riboflavin tetrabutyrate | 752-56-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: riboflavin tetrabutyrate
• 英文别名: 7,8-dimethyl-10-(tetrakis-O-butyryl-pentitol-1-yl)-10H-benzo[g]pteridine-2,4-dione；riboflavin, 2',3',4',5'-tetrabutanoate；Vitamin B2-Tetrabutyrat；Riboflavintetrabutyrat；Hibon；[2,3,4-tri(butanoyloxy)-5-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)pentyl] butanoate
• CAS: 752-56-7
• 化学式: C₃₃H₄₄N₄O₁₀
• 分子量: 656.733
• InChiKey: MJNIWUJSIGSWKK-UHFFFAOYSA-N

物化性质

• 熔点：
  149 °C
• 密度：
  1.250 g/cm3
• 溶解度：
  可溶于DMSO（少量）、甲醇（少量）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  47
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  11

安全信息

• 安全说明：
  S22,S24/25
• 危险性防范说明：
  P233,P260,P261,P264,P271,P280,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Riboflavin Tetrabutyrate Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: Riboflavin Tetrabutyrate

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols None
No signal word
Signal word
Hazard statements None
None
Precautionary statements:

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: Riboflavin Tetrabutyrate
Percent: >98.0%(LC)
CAS Number: 752-56-7
Synonyms: Vitamin B2 Tetrabutyrate
Chemical Formula: C33H44N4O10

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Riboflavin Tetrabutyrate

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Section 5. FIRE-FIGHTING MEASURES
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
Colour: Reddish yellow - Yellow red
Odour: No data available
pH: No data available
Melting point/freezing point:149°C
No data available
Boiling point/range:
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
No data available
Relative density:
Solubility(ies):
Very slightly soluble
[Water]
[Other solvents]
Ethanol
Soluble:
Slightly soluble: Ether
Riboflavin Tetrabutyrate

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: ipr-rat LD50:>4500 mg/kg
orl-rat LD50:>7500 mg/kg
Skin corrosion/irritation: No data available
No data available
Serious eye
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
No data available
IARC =
NTP = No data available
No data available
Reproductive toxicity:
RTECS Number: VJ1755000

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
Riboflavin Tetrabutyrate

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

鉴别试验

取试样1mg，溶于100ml乙醇中，应呈浅黄绿色，并发出带黄绿色强荧光。再加入稀盐酸(TS-117)或氢氧化钠试液(TS-224)时，荧光消失。

另取试样10mg溶解在5ml乙醇中，加由15%盐酸羟胺溶液和15%氢氧化钠溶液等体积混合液2ml，充分摇匀后，再依次加入O．8ml盐酸、O．5ml氯化铁试液(TS-101)及等体积的乙醇。溶液应呈现深红棕色。

含量分析

将试样在真空干燥器（硫酸）中干燥4小时后，精确称取约40mg，在乙醇中溶解并稀释至500ml。取其中10ml，用乙醇定容至50ml，作为试样液。将该溶液置于1cm比色池中，并在波长445nm处测定吸光度A1，以乙醇为空白对照。

另称取标准核黄素约50mg，在105℃下干燥3小时后溶解于含冰醋酸4ml和水150ml的混合液中。加热溶解冷却后，再加水定容至500ml，从中取5ml，用乙醇定容至50ml作为标准液。

同样地，在波长445nm处测定标准液的吸光度A2，并按以下公式求得核黄素四丁酸酯(C33H44O10N4)的含量：

$$ \text{含量(％)} = \left(\frac{A_1}{A_2}\right) \times \left[\frac{25 \times 1.745}{\text{式样量（mg）}}\right] \times 100 $$

毒性

毒性极低，LD50＞15g/kg(小鼠，经口)。大鼠按500～2000mg/kg给予6个月，未见明显变化。

使用限量

GB 14880—94：同“01022，核黄素”。

生物活性

核黄素四丁酸酯是一种亲脂性黄素衍生物，具有抗氧化作用和去除脂类过氧化物的活性。

体外研究

核黄素四丁酸酯可抑制由自由基介导的脂质过氧化。它能抑制NADPH耦合及抗坏血酸诱导的微小胞质中脂质过氧化反应，表明其抗氧化作用可能在酶促氧化还原反应过程中从多不饱和脂肪酸的活性甲基上摘取氢原子之后才开始显现。

体内研究

核黄素四丁酸酯能通过抑制脂质过氧化来改善血脂代谢，从而减少血液中升高的胆固醇。喂食核黄素四丁酸酯可使肝3-酮酰基辅酶A硫解酶活性提高50%，而肾3-酮酰基辅酶A硫解酶及肝、肾中的酰基辅酶A合成酶和脱氢酶的活性未受影响。肝脏中3-酮酰基辅酶A硫解酶活性增加表明长期喂食核黄素四丁酸酯可导致肝脏中脂肪酸β氧化增加。

反应信息

• 作为试剂：
  描述：

  (3R,4R)-4-ethenyl-3-prop-2-enyloxolan-2-ol 在 吡啶 、 Grubbs catalyst first generation 、 叔丁基过氧化氢 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 vanadyl acetylacetonate 、 2-甲基-6-硝基苯甲酸酐 、 potassium tert-butylate 、 四丁基氟化铵 、 氧气 、 titanium(IV)isopropoxide 、 二异丁基氢化铝 、 碳酸氢钠 、 potassium carbonate 、 D-(-)-酒石酸二异丙酯 、 magnesium 、 溶剂黄146 、 二甲基亚砜 、 riboflavin tetrabutyrate 、 三乙胺 、 sodium iodide 、 lithium hydroxide 、 lithium hexamethyldisilazane 、 肼 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 200.41h， 生成 (-)-hybridalactone
  参考文献：
  名称：

  海洋类二十烷酸（-）-Hybridalactone的全合成

  摘要：

  （−）‐ Hybridalactone（1）是从红藻Laurencia hybrida中分离出来的海洋类二十烷酸。这种天然产物包含环丙烷，环戊烷，13元大环内酯和环氧化物环系统，其中包含七个立体异构中心。此外，该化合物具有酸不稳定的Z，Z-二烯基。在本文中，我们报道了（-）-hybridalactone（1）的总合成。从旋光性γ-丁内酯2开始，以线性顺序（包括21个步骤）合成了独特的类二十烷酸（-）-乙内酯（1），总收率为21.9％。（-）-hybridalactone（1的合成中的关键步骤）是由苯磺酰乙酸甲酯介导的顺-环丙烷-γ-内酯衍生物的一锅合成。该反应提供了对顺式-环丙烷-γ-内酯12的高效和立体选择。通过脱磺酰化，环氧化，氧化，Wittig烯化和椎名椎间孔大内酯化进一步修饰后一种化合物，可得到（-）-杂交内酯。

  DOI：

  10.1002/chem.201200210

文献信息

• ANTI-AGING AGENT CONTAINING ARCTIGENIN DERIVATIVE
  申请人：ROHTO Pharmaceutical Co., Ltd.

  公开号：US20150093345A1

  公开（公告）日：2015-04-02

  An arctigenin derivative used for anti-aging treatment, including protection of the skin from the sun and recovery of skin elasticity. A variety of fatty acid ester derivatives, alcohol ether derivatives and alkylated derivatives are used as the arctigenin derivatives. Agents for controlling ET-1 production, elastase inhibitors, and anti-inflammatory agents are prepared. Such arctigenin derivatives are particularly useful as an external agent for the skin, such as an anti-inflammatory external agent, a sunscreen external agent, or an external agent for recovering elasticity.

  一种用于抗衰老治疗的牛蒡素衍生物，包括保护皮肤免受阳光伤害和恢复皮肤弹性。使用各种脂肪酸酯衍生物、醇醚衍生物和烷基衍生物作为牛蒡素衍生物。制备用于控制ET-1产生的药剂、弹性蛋白酶抑制剂和抗炎药剂。这种牛蒡素衍生物特别适用于皮肤外用剂，如抗炎外用剂、防晒外用剂或恢复弹性的外用剂。
• VITAMIN COMPRISING PYROLOQUINOLINE QUINONE AND USE THEREOF
  申请人：RIKEN

  公开号：EP1588709A1

  公开（公告）日：2005-10-26

  It is an object of the present invention to clarify the biochemical role of pyrroloquinoline quinone (PQQ) in living bodies by identifying an enzyme that uses PQQ as a coenzyme in mammals and then by clarifying the oxidation-reduction reaction, with which PQQ is associated as a coenzyme in living bodies. The present invention provides a method of using pyrroloquinoline quinone as a coenzyme for 2-aminoadipate 6-semialdehyde dehydrogenase.

  本发明的目的是通过鉴定在哺乳动物中使用吡咯喹啉喹醌（PQQ）作为辅酶的酶，然后通过澄清PQQ作为辅酶与氧化还原反应相关联的方式，来澄清PQQ在生物体内的生化作用。本发明提供了一种利用吡咯喹啉喹醌作为2-氨基己二酸6-半醛脱氢酶的辅酶的方法。
• [EN] DECARBOXYLATIVE CONJUGATE ADDITIONS AND APPLICATIONS THEREOF<br/>[FR] ADDITIONS DE CONJUGUÉS AVEC DÉCARBOXYLATION ET APPLICATIONS ASSOCIÉES
  申请人：UNIV PRINCETON

  公开号：WO2016196931A1

  公开（公告）日：2016-12-08

  Synthetic methods are described herein operable to efficiently produce a wide variety of molecular species through conjugate additions via decarboxylative mechanisms. For example, methods of functionalization of peptide residues are described, including selective functionalization of peptide C-terminal residues. In one aspect, a method of peptide functionalization comprises providing a reaction mixture including a Michael acceptor and a peptide and coupling the Michael acceptor with the peptide via a mechanism including decarboxylation of a peptide reside.

  本文描述了可操作的合成方法，能够通过脱羧机制通过共轭加成有效地产生各种分子物种。例如，描述了肽残基的官能化方法，包括对肽C-末端残基的选择性官能化。在一个方面，肽官能化方法包括提供包括迈克尔受体和肽的反应混合物，并通过包括肽残基的脱羧机制将迈克尔受体与肽偶联。
• Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases
  申请人：Scaramuzzino, Giovanni

  公开号：EP1336602A1

  公开（公告）日：2003-08-20

  New pharmaceutical compounds of general formula (I): F-(X)q where q is an integer from 1 to 5, preferably 1; -F is chosen among drugs described in the text, -X is chosen among 4 groups -M, -T, -V and -Y as described in the text. The compounds of general formula (I) are nitrate prodrugs which can release nitric oxide in vivo in a controlled and selective way and without hypotensive side effects and for this reason they are useful for the preparation of medicines for prevention and treatment of inflammatory, ischemic, degenerative and proliferative diseases of musculoskeletal, tegumental, respiratory, gastrointestinal, genito-urinary and central nervous systems.

  通式（I）的新药物化合物：F-（X）q，其中q是1到5的整数，最好是1；-F是在文本中描述的药物中选择的，-X是在文本中描述的4个组-M，-T，-V和-Y中选择的。通式（I）的化合物是硝酸盐前药，可以在体内以受控和选择性的方式释放一氧化氮，而不会产生降压副作用，因此它们非常适用于制备用于预防和治疗肌肉骨骼，皮肤，呼吸，消化，泌尿和中枢神经系统的炎症，缺血，退行性和增生性疾病的药物。
• PHARMACEUTICAL FORMULATION CONTAINING ANGIOTENSIN-II RECEPTOR BLOCKER
  申请人：Kim Sung Wuk

  公开号：US20110117194A1

  公开（公告）日：2011-05-19

  The present invention provides a pharmaceutical formulation containing an angiotensin-II receptor blocker and a release-control material as a pharmacologically active ingredient and a pharmaceutical formulation comprising an immediate-release compartment and an extended-release compartment. The immediate-release compartment contains an agent as a pharmacologically active ingredient for preventing and inhibiting hepatitis and the extended-release compartment has an angiotensin-II receptor blocker as a pharmacologically active ingredient. The formulation of the present invention maximizes the effectiveness on pharmacologically and clinically lowering blood pressure and preventing complications when taking the formulation, helps to avoid interaction with a drug which is metabolized by the same enzyme in the liver, and prevents and inhibits the incidence of drug-induced hepatitis which is caused by drug administration for a long time.

  本发明提供一种药物制剂，其包含一种血管紧张素II受体拮抗剂和一种释放控制材料作为药理活性成分，以及一种包括即时释放隔间和延时释放隔间的药物制剂。即时释放隔间含有一种药理活性成分，用于预防和抑制肝炎，而延时释放隔间则含有一种血管紧张素II受体拮抗剂作为药理活性成分。本发明的制剂在服用时最大程度地提高了药理和临床降低血压、预防并发症的有效性，有助于避免与同样在肝脏中代谢的药物发生相互作用，并预防和抑制由于长期用药引起的药物性肝炎的发生。