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6-Methyluracil

6-Methyluracil structure

6-Methyluracil 

structure
  • CAS No:

    626-48-2

  • Formula:

    C5H6N2O2

  • Chemical Name:

    6-Methyluracil

  • Synonyms:

    2,4(1H,3H)-Pyrimidinedione,6-methyl-;Uracil,6-methyl-;6-Methyl-2,4(1H,3H)-pyrimidinedione;6-Methyluracil;Pseudothymine;2,4-Dihydroxy-6-methylpyrimidine;AWD 23-15;K 4;NSC 9456;6-Methylpyrimidine-2,4-diol;2-Hydroxy-6-methyl-1,4-dihydropyrimidin-4-one;2-Hydroxy-6-methyl-3,4-dihydropyrimidin-4-one;15985-99-6;78334-35-7

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

Description

White to Off-White Crystalline Solid


6-methyluracil is a pyrimidone that is uracil with a methyl group at position 6. It has a role as a metabolite. It derives from a uracil.

6-Methyluracil Basic Attributes

126.11

126.11

115647

210-949-4

5O052W0G6I

9456

DTXSID8052308

CRYSTALS FROM GLACIAL ACETIC ACID|OCTAHEDRAL PRISMS OR NEEDLES FROM WATER OR ALCOHOL

29335995

Characteristics

58.2

-0.8

White to almost white Fine Crystalline Powder

1.2±0.1 g/cm3

275 °C (decomp)

420.4°C at 760 mmHg

208ºC

1.490

H2O: 7 g/L (22 ºC);SOL IN WATER, ETHER, ALKALI, AMMONIA, HOT ALCOHOL

Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

LD50 oral in rat: 64500mg/kg

AQ SOLN 13

DECOMP ABOVE 300 °C|UV: 6-43 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /Uracil, 1-methyl/|UV: 6-43 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /Uracil, 3-methyl/

Safety Information

II

8

1759

3

62-63

36/37/39-45-36/37

YR0700000

Xn

Stable under normal temperatures and pressures.

P281

H361

|Warning|H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]|P201, P202, P281, P308+P313, P405, and P501|Aggregated GHS information provided by 45 companies from 3 notifications to the ECHA C&L Inventory.

Toxicity

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.

Drug Information

Anti-ulcer Agents; Radiation-protective Agents; Adjuvants, Immunologic|EXPTL USE: 4-METHYLURACIL (50 MG/KG/DAY) SHOWED SIGNIFICANT ANTIMETASTATIC EFFECTS WHEN ADMIN ORALLY TO RATS WITH LYMPHO- OR LYMPHOHEMATOGENIC METASTASES OF PLISS LYMPHOSARCOMA OR WALKER CARCINOSARCOMA FOR 3 DAYS BEFORE & AFTER LAPAROTOMY.

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. (See all compounds classified as Adjuvants, Immunologic.)|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. (See all compounds classified as Anti-Ulcer Agents.)|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. (See all compounds classified as Radiation-Protective Agents.)

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.

6-methyluracil

6-Methyluracil Use and Manufacturing

Methods of Manufacturing

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).

Uses

Used in the pharmaceutical industry, mainly for the synthesis of the cardiovascular drug pansentine

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.

DISSOCIATION CONSTANTS OF 6-SUBSTITUTED THIOURACILS & URACILS, INCLUDING 6-METHYLURACIL, WERE DETERMINED BY A SPECTROPHOTOMETRIC METHOD. PK1 VALUES OF THIOURACILS WERE LOWER THAN THOSE OF CORRESPONDING URACILS.

Computed Properties

Molecular Weight:126.11
XLogP3:-0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:126.042927438
Monoisotopic Mass:126.042927438
Topological Polar Surface Area:58.2
Heavy Atom Count:9
Complexity:195
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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