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riboflavin | 301335-02-4

中文名称
——
中文别名
——
英文名称
riboflavin
英文别名
vitamin B2;7,8-dimethyl-10-[(2R,3R,4S)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione;7,8-dimethyl-10-(2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4-dione
riboflavin化学式
CAS
301335-02-4
化学式
C17H20N4O6
mdl
MFCD00066861
分子量
376.369
InChiKey
AUNGANRZJHBGPY-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

计算性质

  • 辛醇/水分配系数(LogP):
    -1.5
  • 重原子数:
    27
  • 可旋转键数:
    5
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.41
  • 拓扑面积:
    155
  • 氢给体数:
    5
  • 氢受体数:
    7

ADMET

代谢
自由核黄素在小肠粘膜中被转化为单核苷酸黄素,后者在肝脏中转变为黄素腺嘌呤二核苷酸。
Free riboflavin is converted in the intestinal mucosa into flavin mononucleotide which is transformed into flavin adenine dinucleotide in the liver.
来源:Hazardous Substances Data Bank (HSDB)
代谢
核黄素的代谢是一个受到严格调控的过程,它依赖于个体的核黄素状态。核黄素在大多数组织细胞的细胞质中被转化为辅酶,但主要在小肠、肝脏、心脏和肾脏中转化。核黄素的代谢过程始于腺苷三磷酸(ATP)依赖性的磷酸化,将维生素转化为黄素单核苷酸(FMN)。催化这一转化的黄素激酶受到激素的控制。FMN然后可以与特定的apo酶结合,形成各种黄素蛋白;然而,大部分通过FAD合成酶转化为黄素腺嘌呤二核苷酸(FAD)。因此,FAD是身体组织中主要的黄素辅酶。FAD的产生受到产物抑制的调控,即过量的FAD会抑制其进一步的产生。
The metabolism of riboflavin is a tightly controlled process that depends on the riboflavin status of the individual. Riboflavin is converted to coenzymes within the cellular cytoplasm of most tissues but mainly in the small intestine, liver, heart, and kidney. The metabolism of riboflavin begins with the adenosine triphosphate (ATP)-dependent phosphorylation of the vitamin to flavin mononucleotide (FMN). Flavokinase, the catalyst for this conversion, is under hormonal control. FMN can then be complexed with specific apoenzymes to form a variety of flavoproteins; however, most is converted to flavin-adenine dinucleotide (FAD) by FAD synthetase. As a result, FAD is the predominant flavocoenzyme in body tissues. Production of FAD is controlled by product inhibition such that an excess of FAD inhibits its further production.
来源:Hazardous Substances Data Bank (HSDB)
代谢
一个核黄素分子的生物合成需要一分子GTP和两分子核酮糖5-磷酸作为底物。GTP通过一序列的脱氨、侧链还原和去磷酸化反应水解释放,转化为5-氨基-6-核糖基氨基-2,4(1H,3H)-嘧啶二酮。与从核酮糖5-磷酸获得的3,4-二羟基-2-丁酮4-磷酸的缩合导致6,7-二甲基-8-核糖基乳清酸。维生素生物合成的最后一步涉及6,7-二甲基-8-核糖基乳清酸的歧化,该反应由核黄素合成酶催化。这个在机制上不寻常的反应涉及两个相同底物分子之间四碳片段的转移。第二个产物,5-氨基-6-核糖基氨基-2,4(1H,3H)-嘧啶二酮,通过6,7-二甲基-8-核糖基乳清酸合酶在生物合成途径中回收。本文将回顾到2007年的核黄素合成酶和相关蛋白的结构和反应机制,并引用了122篇参考文献。
The biosynthesis of one riboflavin molecule requires one molecule of GTP and two molecules of ribulose 5-phosphate as substrates. GTP is hydrolytically opened, converted into 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione by a sequence of deamination, side chain reduction and dephosphorylation. Condensation with 3,4-dihydroxy-2-butanone 4-phosphate obtained from ribulose 5-phosphate leads to 6,7-dimethyl-8-ribityllumazine. The final step in the biosynthesis of the vitamin involves the dismutation of 6,7-dimethyl-8-ribityllumazine catalyzed by riboflavin synthase. The mechanistically unusual reaction involves the transfer of a four-carbon fragment between two identical substrate molecules. The second product, 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione, is recycled in the biosynthetic pathway by 6,7-dimethyl-8-ribityllumazine synthase. This article will review structures and reaction mechanisms of riboflavin synthases and related proteins up to 2007 and 122 references are cited.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 暴露途径
该物质可以通过摄入被身体吸收。
The substance can be absorbed into the body by ingestion.
来源:ILO-WHO International Chemical Safety Cards (ICSCs)
毒理性
  • 吸入症状
咳嗽。喉咙痛。
Cough. Sore throat.
来源:ILO-WHO International Chemical Safety Cards (ICSCs)
毒理性
  • 眼睛症状
红斑。疼痛。
Redness. Pain.
来源:ILO-WHO International Chemical Safety Cards (ICSCs)
毒理性
  • 相互作用
核黄素与其他B族维生素,尤其是烟酸和维生素B6相互关联。烟酸需要核黄素才能从色氨酸中形成,而维生素B6也需要核黄素来转化为辅酶形式。这些相互关系目前认为不会影响对核黄素的需求。
Riboflavin interrelates with other B vitamins, notably niacin, which requires riboflavin for its formation from tryptophan, and vitamin B6, which also requires riboflavin for a conversion to a conenzyme form. These interrelationships are not known to affect the requirement for riboflavin.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
据报道,普鲁本辛溴盐影响核黄素的吸收速率和程度。预先给予普鲁本辛溴盐会延迟核黄素的吸收速率,但增加了总共吸收的量,可能是通过增加了核黄素在消化道吸收位点的停留时间。
The rate and extent of absorption of riboflavin are reportedly affected by propantheline bromide. Prior administration of propantheline bromide delayed the rate of absorption of riboflavin but increased the total amount absorbed, presumably by increasing the residence time of riboflavin at GI absorption sites.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
核黄素从上消化道很容易被吸收;然而,药物的吸收涉及主动转运机制,且消化道吸收的量受到药物与吸收发生的特定粘膜部位接触时间的限制。在吸收发生之前,核黄素5'-磷酸在消化道腔内迅速且几乎完全去磷酸化。当与食物一起服用时,核黄素的消化道吸收量增加,而在肝炎、肝硬化、胆道阻塞的患者或接受丙磺舒治疗的患者中,吸收量减少。
Riboflavin is readily absorbed from the upper GI tract; however, absorption of the drug involves active transport mechanisms and the extent of GI absorption is limited by the duration of contact of the drug with the specialized segment of mucosa where absorption occurs. Riboflavin 5-phosphate is rapidly and almost completely dephosphorylated in the GI lumen before absorption occurs. The extent of GI absorption of riboflavin is increased when the drug is administered with food and is decreased in patients with hepatitis, cirrhosis, biliary obstruction, or in those receiving probenecid.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
核黄素在小肠通过一个快速、可饱和的传输系统被主要吸收。一小部分在大肠被吸收。吸收速率与摄入量成正比,并且当核黄素与食物一起摄入并在胆盐的存在下时,吸收速率会增加。在低摄入水平时,核黄素的大部分通过主动或促进运输系统被吸收。在较高的摄入水平时,核黄素可以通过被动扩散被吸收。
Primary absorption of riboflavin occurs in the small intestine via a rapid, saturable transport system. A small amount is absorbed in the large intestine. The rate of absorption is proportional to intake, and it increases when riboflavin is ingested along with other foods and in the presence of bile salts. At low intake levels, most absorption of riboflavin occurs via an active or facilitated transport system. At higher levels of intake, riboflavin can be absorbed by passive diffusion.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
在血浆中,大量的核黄素与其它蛋白质结合,主要是免疫球蛋白,用于运输。妊娠增加了可用于核黄素的载体蛋白的水平,这导致在胎盘的母体表面核黄素的吸收率更高。
In the plasma, a large portion of riboflavin associates with other proteins, mainly immunoglobulins, for transport. Pregnancy increases the level of carrier proteins available for riboflavin, which results in a higher rate of riboflavin uptake at the maternal surface of the placenta.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
在胃中,胃酸化作用会从蛋白质中释放出大多数核黄素(维生素B2)的辅酶形式(黄素腺嘌呤二核苷酸(FAD)和黄素单核苷酸(FMN))。随后,非共价结合的辅酶在上消化道被非特异性焦磷酸酶和磷酸酶水解成核黄素。核黄素的主要吸收发生在近端小肠,通过一个快速、可饱和的传输系统。吸收速率与摄入量成正比,当核黄素与食物一起摄入并存在胆盐时,吸收速率会增加。少量的核黄素通过肠肝循环系统循环。在低摄入水平时,核黄素的大部分吸收是通过主动或促进运输系统完成的。
In the stomach, gastric acidification releases most of the coenzyme forms of riboflavin (flavin-adenine dinucleotide (FAD) and flavin mononucleotide (FMN)) from the protein. The noncovalently bound coenzymes are then hydrolyzed to riboflavin by nonspecific pyrophosphatases and phosphatases in the upper gut. Primary absorption of riboflavin occurs in the proximal small intestine via a rapid, saturable transport system. The rate of absorption is proportional to intake, and it increases when riboflavin is ingested along with other foods and in the presence of bile salts. A small amount of riboflavin circulates via the enterohepatic system. At low intake levels most absorption of riboflavin is via an active or facilitated transport system.
来源:Hazardous Substances Data Bank (HSDB)

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    riboflavinsodium periodate 作用下, 以 为溶剂, 反应 2.0h, 生成 10-(2,2-dihydroxylethyl)-7,8-dimethylisoalloxazine
    参考文献:
    名称:
    放射性核素标记的苯并蝶啶类衍生物及其制 备方法和应用
    摘要:
    本发明公开了放射性核素标记的苯并蝶啶类衍生物及其制备方法和应用,其分子结构式如下:本发明具有在发生脑卒中后立即给药并在给药后5min即进行显像诊断就能清晰地看到病灶部位,这极大缩短了诊断时间,在脑卒中的黄金抢救时间内进行正确诊断,能够及时指导有效治疗,达到治疗效果最好和风险最低,这对患者病情预后有着至关重要的作用。
    公开号:
    CN108676007B
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文献信息

  • Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium
    作者:Michael Dobmeier、Josef M Herrmann、Dieter Lenoir、Burkhard König
    DOI:10.3762/bjoc.8.36
    日期:——
    was improved to be more applicable to organic synthesis. Instead of a strongly acidic, aqueous solution, a biphasic toluene-water reaction medium was used, which allowed the conversion of primary, secondary and tertiary benzylic alcohols, in good yields and short reaction times, into the corresponding hydrocarbons. Red phosphorous was used as the stoichiometric reducing agent. Keto, ester, amide or
    Kiliani 在 140 多年前首次描述的使用氢碘酸将醇还原为烃的合成方案经过改进,使其更适用于有机合成。使用双相甲苯-水反应介质代替强酸性水溶液,这使得伯、仲和叔苄醇以良好的产率和较短的反应时间转化为相应的烃。红磷用作化学计量还原剂。酮基、酯基、酰胺基或醚基是可以耐受的,并且在 0.6 当量磷存在下催化量的氢碘酸(0.2 当量)足以实现转化。
  • BORATE-BASED BASE GENERATOR, AND BASE-REACTIVE COMPOSITION COMPRISING SUCH BASE GENERATOR
    申请人:WAKO PURE CHEMICAL INDUSTRIES, LTD.
    公开号:US20160340374A1
    公开(公告)日:2016-11-24
    An object of the present invention is to provide a compound which is capable of attaining a composition having high storage stability without reacting with a base-reactive compound, even in the case of storage for a long period of time in a mixed state with the base-reactive compound, such as an epoxy-based compound, as well as capable of generating a strong base (guanidines, biguanides, phosphazenes or phosphoniums) by irradiation of light (active energy rays) or heating; a base generator comprising the compound; and a base-reactive composition comprising the base generator and the base-reactive compound. The present invention relates to the compound represented by the general formula (A); the base generator comprising the compound; and the base-reactive composition comprising the base generator and the base-reactive compound. (wherein R 1 represents an alkyl group; an arylalkynyl group which may be substituted with a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group; an alkenyl group; a 2-furylethynyl group; a 2-thiophenylethynyl group; or a 2,6-dithianyl group; R 2 to R 4 each independently represent an alkyl group; an arylalkynyl group which may be substituted with a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group; the aryl group which may be substituted with a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group; a furanyl group; a thienyl group; or an N-alkyl-substituted pyrrolyl group; Z + represents an ammonium cation having a guanidinium group, a biguanidium group or a phosphazenium group, or a phosphonium cation.)
    本发明的目的是提供一种化合物,能够在与碱反应性化合物混合状态长时间存储的情况下,仍能获得具有高储存稳定性的组合物,而不与碱反应性化合物发生反应,同时还能通过光照(活性能量射线)或加热产生强碱(胍胺、双胍胺、磷氮烷或磷銨);包括该化合物的碱发生器;以及包括该碱发生器和碱反应性化合物的碱反应性组合物。本发明涉及由通式(A)表示的化合物;包括该化合物的碱发生器;以及包括该碱发生器和碱反应性化合物的碱反应性组合物。(其中R1代表烷基;可能被卤素原子、烷基、烷氧基或烷硫基取代的芳基炔基;烯基;2-呋喃基炔基;2-噻吩基炔基;或2,6-二硫基基;R2到R4各自独立地代表烷基;可能被卤素原子、烷基、烷氧基或烷硫基取代的芳基炔基;可能被卤素原子、烷基、烷氧基或烷硫基取代的芳基;呋喃基;噻吩基;或N-烷基取代的吡咯基;Z+代表具有胍胺基团、双胍胺基团或磷氮烷基团的铵阳离子,或磷銨阳离子。)
  • 10H-BENZO[G]PTERIDINE-2,4-DIONE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, AND USE THEREOF
    申请人:Maisch Tim
    公开号:US20140200220A1
    公开(公告)日:2014-07-17
    The present disclosure relates to 10H-benzo[g]pteridine-2,4-dione derivatives, to the production thereof, and to the use thereof.
    本公开涉及10H-苯并[g]喹啉-2,4-二酮衍生物,其生产以及使用。
  • A new trick (hydroxyl radical generation) of an old vitamin (B<sub>2</sub>) for near-infrared-triggered photodynamic therapy
    作者:Fang Xu、Jin Li、Ting-ting Zhu、Sheng-Song Yu、Chong Zuo、Ri-sheng Yao、Hai-sheng Qian
    DOI:10.1039/c6ra23440b
    日期:——
    Photosensitizer has been supposed to the key component in photodynamic therapy (PDT). Natural products and their intricate molecular frameworks are often used as starting points for drug discovery. Riboflavin (RF),...
    光敏剂被认为是光动力疗法(PDT)的关键组成部分。天然产物及其复杂的分子框架通常被用作药物发现的起点。核黄素(RF),...
  • Novel Carboxylic Acid Derivatives
    申请人:Beumer Raphael
    公开号:US20090258887A1
    公开(公告)日:2009-10-15
    The present invention is concerned with novel arylalkyl carboxylic acid derivatives, more specifically, with acylates of arylalkyl carboxylic acids with naturally occurring, non-toxic hydroxy, sulfhydryl, amino or imino compounds, and to compositions containing them. The compositions are preferably cosmetic preparations.
    本发明涉及一种新颖的芳基烷基羧酸衍生物,更具体地说,涉及芳基烷基羧酸的酰化物与天然存在的、无毒的羟基、硫醇、氨基或亚氨基化合物的组合物,以及含有它们的组合物。这些组合物最好是化妆品制剂。
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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mass
cnmr
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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