-Tetrahydro-2,6-dioxopyrimidine-4-carboxylic acid; Animal galactose factor |
| Molecular Formula | C5H4N2O4 |
| Molecular Weight | 156.10 |
| Purity | ≥98 (titration) |
| Density | 1.8±0.1 g/cm3 |
| Boiling Point | 656.9±65.0 °C at 760 mmHg |
| Melting Point | ≥300 °C |
| Appearance | White crystalline powder |
| Water Solubility | Slightly soluble |
| Storage Condition | Food-grade plastic bag coated with kraft paper bag |
| Application | Orotic acid (OA) is an intermediate in the metabolism of pyrimidines. |
| EINECS | 200-619-8 |
| PubChem ID | 24897967 |
| MDL Number | MFCD00006027 |
| SMILES | OC(=O)C1=CC(=O)NC(=O)N1 |
| InChI | 1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11) |
| InChI Key | PXQPEWDEAKTCGB-UHFFFAOYSA-N |
| Beilstein/REAXYS | 383901 |
| NACRES Code | NA.51 |
| UNSPSC | 41106305 |
| Hazard Symbols | Transport |
| MSDS | msds/16926_1_65_86_1.pdf |
| Bioactivity | Orotic acid (OA) is an intermediate in pyrimidine metabolism.IC50 Value: Target: Nucleoside antimetabolite/analogin vitro: OA increases cell proliferation and decreases apoptosis in serum-starved SK-Hep1 hepatocellular carcinoma cells, which may ascribe to the inhibition of AMP-activated protein kinase (AMPK) phosphorylation and thus activation of mammalian target of rapamycin complex 1 (mTORC1) [1].in vivo: male Fischer 344 rats (130-150 g) to two-thirds PH in the absence or in the presence of OA (a 300-mg tablet of OA methyl ester implanted intraperitoneally at the time of two-thirds PH). treatment with OA resulted in a near-100% inhibition of RNR induced by two-thirds PH in rat liver, as monitored by enzyme activity and protein level [2]. The increases of hepatic OA and betaine levels in OA feeding rats was also found when compared to the normal rats [3]. Feeding 1% OA with diet decreased the phosphorylation of AMPK and increased the maturation of SREBP-1 and the expression of SREBP-responsive genes in the rat liver. OA-induced lipid accumulation was also completely inhibited by rapamycin. Mouse hepatocytes and mice were resistant to OA-induced lipogenesis because of little if any response in AMPK and downstream effectors [4]. Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog Natural Products >> Alkaloid Research Areas >> Cancer Target Human Endogenous Metabolite References [1]. Jung, E.J., K.Y. Lee, and B.H. Lee, Proliferating effect of orotic acid through mTORC1 activation mediated by negative regulation of AMPK in SK-Hep1 hepatocellular carcinoma cells. J Toxicol Sci, 2012. 37(4): p. 813-21. [2]. Manjeshwar, S., et al., The regulation of ribonucleoside diphosphate reductase by the tumor promoter orotic acid in normal rat liver in vivo. Mol Carcinog, 1999. 24(3): p. 188-96. [3]. Cha, J.Y., et al., Effect of betaine on the hepatic damage from orotic acid-induced fatty liver development in rats. J Enzyme Inhib Med Chem, 2011. [4]. Jung, E.J., et al., Role of the AMPK/SREBP-1 pathway in the development of orotic acid-induced fatty liver. J Lipid Res, 2011. 52(9): p. 1617-25. Chemical & Physical Properties Density 1.8±0.1 g/cm3 Boiling Point 656.9±65.0 °C at 760 mmHg Melting Point >300°C Molecular Formula C5H4N2O4 Molecular Weight 156.096 Flash Point 351.1±34.3 °C Exact Mass 156.017105 PSA 103.02000 LogP -1.40 Vapour Pressure 0.0±2.1 mmHg at 25°C Index of Refraction 1.705 InChIKey PXQPEWDEAKTCGB-UHFFFAOYSA-N SMILES O=C(O)c1cc(=O)[nH]c(=O)[nH]1 Stability Stable. Incompatible with strong oxidizing agents. Water Solubility Slightly soluble |
| Use of | Properties Articles56 Name orotic acid Synonym More Synonyms Orotic acid Biological Activity Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog Natural Products >> Alkaloid Research Areas >> Cancer Human Endogenous Metabolite References [1]. Jung, E.J., K.Y. Lee, and B.H. Lee, Proliferating effect of orotic acid through mTORC1 activation mediated by negative regulation of AMPK in SK-Hep1 hepatocellular carcinoma cells. J Toxicol Sci, 2012. 37(4): p. 813-21. [2]. Manjeshwar, S., et al., The regulation of ribonucleoside diphosphate reductase by the tumor promoter orotic acid in normal rat liver in vivo. Mol Carcinog, 1999. 24(3): p. 188-96. [3]. Cha, J.Y., et al., Effect of betaine on the hepatic damage from orotic acid-induced fatty liver development in rats. J Enzyme Inhib Med Chem, 2011. [4]. Jung, E.J., et al., Role of the AMPK/SREBP-1 pathway in the development of orotic acid-induced fatty liver. J Lipid Res, 2011. 52(9): p. 1617-25. Chemical & Physical Properties Molecular Formula C5H4N2O4 Exact Mass 156.017105 PSA 103.02000 LogP -1.40 Index of Refraction 1.705 InChIKey PXQPEWDEAKTCGB-UHFFFAOYSA-N Stability Stable. Incompatible with strong oxidizing agents. Water Solubility Slightly soluble |
| Transport Info | Product name: Purity: 99.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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