别麦芽酚 | 644-46-2

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 别麦芽酚
• 中文别名: 异麦芽醇
• 英文名称: allomaltol
• 英文别名: 5-hydroxy-2-methyl-4H-pyran-4-one；2-methyl-5-hydroxypyran-4(1H)-one；5-hydroxy-2-methylpyran-4(1H)-one；6-methyl-3-hydroxypyran-4(1H)-one；3-Hydroxy-6-methyl-pyran-4(1H)-one；5-hydroxy-2-methylpyran-4-one
• CAS: 644-46-2
• 化学式: C₆H₆O₃
• mdl: MFCD04125897
• 分子量: 126.112
• InChiKey: IQXWFHDFTAZGNB-UHFFFAOYSA-N

物化性质

• 熔点：
  166 °C
• 沸点：
  285.5±40.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（少量）、DMSO（少量）、甲醇（少量）
• 保留指数：
  1139;1142

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  | 室温 |

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 5-Hydroxy-2-Methyl-4H-Pyran-4-One
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
For the full text of the H-Statements mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 126,11 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
5-Hydroxy-2-Methyl-4H-Pyran-4-One
Acute Tox. 4; H302 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
5-Hydroxy-2-Methyl-4H-Pyran-4-One
Xn, R22 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
No data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting if necessary.
Further information
No data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): Non Combustible Solids
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour No data available
c) Odour Threshold No data available
d) pH No data available
e) Melting point/freezing No data available
point
f) Initial boiling point and No data available
boiling range
g) Flash point No data available
h) Evaporation rate No data available
i) Flammability (solid, gas) No data available
j) Upper/lower No data available
flammability or
explosive limits
k) Vapour pressure No data available
l) Vapour density No data available
m) Relative density No data available
n) Water solubility No data available
o) Partition coefficient: n- No data available
octanol/water
p) Auto-ignition No data available
temperature
q) Decomposition No data available
temperature
r) Viscosity No data available
s) Explosive properties No data available
t) Oxidizing properties No data available
Other safety information
No data available

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SECTION 10: Stability and reactivity
Reactivity
No data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
No data available
Conditions to avoid
No data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
No data available
Skin corrosion/irritation
No data available
Serious eye damage/eye irritation
No data available
Respiratory or skin sensitisation
No data available
Germ cell mutagenicity
No data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
No data available
Specific target organ toxicity - single exposure
No data available
Specific target organ toxicity - repeated exposure
No data available
Aspiration hazard
No data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
No data available
Persistence and degradability
No data available
Bioaccumulative potential
No data available
Mobility in soil
No data available
Results of PBT and vPvB assessment
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
Other adverse effects
No data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
No data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
No data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
H302 Harmful if swallowed.
Full text of R-phrases referred to under sections 2 and 3
Xn Harmful
R22 Harmful if swallowed.
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

异麦芽醇可以作为有机合成中间体和医药中间体，主要应用于实验室研发和化工生产过程中。

反应信息

• 作为反应物：
  描述：

  别麦芽酚 在 盐酸 、 sodium hydroxide 、 对甲苯磺酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 52.0h， 生成 1,6-dimethyl-2-(4'-N-n-propylsuccinamido)methyl-3-benzyloxypyridin-4(1H)-one
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Novel 2-Substituted 3-Hydroxypyridin-4-ones:  Structure−Activity Investigation of Metalloenzyme Inhibition by Iron Chelators

  摘要：

  A range of novel 3-hydroxypyridin-4-ones with different R(2) substitutents has been synthesized for the investigation of the structure-activity relationship between the chemical nature of the ligand and the inhibitory activity of the iron-containing metalloenzyme 5-lipoxygenase. Results indicate that the molecular dimensions, together with the lipophilicity, have a critical impact on the ability of this class of chelator to inhibit 5-lipoxygenase. Hydrophilic ligands with a bulky R(2) substitutent tend to be weak inhibitors; thus 1,6-dimethyl-2-(4'-N-n-propylsuccinamido)methyl-3-hydroxypyridin-4(1H)-one (22b) which has the largest R(2) substitutent only caused 2% inhibition of the enzyme activity after 30 min incubation at 110 muM IBE (iron-binding equivalents), as compared with deferiprone which caused 40% inhibition of the enzyme activity, under the same conditions.

  DOI：

  10.1021/jm010817i
• 作为产物：
  描述：

  曲酸 在 盐酸 、 氯化亚砜 、 锌 作用下， 以 水 为溶剂， 生成 别麦芽酚
  参考文献：
  名称：

  3-羟基吡喃-4-酮和3-羟基吡啶-4-酮衍生物作为HIV-1整合酶抑制剂的合成，分子建模和生物学研究

  摘要：

  背景：尽管通过靶向HIV整合酶（IN）（一种针对HIV-1的有前途且广为人知的药物靶标）来治疗HIV-1感染的抗逆转录病毒化合物的发现取得了进展，但是，仍然越来越需要增加针对HIV的武器库，为避免耐药性问题。 目的：为了开发新型的HIV-1 IN抑制剂，已经合理设计和合成了一系列3-羟基-吡喃-4-酮（HP）和3-羟基-吡啶-4-酮（HPO）衍生物。 方法：为了提供新型化合物的重要表征，使用新型HIV-1 IN / DNA二元3D模型进行了深入的计算分析，以研究新构想的分子与IN的结合模式。使用原型泡沫病毒（PFV）DNA作为结构模板生成3D模型，将病毒的多脱氧核糖核酸链置于HIV-1 IN同源性模型中。此外，进行了一系列体外试验，包括HIV-1活性抑制，HIV-1 IN活性抑制，HIV-1 IN链转移活性抑制和细胞毒性。 结果：生物测定结果表明，大多数HP类似物（包括HPa，HPb，HP

  DOI：

  10.2174/1573406415666181219113225

文献信息

• IDO INHIBITORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20160289171A1

  公开（公告）日：2016-10-06

  There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the invention.

  已披露的化合物可调节或抑制吲哌酮胺2,3-二氧化酶（IDO）的酶活性，含有该化合物的药物组合物以及利用本发明的化合物治疗增殖性疾病，如癌症、病毒感染和/或炎症性疾病的方法。
• [EN] COMPOSITIONS AND METHODS FOR INHIBITING INFLUENZA RNA POLYMERASE PA ENDONUCLEASE<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR INHIBER L'ENDONUCLÉASE DE LA PA DE L'ARN POLYMÉRASE DE LA GRIPPE
  申请人：UNIV CALIFORNIA

  公开号：WO2017156194A1

  公开（公告）日：2017-09-14

  There are provided inter alia metalloenzyme inhibitors, such as inhibitors of influenza A RNA dependent RNA polymerase PA subunit endonuclease, and methods of synthesis and use of the same.

  其中提供了金属酶抑制剂，例如流感A病毒RNA依赖性RNA聚合酶PA亚基内切酶的抑制剂，以及其合成和使用方法。
• [EN] HYDROXYLATED TROPOLONE INHIBITORS OF NUCLEOTIDYL TRANSFERASES IN HERPESVIRUS AND HEPATITS B AND USES THEREFOR<br/>[FR] INHIBITEURS HYDROXYLÉS DE TROPOLONE DE NUCLÉOTIDYL-TRANSFÉRASES UTILISÉS DANS LE TRAITEMENT DU VIRUS DE L'HERPÈS ET DE L'HÉPATITE B ET LEURS UTILISATIONS
  申请人：UNIV SAINT LOUIS

  公开号：WO2016201243A1

  公开（公告）日：2016-12-15

  The present disclosure relates to inhibitors of herpesvirus nucleic acid metabolism and inhibitors of Hepatitis B virus. Also provided are methods of treatment using these agents.

  本公开涉及抑制疱疹病毒核酸代谢和乙型肝炎病毒的抑制剂。还提供了使用这些药剂的治疗方法。
• Mannich base derivatives of 3-hydroxy-6- methyl-4H-pyran-4-one with antimicrobial activity
  作者：DEMET US、BARKIN BERK、ENİSE ECE GÜRDAL、NİHAN AYTEKİN、ZÜHTÜ TANIL KOCAGÖZ、BERRAK ÇAĞLAYAN、IŞIL KURNAZ、DİLEK DEMİR EROL

  DOI：10.3906/kim-0908-214

  日期：——

  A series of 3-hydroxy-6-methyl-2-[(substitutedpiperidine-1-yl) methyl]-4H-pyran-4-one structured compounds were synthesized by reacting 5-hydroxy-2-methyl-4H-pyran-4-one with suitable piperidine derivatives using Mannich reaction conditions. Antibacterial activities of the compounds for E. coli ATCC 25922, S. paratyphi ATCC BAA-1250, S. flexneri ATCC 12022, E. gergoviae ATCC 33426, and M. smegmatis ATCC 14468 were assessed in vitro by the broth dilution method for determination of minimum inhibitory concentration (MIC). In addition, their inhibitory effects over DNA gyrase enzyme were evaluated using a DNA gyrase supercoiling assay. All the synthesized compounds showed a MIC value of either 8 or 16 \mu g/mL for M. smegmatis, whereas minimum to moderate activity was achieved for the others. Those tested in the supercoiling assay had at best a very mild inhibition of the enzyme. This series deserves further attention for testing over Mycobacterium species and topoisomerase II inhibition to develop new lead drugs to treat non-tuberculous mycobacterial infections.

  通过在曼尼希反应条件下将5-羟基-2-甲基-4H-吡喃-4-酮与适宜的哌啶衍生物反应，合成了一系列具有3-羟基-6-甲基-2-[(取代哌啶-1-基)甲基]-4H-吡喃-4-酮结构的化合物。通过肉汤稀释法在体外评估了这些化合物对大肠杆菌ATCC 25922、沙门氏菌副伤寒亚种ATCC BAA-1250、福氏志贺菌ATCC 12022、杰戈维亚埃希氏菌ATCC 33426和耻垢分枝杆菌ATCC 14468的抗菌活性，以确定最小抑制浓度（MIC）。此外，还使用DNA促旋酶超螺旋测定法评估了它们对DNA促旋酶的抑制效果。所有合成的化合物对耻垢分枝杆菌的MIC值均为8或16 μg/mL，而对其他菌种则表现出最低至中等的活性。在超螺旋测定中测试的这些化合物对酶的最大抑制作用也是极其轻微的。这一系列化合物值得进一步关注，用于测试对分枝杆菌属物种和拓扑异构酶II的抑制作用，以开发治疗非结核性分枝杆菌感染的新型先导药物。
• Development of dual inhibitors targeting pyruvate dehydrogenase kinases and human lactate dehydrogenase A: High-throughput virtual screening, synthesis and biological validation
  作者：Sichuan Xiang、Ding Huang、Qiaolin He、Jie Li、Kin Yip Tam、Shao-Lin Zhang、Yun He

  DOI：10.1016/j.ejmech.2020.112579

  日期：2020.10

  Pyruvate dehydrogenase kinases (PDKs) and lactate dehydrogenase A (LDHA) play crucial roles in promotion of glycolysis, thus the inhibition of both enzymes is considered a promising strategy for developing of anticancer therapeutics. Herein, we describe the first discovery of series novel dual inhibitors targeting PDKs and LDHA. We identified 6 hits from a library database containing 485465 compounds through

  大多数癌细胞具有从氧化磷酸化到细胞质糖酵解的葡萄糖代谢改变的特征。丙酮酸脱氢酶激酶（PDKs）和乳酸脱氢酶A（LDHA）在促进糖酵解中起关键作用，因此抑制这两种酶被认为是开发抗癌治疗剂的有希望的策略。在这里，我们描述了针对PDK和LDHA的系列新型双重抑制剂的首次发现。通过高通量虚拟筛选分析，我们从包含485465种化合物的数据库数据库中鉴定了6个匹配项。领先的优化方法使我们能够发现两种化合物，即20e和20k，它们分别抑制了IC 50值为0.8和1.6μM的PDK，并抑制了IC 50的LDHA。值分别为0.15和0.7μM。同时，这两种化合物降低了A549细胞的增殖，EC 50值为13.2和15.7μM。此外，20e和20k减少了乳酸的形成，增加了氧气的消耗，表明这两种化合物调节了癌细胞中的葡萄糖代谢途径。