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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 195
実験および物理化学的性質
Color/Form
CRYSTALS FROM GLACIAL ACETIC ACID
OCTAHEDRAL PRISMS OR NEEDLES FROM WATER OR ALCOHOL
Other Experimental Properties
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/
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
- 色
- 白~ほぼ白
- 水溶解度
- 7 g/L · 7g/L(22℃)
- Merck
- 14 · 14,6133
- BRN
- 115647 · 115647
- InChI
- InChI=1S/C5H6N2O2/c1-3-2-4(8)7-5(9)6-3/h2H,1H3,(H2,6,7,8,9)
- InChIKey
- SHVCSCWHWMSGTE-UHFFFAOYSA-N
- SMILES
- C1(=O)NC(C)=CC(=O)N1
- CAS データベース
- 626 · 626-48-2(CAS DataBase Reference)
- NISTの化学物質情報
- 6 · 6-Methyluracil(626-48-2)
- EPAの化学物質情報
- 2 · 2,4(1H,3H)-Pyrimidinedione, 6-methyl- (626-48-2)
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
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
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
毒性情報
Interactions
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
...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
- risk_code
- 62-63
- 化審法
- (5)-934
- hazard_code
- Xn
- safety_code
- 36/37/39-45-36/37
- hazard_class
- 8
- packing_group
- II
- Hazard Classifications
- Repr. 2
- ストレージクラス
- 11 - Combustible Solids
- 有毒物質データの
- 626-48-2(Hazardous Substances Data)
化学と産業
薬理情報
Metabolism/Metabolites
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
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
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
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.]
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義ChEBI: A pyrimidone that is uracil with a methyl group at position 6.
関連反応
関連ノート
読み込み中…