甲基葡萄糖 | 13224-94-7

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基葡萄糖
• 中文别名: 3-O-甲基-D-吡喃葡萄糖；3-O-甲基-D-葡萄糖
• 英文名称: 3-O-methyl-α-D-glucopyranose
• 英文别名: 3-O-Methyl-alpha-D-glucopyranose；(2S,3R,4S,5R,6R)-6-(hydroxymethyl)-4-methoxyoxane-2,3,5-triol
• CAS: 13224-94-7
• 化学式: C₇H₁₄O₆
• 分子量: 194.185
• InChiKey: SCBBSJMAPKXHAH-OVHBTUCOSA-N

物化性质

• 熔点：
  167-169 °C(lit.)
• 比旋光度：
  +54～+58°(D/20℃) (c=1, dil. NH4OH)
• 沸点：
  250.62°C (rough estimate)
• 密度：
  1.2501 (rough estimate)
• 溶解度：
  DMSO（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25,S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29400090

SDS

Name:	3-O-Methylglucose 99% Material Safety Data Sheet
Synonym:	3-O-Methyl-alpha-D-glucopyranos
CAS:	13224-94-7

Section 1 - Chemical Product MSDS Name:3-O-Methylglucose 99% Material Safety Data Sheet
Synonym:3-O-Methyl-alpha-D-glucopyranos

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13224-94-7	3-O-Methylglucose	99	236-197-7

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 13224-94-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 167.00 - 169.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: Not available.
Molecular Formula: C7H14O6
Molecular Weight: 194.18

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13224-94-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-O-Methylglucose - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 13224-94-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13224-94-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13224-94-7 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  甲基葡萄糖 在 palladium on activated charcoal 吡啶 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 氢气 、 potassium carbonate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 生成 Benzoic acid (S)-[(4S,4aS,6R,7R,8R,8aR)-7-acetoxy-6-(2,2-dimethyl-propionyloxymethyl)-8-methoxy-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester
  参考文献：
  名称：

  Synthesis and biological activity of artificial analogs of mycalamide A

  摘要：

  Artificial analogs of mycalamide A, a potent antitumor and antiviral compound isolated from a New Zealand marine sponge, were synthesized and their biological activities were tested. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00365-x
• 作为产物：
  描述：

  双丙酮葡萄糖 生成 甲基葡萄糖
  参考文献：
  名称：

  糖苷的酸水解

  摘要：

  摘要确定了酸催化甲基β-D-吡喃葡萄糖苷和龙胆二糖的2-，3-，4-和6-O-甲基衍生物水解的速率系数和动力学参数。所有的单甲基醚的水解速度都比未取代的化合物慢一些，两个系列的速率均以3-O-甲基> 2-O-甲基> 4-O-甲基> 6-O甲基的顺序降低。如果单分子水解是通过环状碳酸根离子进行的，则结果与预期的结果相符。因此，他们提供了支持该机制的更多证据。

  DOI：

  10.1016/s0008-6215(00)81150-7

文献信息

• Inositol Biotransformation
  申请人：UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS

  公开号：US20160168607A1

  公开（公告）日：2016-06-16

  Disclosed is a method of preparing pure or substantially pure D-myo-inositol-3-phosphate from glucose-6-phosphate and/or fructose-6-phosphate. The method may also be applied to protected and/or derivative forms of glucose-6-phosphate and/or fructose-6-phosphate so as to form protected/derivative forms of D-myo-inositol-3-phosphate, for use in further chemical reactions. The enzyme D-myo-inositol-3-phosphate synthase (INO1) is contacted with the glucose-6-phosphate and/or fructose-6-phosphate to generate labeled or unlabeled, protected or unprotected D-myo-inositol-3-phosphate, which may be further reacted and/or purified.

  披露了一种从葡萄糖-6-磷酸和/或果糖-6-磷酸制备纯净或基本纯净的D-肌醇-3-磷酸的方法。该方法也可应用于葡萄糖-6-磷酸和/或果糖-6-磷酸的保护形式和/或衍生物形式，以形成D-肌醇-3-磷酸的保护/衍生物形式，用于进一步的化学反应。D-肌醇-3-磷酸合酶（INO1）酶与葡萄糖-6-磷酸和/或果糖-6-磷酸接触，以生成标记的或未标记的、保护的或未保护的D-肌醇-3-磷酸，该磷酸可进一步反应和/或纯化。
• [EN] GLYCOSAMINOGLYCAN (GAG) MIMETICS<br/>[FR] COMPOSES MIMETIQUES DU GLYCOSAMINOGLYCANE (GAG)
  申请人：PROGEN IND LTD

  公开号：WO2005061523A1

  公开（公告）日：2005-07-07

  The invention relates to compounds that are designed to mimic the structure of GAGs; methods for the preparation of the compounds; compositions comprising the compounds; and use of the compounds and compositions thereof for the anti-angiogenic, anti-metastatic, anti-inflammatory, anticoagulant, antithrombotic, and/or antimicrobial treatment of a mammalian subject.

  本发明涉及旨在模仿GAGs结构的化合物；制备这些化合物的方法；包含这些化合物的组合物；以及将这些化合物及其组合物用于哺乳动物主体的抗血管生成、抗转移、抗炎、抗凝血、抗血栓和/或抗微生物治疗的用途。
• 31P-N.m.r. spectroscopy in wood chemistry. Phosphite derivatives of carbohydrates
  作者：Yuri Archipov、Dimitris S. Argyropoulos、Henry Bolker、Cyril Heitner

  DOI：10.1016/0008-6215(91)80005-8

  日期：1991.11

  and model compounds for lignin-carbohydrate complexes were reacted with 1,3,2-dioxaphospholanyl chloride, and the 31P-n.m.r. spectra of the derivatives were obtained in order to correlate the signals with the structural details of the compounds. The derivatives of most of the carbohydrates exhibited spectra containing well resolved signals in the range 138-132 p.p.m., and the number of lines accorded

  摘要使选定的无环和环状多元醇，单糖，二糖，高级寡糖和木质素-碳水化合物配合物的模型化合物与1,3,2-二氧杂磷酰氯酰氯反应，得到衍生物的31P-nmr光谱以使它们相互关联。表示化合物的结构细节。大多数碳水化合物的衍生物显示出的光谱包含在138-132 ppm范围内的分辨良好的信号，并且谱线数与相应化合物中的羟基数相符。单糖衍生物中C-1处磷原子的化学位移值是所涉及的端基异构体的特征。由于完全分解的光谱分别具有糖和木质素相关部分的特征信号，获得了相关模型化合物的一部分，该方法似乎非常适合于对木质素-碳水化合物复合物衍生的分子进行结构解析。对环糊精（环麦芽六-，庚-和八糖）进行了衍生化处理，检查后得出的光谱彼此之间存在显着差异。
• [EN] INHIBITORS OF ALDOSE REDUCTASE<br/>[FR] INHIBITEURS DE L'ALDOSE RÉDUCTASE
  申请人：APPLIED THERAPEUTICS INC

  公开号：WO2020205846A1

  公开（公告）日：2020-10-08

  The present disclosure relates to novel compounds and pharmaceutical compositions thereof, and methods for promoting healthy aging of skin, the treatment of skin disorders, the treatment of cardiovascular disorders, the treatment of renal disorders, the treatment of angiogenesis disorders, such as cancer, treatment of tissue damage, such as non-cardiac tissue damage, the treatment of evolving myocardial infarction, the treatment of ischemic injury, and the treatment of various other disorders, such as complications arising from diabetes with the compounds and compositions of the invention. Other disorders can include, but are not limited to, atherosclerosis, cardiomyopathy, coronary artery disease, diabetic nephropathy, diabetic neuropathy, diabetic retinopathy, diabetic cardiomyopathy, infections of the skin, peripheral vascular disease, stroke, galactosemia, asthma, PMM2-CDG and the like.

  本公开涉及新颖化合物及其药物组合物，以及促进皮肤健康老化、治疗皮肤疾病、心血管疾病、肾脏疾病、血管生成障碍（如癌症）、组织损伤治疗（如非心脏组织损伤）、心肌梗死演变治疗、缺血性损伤治疗以及利用本发明的化合物和组合物治疗糖尿病引起的并发症等方法。其他疾病可能包括但不限于动脉粥样硬化、心肌病、冠状动脉疾病、糖尿病肾病、糖尿病神经病变、糖尿病视网膜病变、糖尿病心肌病、皮肤感染、外周血管疾病、中风、半乳糖血症、哮喘、PMM2-CDG等。
• Oxidation of carbohydrates of biological importance by the aquachromium(IV) ion
  作者：Juan Carlos González、María Florencia Mangiameli、Agostina Crotta Asis、Sebastián Bellú、Luis F. Sala

  DOI：10.1016/j.poly.2012.09.042

  日期：2013.1

  Abstract The oxidation reactions kinetics of a series of related saccharides by aqua-oxo chromium(IV) ion, (H 2 O) 5 Cr IV O 2+ , were carried out in perchloric acid aqueous solutions. These reactions yield superoxochromium(III) ion, CrO 2 2+ , providing evidence that the two-electron reduction of CrO 2+ to Cr 2+ occurred in a single step. In all of these reactions, Cr 2+ is the immediate product and

  摘要在高氯酸水溶液中，通过水合氧化铬（IV）离子（H 2 O）5 Cr IV O 2+进行了一系列相关糖类的氧化反应动力学。这些反应产生了超氧铬（III）离子CrO 2 2+，提供了证据表明CrO 2+到Cr 2+的两电子还原是一步完成的。在所有这些反应中，Cr 2+是直接产物，当存在过量的氧气时可能被捕获为CrO 2 2+。在0.1–1.0 M范围内，不同醛糖和d-葡萄糖醇的双分子速率常数与[H +]无关。这些糖对CrO 2+还原的相对反应性是1-甲基-α-d-吡喃葡萄糖d-吡喃半乳糖‐ 3-O-甲基-d-吡喃葡萄糖〜6-脱氧-1-葡萄糖吡喃糖〜2-脱氧-d-吡喃葡萄糖〜d-吡喃葡萄糖d-吡喃葡萄糖d-葡萄糖醇。CrO 2+对醛糖酸（如d-葡萄糖酸）的氧化显示出相同的机理，但是当[H +]增加时，氧化还原过程受到强烈抑制。还确定了所选反应的活化参数。根据动力学结果，活化参数数据和氧化的有机产物，提出糖基被CrO

表征谱图