CAS 65-86-1|Orotic acid
| Common Name | Orotic acid | ||
|---|---|---|---|
| CAS Number | 65-86-1 | Molecular Weight | 156.096 |
| Density | 1.8±0.1 g/cm3 | Boiling Point | 656.9±65.0 °C at 760 mmHg |
| Molecular Formula | C5H4N2O4 | Melting Point | >300°C |
| MSDS | ChineseUSA | Flash Point | 351.1±34.3 °C |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | orotic acid |
|---|---|
| Synonym | More Synonyms |
Orotic acid BiologicalActivity
| Description | 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/AnalogNatural Products >>AlkaloidResearch 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 |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 2 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 841 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 770 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- Morphological transformation
- TYPE OF TEST :
- DNA inhibition
MUTATION DATA - TYPE OF TEST :
- DNA inhibition
- TEST SYSTEM :
- Rodent - rat Liver
- DOSE/DURATION :
- 120 umol/L
- REFERENCE :
- CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 9,675,1988
- TYPE OF TEST :
- DNA inhibition
- TEST SYSTEM :
- Rodent - rat Liver
- DOSE/DURATION :
- 120 umol/L
- REFERENCE :
- CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 9,675,1988
Safety Information
| Symbol | GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302-H315-H319-H335 |
| Precautionary Statements | P261-P305 + P351 + P338 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xn:Harmful |
| Risk Phrases | R22;R36/37/38 |
| Safety Phrases | S26-S36/37/39-S22 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | RM3180000 |
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Synonyms
| Orotonsan |
| orotic |
| Oropur |
| 2,6-dihydroxypyrimidine-4-carboxylic acid |
| Uracil-6-carboxylic acid |
| Orotic acid |
| [3H]-Orotic acid |
| vitamin B13 |
| Oroturic |
| 4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo- |
| 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 |
