6-Methyluracil

HCID 12283

Basic information

CAS
626-48-2
Standard SMILES
Cc1cc(=O)[nH]c(=O)[nH]1
InChIKey
SHVCSCWHWMSGTE-UHFFFAOYSA-N
Molecular formula
C5H6N2O2
Average molar mass
126.11 g/mol
Monoisotopic mass
126.04292743

Overview

6-methyluracil is a pyrimidone that is uracil with a methyl group at position 6. It has a role as a metabolite. It is functionally related to a uracil.

Names & identifiers

Preferred name
6-Methyluracil
IUPAC
6-methyl-1H-pyrimidine-2,4-dione
English name
6-Methyluracil
Molecular formula
C5H6N2O2
Molecular weight
126.11

Names & synonyms

6-METHYLURACIL626-48-2Pseudothymine4-Methyluracil6-Methyl-1H-pyrimidine-2,4-dione6-Methyl-2,4(1H,3H)-pyrimidinedione2,4(1H,3H)-Pyrimidinedione, 6-methyl-Uracil, 6-methyl-DTXSID8052308CHEBI:747335O052W0G6INSC-9456
Show more names
6-METHYL-1,2,3,4-TETRAHYDROPYRIMIDINE-2,4-DIONEMetacylMetacilMethacylMethacilNSC 9456Awd 23-15
DTXCID9030880AWD-23-15RefChem:105068210-949-4Methyluracil2,4-Dihydroxy-6-methylpyrimidine6-methylpyrimidine-2,4(1H,3H)-dione6-methylpyrimidine-2,4-diol

Database identifiers

CAS
626-48-2
PubChem CID
12283
DTXSID
DTXSID8052308
ChEMBL
CHEMBL1650614
ChEBI
CHEBI:74733
UNII
5O052W0G6I
EC Number
210-949-4
Nikkaji
J39.643E

Properties

Computed structural properties

XLogP
-0.8
Topological polar surface area
58.2 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
9

Experimental & physicochemical properties

pHAQ SOLN 13
SpringerMaterials PropertiesBoiling point
LogP-0.77
Color/Form · 2 items

CRYSTALS FROM GLACIAL ACETIC ACID

OCTAHEDRAL PRISMS OR NEEDLES FROM WATER OR ALCOHOL

SolubilitySOL IN WATER, ETHER, ALKALI, AMMONIA, HOT ALCOHOL
Collision Cross Section120.5 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID8052308]

Physicochemical properties

Melting point
318 °C · 318 °C (dec.)(lit.)
Density
1.226 · 1.226±0.06 g/cm3(Predicted)
storage temp.
Inert atmosphere,Room Temperature
solubility
DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
form
Fine Crystalline Powder
pka
1 · pK1:9.52 (25°C)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 5 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 2 items

Chemical: 2,4(1H,3H)-Pyrimidinedione, 6-methyl-

6-Methyluracil: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesRepr. 2 (100%)

Toxicology

Interactions · 1 item

XYLOL (43.46 MG/CU M), TOLUENE (24.28 MG/CU M), OR BUTYL ACETATE (209.91 MG/CU M) INHALED 5 HR DAILY FOR 4 MONTHS DECREASED SERUM ALBUMIN & INCREASED SERUM BETA- & GAMMA-GLOBULIN & BETA-LIPOPROTEIN LEVELS IN RATS. 4-METHYLURACIL ADDED TO FOOD OF RATS DURING INHALATION NORMALIZED THE LIPID & PROTEIN METABOLIC INDEXES. PROPHYLACTIC USE OF THESE PREPN IN TANNING INDUSTRY WORKERS IS SUGGESTED.

Non-Human Toxicity Excerpts · 5 items

...INJECTED CHICK EGGS WITH 4 MG...PRODUCED ABNORMALITIES OF BRAIN OR EYE IN 24%. NO DEFECTS WERE PRODUCED IN RAT FETUSES WHEN THE MOTHER RECEIVED 3000 MG/KG OF BODY WEIGHT ON THE 9TH & 10TH DAY OF GESTATION.

6-METHYLURACIL INHIBITED GERMINATION OF CICER ARIETINUM SEEDS (A SYSTEM USED TO SIMULATE EMBRYONIC TISSUE).

WITH AN AGAR DIFFUSION TEST, IT WAS SHOWN THAT THERE ARE SUBSTANCES WITH STIMULATING OR INHIBITING ACTION, RESPECTIVELY, ON THE INDUCIBILITY OF PROPHAGES. THE PROPHAGES (LAMBDA +) & (LAMBDA IND S) EXHIBIT DIFFERENT REACTIONS ON EXPOSURE OF RESPECTIVE LYSOGENIC STRAINS AGAINST SOME SUBSTANCES TESTED. A SMALL SELECTION OF EFFECTIVE SUBSTANCES WERE QUALITATIVELY TESTED ON THE NONLYSOGENIC STRAIN ESCHERICHIA COLI C600 T44 & ON THE LYSOGENIC COMPLEX ESCHERICHIA COLI C600 T44 (LAMBDA IND-), THE PROPHAGE OF WHICH IS KNOWN TO BE NOT INDUCIBLE BY UV LIGHT. 6-METHYLURACIL DID NOT INDUCE (LAMBDA +) OR (LAMBDA IND S) PROPHAGES IN ESCHERICHIA COLI C600 T44 STRAINS.

6-METHYLURACIL ADMIN ORALLY TO RATS AT 50 MG/KG DAILY FOR 30 DAYS INCR MUSCLE MITOCHONDRIAL PROTEIN CONTENT, SOMEWHAT INCREASED OXYGEN CONSUMPTION & PHOSPHATE DEMINERALIZATION, BUT DID NOT AFFECT OXIDATIVE PHOSPHORYLATION DURING MUSCULAR EXERCISE.

For more Non-Human Toxicity Excerpts (Complete) data for 6-METHYLURACIL (9 total), please visit the HSDB record page.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
YR0700000
ridadr
1759
hs_code
29335995

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 3 items

UNCHANGED 6-METHYL-2-THIOURACIL (46% OF DOSE), 6-METHYLURACIL (9%), 6-METHYL-2-METHYLTHIOURACIL (2%), 6-METHYL-4-OXOPYRIMIDINE (2%), 2-AMINO-6-METHYL-4-OXOPYRIMIDINE (0.2%), & UREA (1%) WERE EXCRETED IN URINE OF RATS THAT HAD BEEN TREATED ORALLY WITH 6-METHYL-2-THIOURACIL.

...STUDIES INDICATED THE FORMATION OF FOUR VOLATILE SUBSTANCES AFTER IRRADIATION OF A 10 PPM AQ BROMACIL SOLN FOR 6 DAYS. THE MAJOR PRODUCT (37%) WAS 6-METHYLURACIL.

A MIXED CULTURE OF PSEUDOMONAS SPECIES & PROACTINOMYCES RUBER UTILIZED 6-METHYLURACIL AS THE SOLE SOURCE OF CARBON & NITROGEN. 6-METHYLURACIL WAS OXIDATIVELY CONVERTED TO URACIL WHICH WAS SUBSEQUENTLY METABOLIZED TO BARBITURIC ACID & UREA.

MeSH Pharmacological Classification · 3 items

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity.

Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief.

Drugs used to protect against ionizing radiation. They are usually of interest for use in radiation therapy but have been considered for other purposes, e.g. military.

Uses & manufacturing

Methods of Manufacturing · 2 items

BOESE, US PATENT 2,138,756 (1938 TO CARBIDE & CARBON CHEM); GLEASON, US PATENT 2,174,239 (1939 TO STANDARD OIL). SYNTHESIS FROM UREA & ETHYL ACETOACETATE: DONLEAVY, KISE, ORG SYN 17, 63 (1937); BY ISOMERIZATION OF 2-HYDROXY-4-METHOXY-6-METHYLPYRIMIDINE: MCOMIE ET AL, J CHEM SOC 1957, 1830...

...FROM UREA & DIKETENE: KHROMOV-BORISOV, KARLINSKAYA, J GEN CHEM USSR 26, 1728 (1956); USSR PATENT 101,690 (1955), CA 51, 12989F (1957).

General Manufacturing Information · 3 items

2,4(1H,3H)-Pyrimidinedione, 6-methyl-: ACTIVE

6-METHYLURACIL AT 100 PPM INCREASED THE INTENSITY OF PROTEIN SYNTHESIS IN PINTO BEANS BY 47.2%, AS COMPARED TO 87% & 37.3% FOR BENZYLADENINE (30 PPM) & BENZIMIDAZOLE (200 PPM). LONG-TERM TREATMENT OF PINTO BEANS WITH 100 PPM INCREASED CHLOROPHYLL CONTENT IN LEAVES, COMPARED TO UNTREATED INTACT LEAVES. 6-METHYLURACIL STIMULATED RNA SYNTHESIS IN TOBACCO LEAF BY 50%, AS COMPARED TO 21% & 23% FOR SODIUM BETA-URAMINE CROTONATE & ETHYL BETA-URAMINE CROTONATE RESPECTIVELY.

WHEN APPLIED AS SALVE TO SKIN OF VOLUNTEERS, 6-METHYLURACIL PARTIALLY PROTECTED AGAINST ULTRAVIOLET-INDUCED ERYTHEMA.

Applications

Uses6-Methyluracil (cas# 626-48-2) is a compound useful in organic synthesis.

Preparation methods

Preparation6-Methyluracil [626-48-2]. is produced by condensation of diketene with urea. It is used in the production of the analgesic mepirizole, the feed additive orotic acid, and 5-aminoorotic acid.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]

Additional notes

DefinitionChEBI: A pyrimidone that is uracil with a methyl group at position 6.

Related reactions

23 records

Compound notes

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