Orotic Acid 乳清酸,无水

CAS 65-86-1 MFCD00006027

化学结构图

65-86-1
SMILES: O=C(O)c1cc(=O)[nH]c(=O)[nH]1

化学属性

Mol. FormulaC5H4N2O4
Mol. Weight156.10
Density1.642
Melting Point345-346°C
TSCAYes
Appearance 白色结晶性粉末。mp345-346℃ (分解)。在水中难溶解(0.18%),在沸水中溶解度为13%,极微溶于醇及有机溶剂,不溶于醚。遇碱成盐溶解。最大吸收波长282nm。
SolubilitySlightly soluble
Boiling Point656.9°C at 760 mmHg
Flash Point351.1°C

别名和识别编码

Chemical NameOrotic Acid
Synonym Orotic acid {LY} Orotic acid {} {LY} Orotic acid {} {} {LY} Orotic acid {} {} {} {LY} Orotic acid {} {} {} {} {LY} Orotic acid {} {} {} {} {} {LY} Orotic acid {} {} {} {} {} {} {LY} Orotic acid {} {} {} {} {} {} {} {LY} Orotic acid {} {} {} {} {} {} {} {} {LY} Orotic acid {} {} {} {} {} {} {} {} {} {LY} Orotic acid {} {} {} {} {} {} {} {} {} {} {LY} Orotic acid {} {} {} {} {} {} {} {} {} {} {} {LY} Orotic acid {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {LY} Orotic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Orotic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Orotic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Orotic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Orotic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
MDL NumberMFCD00006027
CAS Number65-86-1
EC Number200-619-8
Beilstein Registry Number383901
PubChem Substance ID87574079
Merck Number6876
Alfabeta NameDIOXOTETRAHYDROPYRIMIDINECARBOXYLICACID 2612364-----,,,,
Chemical Name Translation乳清酸,无水
Reaxys-RN383901
Wiswesser Line NotationT6MVMVJ FVQ
LabNetwork Molecule IDLN00010361
Canonical SMILESO=C(C(NC1=O)=CC(N1)=O)O
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分类

  • {SNA} Metabolic Pathways, Metabolites and Cofactors on the Metabolic Pathways Chart, Metabolomics, Nucleotide, Nutrition Research, Other Biochemical, Phytochemicals by Chemical Classification
  • {SNA} Nucleotide, Other Biochemical, Phytochemicals by Chemical Classification, 代谢组学, 代谢通路, 代谢通路图中的代谢产物和辅酶分子, 细胞生物学, 营养研究
  • {Chemicalbook} 生物化学品: 核酸类: 核酸碱基及其衍生物
  • {SNA} Metabolic Pathways, Metabolites and Cofactors on the Metabolic Pathways Chart, Nucleotide, Other Biochemical, Phytochemicals by Chemical Classification, 代谢组学, 细胞生物学, 营养研究

产品应用

  • 生化研究。合成核酸。化妆品配制。

相关文献及参考

  • [2]. Staretz-Chacham O, et, al. The role of orotic acid measurement in routine newborn screening for urea cycle disorders. J Inherit Metab Dis. 2020 Nov 15.
  • [3]. Durschlag RP, et, al. Orotic acid-induced metabolic changes in the rat. J Nutr. 1980 Apr;110(4):816-21.
  • Merck: 14,6876
  • Merck: 14,6876 Beilstein: 25,IV,1759
  • [1]. Löffler M, et, al. Orotate (orotic acid): An essential and versatile molecule. Nucleosides Nucleotides Nucleic Acids.
  • [1]. Löffler M, et, al. Orotate (orotic acid): An essential and versatile molecule. Nucleosides Nucleotides Nucleic Acids.
  • [2]. Staretz-Chacham O, et, al. The role of orotic acid measurement in routine newborn screening for urea cycle disorders. J Inherit Metab Dis. 2020 Nov 15.
  • [3]. Durschlag RP, et, al. Orotic acid-induced metabolic changes in the rat. J Nutr. 1980 Apr;110(4):816-21.

安全信息

Signal word Warning
GHS Symbol
WGK Germany3
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P301+P312+P330
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P332+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H302 Harmful if swallowed 吞食有害
  • H319 Causes serious eye irritation 严重刺激眼睛
RTECSRM3180000
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Warnings IRRITANT
Hazard Codes Xn
Storage condition 2-8°C {LY} 2-8°C {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {
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
REFERENCE :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: 6,165,1982

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
REFERENCE :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: 6,165,1982

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
REFERENCE :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: 6,165,1982

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

TYPE OF TEST            : Phage inhibition capacity
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 1 gm/L
REFERENCE :
   ZAPOAK Zeitschrift fuer Allgemeine Mikrobiologie.  (Akademie-Verlag GmbH,
   Postfach 1233, Berlin DDR-1086 Ger. Dem. Rep.)  V.1-    1960-
   Volume(issue)/page/year: 12,583,1972

TYPE OF TEST            : DNA inhibition
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 14 gm/kg/14D (Continuous)
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

TYPE OF TEST            : Morphological transformation
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 25200 mg/kg/6W
REFERENCE :
   CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House,
   Southfield Road, Eynsham, Oxford OX8 1JJ, UK)  V.1-    1980-
   Volume(issue)/page/year: 9,387,1988

其他信息

  • 用途一:主要用于日用化妆品及医药、核酸、生物研究,医药上用于制黄胆肝药、心脏病药物等
  • 乳清酸尿症:乳清酸尿症是由于遗传性乳清酸磷酸核糖基转移酶与乳清酸核苷磷酸脱羧酶缺陷引起的嘧啶代谢障碍病,为罕见的常染色体隐性遗传病。患儿出生时无异常,生后2~6月开始逐渐出现体格及智能发育落后。伴面色苍白、蓝色巩膜、斜视、肌张力低及脾肿大,周围血呈巨幼红细胞性贫血、白细胞低下。骨髓检查:红、粒细胞系均有巨幼细胞改变。尿中乳清酸量增高达400~1400mg/24h(成人正常值约为1~4mg/24h),尿液稍冷后即呈明显混浊,内有针状结晶;结晶尿有时可致尿路阻塞。每天用大剂量尿嘧啶治疗(150mg/kg),可迅速解除贫血及乳清酸尿; 尿中乳清酸含量的降低提示在嘧啶生物合成过程中,乳清酸的合成受负反馈机制的调节。 上述二种酶在多数患者的肝细胞、白细胞及培养的成纤维细胞中同时缺乏。但也曾有脱羧酶单独缺乏的报道,此类患者的临床表现与上述转移酶及脱羧酶同时缺乏者无差别。近来资料提示乳清酸磷酸核糖基转移酶和乳清酸核苷磷酸脱羧酶的同时缺陷,乃因它们有共同的亚单位并受一个基因控制。目前可用多种方法测定酶活力,协助确诊及产前诊断。
  • 存在于乳中,系动物组织中嘧啶的前体。在100ml水中能溶解0.18g,100ml沸水中能溶解13g,极微溶于醇及有机溶剂,不溶于乙醚和氯仿。(无水)、334℃(一水)。最大吸收波长282nm,最小吸收波长255nm。
  • 上游原料:硫酸 --> 乙酸 --> 尿素 --> 草酸二乙酯 --> 重铬酸钠 --> 二氧化硒 --> 乙氧基甲叉丙二酸二乙酯 --> 2,4-二羟基-6-甲基嘧啶 --> 1,3-二苄基咪唑-2-酮-4,5-二羧酸
  • 用途二:维生素类药。适用于高尿酸血症、高胆固醇血症、慢性肝炎、肝硬化。也可用作抗贫血和营养强壮剂。大剂量可诱发脂肪肝。急性期肝炎、白血病、恶性肿瘤患者忌用。
  • 用途四:生化研究。合成核酸。化妆品配制。
  • Sigma Aldrich:65-86-1(sigmaaldrich)
  • 用途三:乳清酸是一种营养药,也称维生素B13。该品与5-氨基咪唑-4-羧酰胺在90℃成盐,则得到氨咪酰胺乳清酸盐(C9H10N6O5·2H2O,[2574-78-9])。这两种药物都是保肝药。
  • Alfa Aesar:无水乳清酸,97% Orotic acid, anhydrous, 97%(65-86-1)
  • 概述:乳清是作为干酪工业副产品而产生的,是从制造干酪和干酪素的凝乳中分离出来的清液或浆液。牛乳中乳清含量达到80%~90%,含有原料乳营养成分的50%。从硬质及半硬质、软质干酪和凝乳酶干酪素生产中获得的副产品的甜乳清pH为5.9~6.4。从无机酸沉淀制造干酪素中所得到的酸乳清的pH为4.3~4.6。 人们可以将乳清浓缩、干燥、分离成各种成分,如蛋白质、乳糖、矿物质、脂肪及它们的复合物,作为食品加工用原料。目前常用的乳清制品有乳清粉和乳清浓缩蛋白 (WPC)。 乳清酸是一种营养药,又名维生素B13,但不是维生素,是从水中得白色有光泽的针状晶体或结晶性粉末,无臭,有酸味。熔点345~346℃。难溶于冷水和乙醇及有机溶剂,微溶于热水,不溶于醚。与过氧化氢和浓盐酸作用生成5-氯尿嘧啶-4-羧酸。可由草酸二乙酯与乙酸乙酯缩合成丁酮酸二乙酯,用脲素环合后得到5-乙氧羰基甲叉乙内酰脲,再经水解、扩环、酸析而得。医药上可用于制保肝药,可以治疗黄疸病和一般肝脏机能障碍病。
  • 方法一:由草酸二乙酯经与乙酸缩合、与尿素环合得到5-乙氧羰基甲叉乙内酰脲,再经扩环、酸析而得乳清酸。
  • 图谱信息:乳清酸(65-86-1)质谱(MS) 乳清酸(65-86-1)核磁图( 1 HNMR) 乳清酸(65-86-1)红外图谱(IR1) 乳清酸(65-86-1)红外图谱(IR2)
  • 下游产品:2,6-二氯嘧啶-4-甲酸甲酯 --> 海因 --> 2,4-二甲氧基嘧啶-6-甲酸 --> 5-氨基乳清酸 --> 乳清酸 --> 阿卡明
  • F:10-21
  • 检测方法:NMR,HPLC
  • MOL 文件:65-86-1.mol
  • Hazard Note:Harmful

系列性分类


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