6-メチルウラシル

6-Methyluracil

HCID 12283CAS 626-48-2

基本情報

標準SMILES
Cc1cc(=O)[nH]c(=O)[nH]1
InChIKey
SHVCSCWHWMSGTE-UHFFFAOYSA-N
分子式
C5H6N2O2
平均分子量
126.11 g/mol
単同位体質量
126.04292743

概要

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.

名称と識別子

優先名称
6-Methyluracil
IUPAC
6-methyl-1H-pyrimidine-2,4-dione
現地名
6-メチルウラシル
英語名
6-Methyluracil
分子式
C5H6N2O2
分子量
126.11

名称と別名

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
名称をさらに表示
6-メチルウラシル6-メチルピリミジン-2,4(1H,3H)-ジオンプソイドチミン2,4-ジヒドロキシ-6-メチルピリミジン6-メチルピリミジン-2,4-ジオール2,4-ジヒドロキシ-6-メチルピリミジン 6-メチルウラシル2,4‐ジヒドロキシ‐6‐メチルピリミジン6-メチル-2,4(1H,3H)-ピリミジンジオン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

データベース識別子

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

物性

構造計算による物性

XLogP
-0.8
極性表面積
58.2 Ų
水素結合供与体数
2
水素結合受容体数
2
回転可能結合数
0
重原子数
9

実験および物理化学的性質

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

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]

物理化学的性質

融点
318 °C · 318 °C (dec.)(lit.)
比重(密度)
1.226 · 1.226±0.06 g/cm3(Predicted)
貯蔵温度
Inert atmosphere,Room Temperature
溶解性
DMSO(わずかに)、メタノール(わずかに、加熱、超音波処理)
酸解離定数(Pka)
1 · pK1:9.52 (25°C)
外見
微結晶性粉末

化学的性質

化学的特性White to Off-White Crystalline Solid

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Regulatory Information · 2 件

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%)

毒性情報

Interactions · 1 件

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 件

...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.

安全データ

wgk
3
tsca
TSCA listed
rtecs
YR0700000
ridadr
1759
毒性
LD50 oral in rat: 64500mg/kg
hs_code
29335995

化学と産業

薬理情報

Metabolism/Metabolites · 3 件

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 件

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.

用途と製造

Methods of Manufacturing · 2 件

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 件

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.

応用分野

用途有機合成原料。

使用6-Methyluracil (cas# 626-48-2) is a compound useful in organic synthesis.

調製方法

製造方法6-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.

純化方法Crystallise 6-methyluracil from EtOH or acetic acid. [Beilstein 24 III/IV 1281.]

サプライヤー50 社

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補足説明

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

関連反応

23 件

関連ノート

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