Orotic acid

Modify Date: 2024-01-02 19:20:35

Orotic acid Structure
Orotic acid structure
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 Chinese USA Flash Point 351.1±34.3 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of Orotic acid


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].

 Names

Name orotic acid
Synonym More Synonyms

 Orotic acid Biological Activity

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
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
Stability Stable. Incompatible with strong oxidizing agents.
Water Solubility Slightly soluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RM3180000
CHEMICAL NAME :
Orotic acid
CAS REGISTRY NUMBER :
65-86-1
LAST UPDATED :
199701
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C5-H4-N2-O4
MOLECULAR WEIGHT :
156.11
WISWESSER LINE NOTATION :
T6MVMVJ FVQ

HEALTH HAZARD DATA

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

 Safety Information

Symbol GHS07
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

 Synthetic Route

 Articles56

More Articles
Solubilization of gliadins for use as a source of nitrogen in the selection of bacteria with gliadinase activity.

Food Chem. 168 , 439-44, (2014)

For patients with celiac disease, gliadin detoxification via the use of gliadinases may provide an alternative to a gluten-free diet. A culture medium, in which gliadins were the sole source of nitrog...

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

QSPR modeling of octanol/water partition coefficient for vitamins by optimal descriptors calculated with SMILES.

Eur. J. Med. Chem. 43 , 714-40, (2008)

Simplified molecular input line entry system (SMILES) has been utilized in constructing quantitative structure-property relationships (QSPR) for octanol/water partition coefficient of vitamins and org...

 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
Top Suppliers:I want be here





Get all suppliers and price by the below link:

Orotic acid suppliers


Price: $66/10mM*1mLinDMSO

Reference only. check more Orotic acid price