5-羟甲基-2-呋喃甲酸 | 6338-41-6

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 5-羟甲基-2-呋喃甲酸
• 中文别名: 5-(羟基甲基)-2-糠酸；5-羟甲基呋喃甲酸；5-羟甲基-2-糠酸
• 英文名称: 5-hydroxymethyl-furan-2-carboxylic acid
• 英文别名: 5-hydroxymethylfuroic acid；5-hydroxymethyl-2-furancarboxylic acid；HMFCA；5-hydroxymethyl-2-furoic acid；sumiki's acid；5-(hydroxymethyl)furan-2-carboxylic acid
• CAS: 6338-41-6
• 化学式: C₆H₆O₄
• mdl: MFCD03274472
• 分子量: 142.111
• InChiKey: PCSKKIUURRTAEM-UHFFFAOYSA-N

物化性质

• 熔点：
  247°C (dec.)
• 沸点：
  349.4±32.0 °C(Predicted)
• 密度：
  1.441±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• LogP：
  -0.550 (est)
• 物理描述：
  Solid
• 稳定性/保质期：
  存在于烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2932190090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储条件为0-10°C，需置于惰性气体中，避免与空气接触并防止加热。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Hydroxymethyl-2-furancarboxylic acid
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 5-Hydroxymethyl-2-furancarboxylic acid
CAS number: 6338-41-6

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H6O4
Molecular weight: 142.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性：5-Hydroxymethyl-2-furancarboxylic acid（5-HMFA）是5-hydroxymethyl-2-furfural的主要代谢产物。5-hydroxymethyl-2-furfural是在食物加热和储存过程中酸催化的糖降解产物，不仅影响其口味，还可能在体内发挥生理作用。

靶点

Human Endogenous Metabolite

体外研究

5-Hydroxymethyl-2-furancarboxylic acid (HMFA) 可作为暴露于 HMFA 的生物标志物。

反应信息

• 作为反应物：
  描述：

  5-羟甲基-2-呋喃甲酸 在 盐酸 、 乙醚 、 氢溴酸 作用下， 生成 ethyl 5-(bromomethyl)furan-2-carboxylate
  参考文献：
  名称：

  183.蔗糖转化为呋喃化合物。第一部分。5-羟甲基糠醛及其衍生物

  摘要：

  DOI：

  10.1039/jr9440000667
• 作为产物：
  描述：

  5-(溴甲基)呋喃-2-甲醛 在 水 、 silver(l) oxide 作用下， 生成 5-羟甲基-2-呋喃甲酸
  参考文献：
  名称：

  Fenton; Gostling, Journal of the Chemical Society, 1899, vol. 75, p. 424

  摘要：

  DOI：

文献信息

• A biocatalytic method for the chemoselective aerobic oxidation of aldehydes to carboxylic acids
  作者：Tanja Knaus、Vasilis Tseliou、Luke D. Humphreys、Nigel S. Scrutton、Francesco G. Mutti

  DOI：10.1039/c8gc01381k

  日期：——

  optimised biocatalytic oxidation runs in phosphate buffer at pH 8.5 and at 40 °C. From a set of sixty-one aliphatic, aryl-aliphatic, benzylic, hetero-aromatic and bicyclic aldehydes, fifty were converted with elevated yield (up to >99%). The exceptions were a few ortho-substituted benzaldehydes, bicyclic heteroaromatic aldehydes and 2-phenylpropanal. In all cases, the expected carboxylic acid was shown

  在此，我们提出了一项使用三种重组醛脱氢酶（ALDH）将醛氧化为羧酸的研究。ALDH 以纯化形式与烟酰胺氧化酶 (NOx) 一起使用，该酶以双氧（大气压下的空气）为代价回收催化 NAD + 。为了更方便的实际应用，还使用冻干全细胞和静息细胞生物催化剂研究了该反应。优化的生物催化氧化在 pH 8.5 和 40 °C 的磷酸盐缓冲液中运行。从一组 61 种脂肪族、芳基脂肪族、苄基、杂芳族和双环醛中，其中 50 种以较高的产率转化（高达 >99%）。少数邻位取代的苯甲醛、双环杂芳醛和2-苯基丙醛除外。在所有情况下，预期的羧酸都是唯一的产物（>99% 化学选择性）。同一分子内的其他可氧化官能团（例如羟基、烯烃和杂芳族氮或硫原子）保持不变。该反应规模用于氧化 5-(羟甲基)糠醛 (2 g)（一种生物基原料），得到 5-(羟甲基)糠酸，分离收率为 61%。新的生物催化方法避免使用有毒或不安全的氧化剂、强
• Enzyme‐Catalyzed Oxidation of 5‐Hydroxymethylfurfural to Furan‐2,5‐dicarboxylic Acid
  作者：Willem P. Dijkman、Daphne E. Groothuis、Marco W. Fraaije

  DOI：10.1002/anie.201402904

  日期：2014.6.16

  Furan‐2,5‐dicarboxylic acid (FDCA) is a biobased platform chemical for the production of polymers. In the past few years, numerous multistep chemical routes have been reported on the synthesis of FDCA by oxidation of 5‐hydroxymethylfurfural (HMF). Recently we identified an FAD‐dependent enzyme which is active towards HMF and related compounds. This oxidase has the remarkable capability of oxidizing

  呋喃-2,5-二羧酸（FDCA）是用于生产聚合物的生物基平台化学品。在过去的几年中，已经报道了通过5-羟甲基糠醛（HMF）氧化合成FDCA的许多多步化学路线。最近，我们发现了一种对FAD依赖的酶，该酶对HMF和相关化合物具有活性。这种氧化酶具有将[5-（羟甲基）呋喃-2-基]甲醇氧化为FDCA的出色能力，该反应涉及四个连续的氧化反应。氧化酶可以在环境温度和压力下以高收率从HMF生产FDCA。对基本机理的研究表明，氧化酶仅作用于醇基，并且取决于形成FDCA所需的氧化反应中醛的水合反应。
• [EN] SMALL MOLECULE C-MYC INHIBITORS<br/>[FR] PETITES MOLÉCULES INHIBITRICES DE C-MYC
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2015089180A1

  公开（公告）日：2015-06-18

  This invention provides small molecule Myc-inhibitors. Also provided in the invention are therapeutic applications of these compounds for treating Myc-driven cancer and other related methods.

  这项发明提供了小分子Myc抑制剂。该发明还提供了这些化合物的治疗应用，用于治疗Myc驱动的癌症和其他相关方法。
• On the mechanism of selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over supported Pt and Au catalysts
  作者：Sara E. Davis、Bhushan N. Zope、Robert J. Davis

  DOI：10.1039/c1gc16074e

  日期：——

  The mechanism of selective oxidation of aqueous 5-hydroxymethylfurfural (HMF) at high pH was studied over supported Pt and Au catalysts. Results from labeling experiments conducted with 18O2 and H218O indicated that water was the source of oxygen atoms during the oxidation of HMF to 2-hydroxymethylfurancarboxylic acid (HFCA) and 2,5-furandicarboxylic acid (FDCA), presumably through direct participation

  选择性机制 氧化作用 水性 5-羟甲基糠醛 在负载的Pt和Au上研究了高pH下的HMF（HMF） 催化剂。结果来自贴标用18 O 2和H 2 18 O进行的实验表明水 是HMF氧化为的过程中氧原子的来源 2-羟甲基呋喃羧酸 （HFCA）和 2,5-呋喃二甲酸（FDCA），大概是由于氢氧化物直接参与了催化循环。分子氧对于FDCA的生产是必不可少的，并且在此过程中起了间接作用氧化作用通过去除沉积在负载金属颗粒中的电子。HMF的反应路径氧化作用 提出了对FDCA的建议。
• Cephalosporins and homologues, preparations and pharmaceutical
  申请人：——

  公开号：US06001997A1

  公开（公告）日：1999-12-14

  .beta.-Lactam antibiotics of formula (I) or a salt thereof, wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acyl group; CO.sub.2 R.sup.3 is a carboxy group or a carboxylate anion, or R.sup.3 is a readily removable carboxy protecting group; R.sup.4 represents up to four substituents; X is S, SO, SO.sub.2, O or CH.sub.2 ; m is 1 or 2; and n is 0, useful in the treatment of bacterial infections. ##STR1##

  (1)式β-内酰胺类抗生素或其盐，其中R1为氢、甲氧基或甲酰胺基；R2为酰基；CO2R3为羧基或羧酸根离子，或R3为易于去除的羧基保护基团；R4代表最多四个取代基；X为S、SO、SO2、O或CH2；m为1或2；n为0，用于治疗细菌感染。

表征谱图