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thiamin chloride hydrochloride | 59-43-8

中文名称
——
中文别名
——
英文名称
thiamin chloride hydrochloride
英文别名
3-((4-Ammonio-2-methylpyrimidin-5-yl)methyl)-5-(2-hydroxyethyl)-4-methylthiazol-3-ium chloride;2-[3-[(4-amino-2-methylpyrimidin-1-ium-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol;chloride
thiamin chloride hydrochloride化学式
CAS
59-43-8
化学式
C12H18N4OS*2Cl
mdl
——
分子量
337.273
InChiKey
MYVIATVLJGTBFV-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    248 °C (decomp)
  • 密度:
    1.3175 (rough estimate)
  • 溶解度:
    二甲基亚砜:6 mg/mL(19.95 mM)
  • LogP:
    -3.930 (est)
  • 颜色/状态:
    Crystals from water
  • 气味:
    SLIGHT, CHARACTERISTIC
  • 蒸汽压力:
    1.8X10-10 mm Hg at 25 °C (est)
  • 稳定性/保质期:
    Canned vegetables and fruits stored for 1 yr at 65 °F show low losses of thiamine; at 80 °F losses are 15-25%
  • 分解:
    When heated to decomposition it emits very toxic fumes of /nitric oxide/, /sulfur oxide/, and /chlorine/.

计算性质

  • 辛醇/水分配系数(LogP):
    1.03
  • 重原子数:
    19
  • 可旋转键数:
    4
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.42
  • 拓扑面积:
    104
  • 氢给体数:
    3
  • 氢受体数:
    5

ADMET

代谢
在体内转化为硫胺素二磷酸,是α-酮酸脱羧的辅酶。
Converted in vivo to thiamine diphosphate, a coenzyme in the decarboxylation of alpha-keto acids.
来源:Hazardous Substances Data Bank (HSDB)
代谢
3-(2'-甲基-4'-氨基-5'-嘧啶甲基)-4-甲基噻唑-5-乙酸,即硫胺乙酸,2-甲基-4-氨基-5-甲酰氨基甲基嘧啶和5-(2-羟基乙基)-4-甲基噻唑已被确认为硫胺素(维生素B1)的重要代谢物。
Compound 3-(2'-methyl-4'-amino-5'-pyrimidylmethyl)-4-methylthiazole-5-acetic acid, ie thiamine acetic acid, 2-methyl-4-amino-5-formylaminomethylpyrimidine, and 5-(2-hydroxyethyl)-4-methylthiazole have been identified as important metabolites of thiamine, vitamin B1.
来源:Hazardous Substances Data Bank (HSDB)
代谢
生物转化哺乳动物中的硫胺素通常被认为会产生硫色素、硫胺素二硫化物、5-(2-羟基乙基)-4-甲基噻唑,以及一些与硫胺素嘧啶残基相对应的形式。
Biotransformation of thiamine in mammals is generally supposed to /yield/ thiochrome, thiamine disulfide, 5-(2-hydroxyethyl)-4-methyl-thiazole, and some form corresponding to pyrimidine residue of thiamine.
来源:Hazardous Substances Data Bank (HSDB)
代谢
维生素B1在动物肝脏中被代谢。在人体中已经鉴定出几种维生素B1的尿液代谢物。在给予生理剂量后,尿液中几乎没有或没有未改变的维生素B1排出;然而,在给予较大剂量后,当组织储存饱和时,未改变的维生素B1和代谢物都会被排出。
Thiamine is metabolized in the liver of animals. Several urinary metabolites of thiamine have been identified in humans. Little or no unchanged thiamine is excreted in urine following administration of physiologic doses; however, following administration of larger doses, both unchanged thiamine and metabolites are excreted after tissue stores become saturated.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
... 高剂量的盐酸硫胺素据报道会降低大鼠体内佐沙佐胺和氨基比林的代谢,而不会显著改变己巴比妥的氧化代谢。/盐酸硫胺素/
... High dietary levels of thiamine hydrochloride have been reported to depress the metabolism of zoxazolamine and aminopyrine in rats without significantly altering the oxidative metabolism of hexobarbitone. /Thiamine hydrochloride/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
在用PCB处理的大鼠中,血液、肝脏和坐骨神经中的维生素B1水平降低,转酮醇酶活性下降,而焦磷酸效应增加。在DDT处理的大鼠中,血液、大脑和肝脏中的维生素B1水平降低,转酮醇酶活性也下降,同时焦磷酸效应增加。
In rats treated with PCB, vitamin B1 levels in blood, liver, and sciatic nerve decreased, transketolase activity decreased, and pyrophosphate effect increased. In DDT-treated rats, vitamin B1 levels decreased in blood, brain, and liver, as did transketolase activity, while pyrophosphate effect increased.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
尽管其临床重要性尚不清楚,但据报道,硫胺素可能会增强神经肌肉阻滞剂的效果。
Although the clinical importance is unknown, thiamine reportedly may enhance the effect of neuromuscular blocking agents.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
... 酒精抑制了硫胺素的吸收。
... Alcohol inhibits absorption of thiamine.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 解毒与急救
/SRP:/ 立即急救:确保已经进行了充分的中和。如果患者停止呼吸,请开始人工呼吸,最好使用需求阀复苏器、球囊阀面罩设备或口袋面罩,按训练操作。如有必要,执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果患者呕吐,让患者向前倾或将其置于左侧(如果可能的话,头部向下)以保持呼吸道畅通,防止吸入。保持患者安静,维持正常体温。寻求医疗帮助。 /毒物A和B/
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
维生素B1的吸收主要发生在空肠。在维生素B1低浓度时,通过涉及磷酸化的主动运输系统进行吸收;在较高浓度时,通过被动扩散吸收。高剂量维生素B1只有一小部分被吸收,而且血中水平升高会导致维生素通过尿液主动排出。
Absorption of thiamin occurs mainly in the jejunum. At low concentrations of thiamin, absorption occurs by an active transport system that involves phosphyrylation; at higher concentrations, absorption occurs by passive diffusion. Only a small percentage of a high dose of thiamin is absorbed, and elevated serum values result in active urinary excretion of the vitamin.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
维生素B1在血液中通过红细胞和血浆进行传输,并通过尿液排出体外。
Thiamin is transported in blood in both erythrocytes and plasma and is excreted in the urine.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
维生素B1从小肠吸收并在肠粘膜中被磷酸化。
Thiamine is absorbed from the small intestine and is phosphorylated in the intestinal mucosa.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
维生素B很容易从小肠吸收,但在吸收不良综合症的情况下则不然。硫胺素主要在十二指肠吸收。
The B vitamins are readily absorbed from the gastrointestinal tract, except in malabsorption syndromes. Thiamine is absorbed mainly in the duodenum.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 安全说明:
    S22,S26,S36/37/39
  • 海关编码:
    3004500000
  • 危险性防范说明:
    P261,P305+P351+P338
  • 危险性描述:
    H302,H315,H319,H335

SDS

SDS:abe3e82d04664a4e5e7c9794ae22611c
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制备方法与用途

维生素B1简介

维生素B1亦称“硫胺”、“硫胺素”,是B族维生素之一。其能够促进正常的糖代谢,并且是维持神经传导、心脏和胃肠道正常功能所必需的物质。它与三磷酸腺苷结合形成维生素B1焦磷酸盐(二磷酸硫胺即辅酸酶),该辅酶在碳水化合物代谢过程中不可或缺,若缺乏则会导致氧化代谢受阻而形成丙酮酸及乳酸堆积,进而影响机体的能量供应。此外,维生素B1还能抑制胆碱酯酶的活性,当其不足时,会使乙酰胆碱水解加速,导致神经冲动传导障碍,并可能影响胃肠和心肌功能。

理化性质

维生素B1为白色细小结晶或晶粉状物质,熔点248℃(分解),极易溶于水且微溶于乙醇,而不溶于乙醚、苯已烷、氯仿等溶剂。其结构式如图1所示。

食物来源

维生素B1广泛存在于种子外皮及胚芽中,例如米糠、麦麸等粗粮中的含量高于精制米或白面粉;酵母、瘦肉、花生、黄豆、肝脏、全麦以及新鲜蔬果(如白菜、芹菜、菠菜、香蕉、橘子、葡萄)、中药防风、车前子、薏苡仁中均含有丰富的维生素B1。目前,药用的维生素B1为人工合成的硫胺盐酸盐。

生理功能与作用

维生素B1在糖代谢过程中起着辅酶的作用,是丙酮酸氧化脱羧所必需的物质。研究表明,I型糖尿病病人血清中维生素B1水平降低,而老年II型糖尿病病人血清维生素B1水平正常。因此,从维生素B1与糖代谢密切关系来看,其缺乏首先会引起糖代谢旺盛器官和组织的功能紊乱,如神经系统和心脏功能的混乱。临床上观察到,维生素B1对神经病变、尤其是痛性神经病变具有一定的疗效。

维生素B1可维持神经和心肌正常功能。有证据显示,患充血性心力衰竭者长期服用后,症状有所缓解。此外,它还能帮助消化不良及心肌炎的辅助治疗。对于烧伤、发热、长期慢性感染患者;吸收不良综合征伴肝胆系统疾病(如酒精中毒伴肝硬化)、小肠疾病(如乳糜泻、持续腹泻等)、胃切除术后、甲状腺功能亢进及进行血液透析的患者,以及长时间肠外营养或摄入不足导致的营养不良,维生素B1也具有补充作用。

缺乏症

维生素B1缺乏症称为脚气病。在成人中,分为湿性和干性两种类型,分别影响心血管系统和神经系统;婴幼儿则除上述症状外还可能累及消化系统,从而影响其生长发育。

副作用

维生素B1的毒性较低,副作用少见。少数人注射给药后可能出现过敏反应,表现为皮疹、痉挛、瘙痒、喘鸣甚至过敏性休克。长效制剂长期服用会出现头晕、乏力、焦躁等现象,停药后可消失。

合成方法

合成维生素B1的方法多样,可以通过米糠发酵或化学合成法获得。

测定方法

测定维生素B1含量的方法有荧光法、分光光度法、化学方法、电化学法和薄层色谱法等。

注意事项
  • 不宜静注,因可能引起过敏性休克甚至死亡。
  • 肌注时应深部注射并更换注射部位,必要时做皮内过敏试验。
  • 大量用药可干扰血清茶碱浓度测定、尿酸浓度假性增高及尿胆原阳性。
用途

维生素B1适用于治疗维生素B1缺乏症,具有维持正常糖代谢及神经传导的功能;也用于消化不良、神经炎等疾病的辅助治疗。

生产方法

通常由过量的盐酸乙脒与α-二甲氧基β-甲氧基丙腈经缩合、水解、中和、氧化、酸化得硫胺盐酸盐。

反应信息

  • 作为反应物:
    描述:
    thiamin chloride hydrochloridesodium hydroxidesodium trimethoxyborohydride 作用下, 以 甲醇 为溶剂, 以60.1%的产率得到5-[[(3aR,6aS)-3a-methyl-2,5,6,6a-tetrahydrofuro[2,3-d][1,3]thiazol-3-yl]methyl]-2-methylpyrimidin-4-amine
    参考文献:
    名称:
    The Correct Structures of “Dihydrothiamine”. Resolution of a Long-Standing Controversy
    摘要:
    Reduction of thiamin (1) by a borohydride in water first gives bicyclic perhydrofuro[2,3-d]thiazole 3, Heating 3 in water generates fused tricyclic pyrimido[4,5-d]thiazolo[3,4-a]pyrimidine 4. X-ray crystal structures indicate the stereocenters are cis in 3 and cis-cis in 4, The kinetics of reduction of both 3 and 4 to tetrahydrothiamin 5 by additional aqueous borohydride show that 3 is the kinetic product of the reduction of 1 while 4 is the thermodynamic product produced from 3 in an acid-catalyzed ring-opening ring-closing isomerization process. Several structural assignments of ''dihydrothiamine'' presented some 40 years ago are incorrect, Subsequent reports based on the incorrect structures need to be reinterpreted.
    DOI:
    10.1021/jo970782n
  • 作为产物:
    描述:
    果糖 、 alkaline earth salt of/the/ methylsulfuric acid 以 为溶剂, 生成 thiamin chloride hydrochloride
    参考文献:
    名称:
    Thiamin biosynthesis in Saccharomyces cerevisiae: origin of the pyrimidine unit
    摘要:
    DOI:
    10.1021/ja00261a024
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文献信息

  • Novel use of flavones
    申请人:——
    公开号:US20010046963A1
    公开(公告)日:2001-11-29
    A pharmaceutical composition for inhibiting COX- 2 biosynthesis comprising a therapeutically effective amount of the compound of formula I and a pharmaceutrically acceptable carrier. 1 wherein R 1 and R 4 represent either Hydrogen or together a bond R 5 , R 6 , R 7 , R 8 represent independently of each other Hydrogen, Hydroxy or Methoxy; in addition R 7 represents a sugar substituent like glucoside, rutinosid, manno gluco pyransyl, aprosylglucoside R 2 and R 3 represent Hydrogen, Hydroxy, Methoxy or 2 wherein R 2 ′, R 3 ′, R 4 ′, R 5 ′ and R 6 ′ are independently or each other Hydrogen, Hydroxy or Methoxy with the proviso, that R 2 or R 3 is represented by the optionally substituted Phenylring.
    一种用于抑制COX-2生物合成的药物组合物,包括化合物I的治疗有效量和药用可接受的载体。 其中R1和R4代表氢或一起表示键 R5、R6、R7、R8分别独立地表示氢、羟基或甲氧基;此外,R7表示糖取代物,如葡萄糖苷、鲁丁苷、甘露葡糖吡喃基、阿普罗西糖苷 R2和R3表示氢、羟基、甲氧基或 其中R2'、R3'、R4'、R5'和R6' 分别或彼此独立地表示氢、羟基或甲氧基,条件是R2或R3由可选择取代的苯环表示。
  • The Need for an Alternative to Radicals as the Cause of Fragmentation of a Thiamin-Derived Breslow Intermediate
    作者:Michael Bielecki、Ronald Kluger
    DOI:10.1002/anie.201702240
    日期:2017.5.22
    (1) is a conjugate of benzoylformate and thiamin that loses CO2 to form the classic Breslow intermediate (2), whose expected fate is formation of the thiamin conjugate of benzaldehyde (3). Surprisingly, it was observed that 2 decomposes to 4 and 5 and rearranges to 6 in competition with the expected protonation to give 3. Recent reports propose that the alternatives to protonation arise from homolysis
    曼荼罗硫胺素(1)是苯甲酰甲酸酯和硫胺素的共轭物,会损失CO 2形成经典的Breslow中间体(2),其预期结果是形成苯甲醛的硫胺素共轭物(3)。出乎意料的是,观察到2与预期的质子化竞争而分解为4和5,并重排为6,从而得到3。最近的报告提出质子化的替代方法来自均质化,然后是自由基为中心的过程。现在发现,为支持所提出的自由基途径而引用的光谱观察结果很可能是其他事件的结果。另一种解释是2的烯醇羟基的电离和产生的电子重组会导致CC键断裂和易于形成4、5和6的非自由基中间体。
  • METHOD OF MANUFACTURING SUCCINIC ACID AND AMMONIUM SUCCINATE SOLUTIONS
    申请人:Nishi Kiyohiko
    公开号:US20100094051A1
    公开(公告)日:2010-04-15
    The present invention provides a method of manufacturing a highly pure ammonium succinate solution including the steps of (A) producing calcium succinate trihydrate by crystallization fermentation of a microorganism; (B) converting calcium succinate trihydrate to calcium succinate monohydrate by transition crystallization; (C) separating the calcium succinate monohydrate crystals; (D) substituting the calcium salt in the calcium succinate monohydrate with ammonium salt resulting in an ammonium succinate solution; and (E) removing the solid calcium carbonate from the ammonium succinate solution.
    本发明提供了一种制备高纯度丙二酸铵溶液的方法,包括以下步骤:(A)通过微生物结晶发酵生产出苹果酸钙三水合物;(B)将苹果酸钙三水合物转化为苹果酸钙单水合物;(C)分离苹果酸钙单水合物晶体;(D)用铵盐替代苹果酸钙单水合物中的钙盐,得到丙二酸铵溶液;(E)从丙二酸铵溶液中去除固体碳酸钙。
  • Method for purifying succinic acid from fermentation broth
    申请人:Kushiku Takeshi
    公开号:US20060276674A1
    公开(公告)日:2006-12-07
    Succinic acid is produced by bringing a succinic acid-containing liquid containing succinic acid and cation which is obtained by fermentation or an enzymatic method into contact with an H-type strongly acidic cation-exchange resin in an amount equivalent to or more than the amount of cation other than hydrogen ion contained in the succinic acid-containing liquid, and precipitating a crystal of succinic acid from the obtained ion-exchange-treated liquid to obtain purified succinic acid.
    琥珀酸是通过将含有琥珀酸和阳离子的琥珀酸液体与通过发酵或酶法获得的H型强酸性阳离子交换树脂接触,接触量等于或超过琥珀酸液体中除氢离子外的阳离子量,并从获得的离子交换处理液体中沉淀出琥珀酸晶体以获得纯化的琥珀酸来生产的。
  • TRANSGENIC PLANT HAVING HERBICIDE RESISTANCE
    申请人:KUMIAI CHEMICAL INDUSTRY CO., LTD.
    公开号:US20190263874A1
    公开(公告)日:2019-08-29
    The invention is intended to identify glutathione-S-transferase that exhibits the activities to metabolize and detoxify an isoxazoline derivative, such as pyroxasulfone. The invention provides a method for cultivating a transgenic plant into which a nucleic acid encoding a protein (a or b) below has been introduced in the presence of isoxazoline derivatives: (a) a protein comprising the amino acid sequence as shown in SEQ ID NO: 2; or (b) a protein comprising an amino acid sequence having 80% or higher identity to the amino acid sequence as shown in SEQ ID NO: 2 and having the activity of glutathione-S-transferase.
    本发明旨在鉴定具有代谢和解毒异噁唑啉衍生物(例如吡草磺隆)活性的谷胱甘肽-S-转移酶。本发明提供了一种方法,通过引入编码下列蛋白质(a或b)的核酸到转基因植物中,在异噁唑啉衍生物存在的情况下培养转基因植物:(a) 包含如SEQ ID NO: 2所示的氨基酸序列的蛋白质;或(b) 包含与如SEQ ID NO: 2所示的氨基酸序列具有80%或更高同源性并具有谷胱甘肽-S-转移酶活性的氨基酸序列的蛋白质。
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