L-葡糖酸-1,5-内酯 | 52153-09-0

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: L-葡糖酸-1,5-内酯
• 英文名称: L-glucono-1,5-lactone
• 英文别名: glucono lactone；(3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
• CAS: 52153-09-0
• 化学式: C₆H₁₀O₆
• 分子量: 178.142
• InChiKey: PHOQVHQSTUBQQK-KLVWXMOXSA-N

物化性质

• 熔点：
  142-144 °C(lit.)
• 沸点：
  230.35°C (rough estimate)
• 密度：
  1.3253 (rough estimate)
• 溶解度：
  DMSO（轻微）、水（轻微、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 海关编码：
  2932999099

SDS

Name:	L-Glucono-1 5-Lactone Material Safety Data Sheet
Synonym:	None
CAS:	52153-09-0

Section 1 - Chemical Product MSDS Name:L-Glucono-1 5-Lactone Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
52153-09-0	L-Glucono-1,5-Lactone	ca 100	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Moisture sensitive.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: 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. Wash mouth out with 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 agent most appropriate to extinguish fire. Do NOT get water inside containers. 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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation. Do not get water inside containers.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Do not allow contact with water. Keep from contact with moist air and steam.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Storage under a nitrogen blanket has been recommended. Store protected from moisture.

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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# 52153-09-0: 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: Powder
Color: white
Odor: odorless
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 142 - 144 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: soluble
Specific Gravity/Density:
Molecular Formula: C6H10O6
Molecular Weight: 178.0664

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, moisture, exposure to moist air or water.
Incompatibilities with Other Materials:
Moisture, strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 52153-09-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
L-Glucono-1,5-Lactone - 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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 52153-09-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 52153-09-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 52153-09-0 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：

  L-葡糖酸-1,5-内酯 在 sodium tetrahydroborate 、 Amberlite IR-120 H⁺ form 、 Amberlite IR-45 OH^- form 、 硫酸 作用下， 反应 1.67h， 以53.7%的产率得到L-(-)-glucose
  参考文献：
  名称：

  Szarek, Walter A.; Hay, George W.; Vyas, Dolatrai M., Canadian Journal of Chemistry, 1984, vol. 62, p. 671 - 674

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2,3-O-isopropylidene-β-D-gulofuranosiduronic acid 在 镍 Dowex 50W-X₈ H⁺ form 、 氢气 作用下， 以 水 为溶剂， 以68.5%的产率得到L-葡糖酸-1,5-内酯
  参考文献：
  名称：

  Szarek, Walter A.; Hay, George W.; Vyas, Dolatrai M., Canadian Journal of Chemistry, 1984, vol. 62, p. 671 - 674

  摘要：

  DOI：

文献信息

• Confirmation of the structure of a glucono-1,4-lactone derivative obtained from silylation of glucono-1,5-lactone
  作者：Paul V. Murphy、Ciaran McDonnell、Ludger Hämig、Duncan E. Paterson、Richard J.K. Taylor

  DOI：10.1016/s0957-4166(02)00747-4

  日期：2003.1

  5-lactone and manno-1,5-lactone derivatives and other possible products has also been ruled out by synthesis of possible exo-glycal derivatives of these lactones using the Ramberg–Bäcklund rearrangement of the corresponding sulfones.

  葡糖醛-1，5-内酯的甲硅烷基化反应可根据所采用的反应条件而给出过甲硅烷基化的葡糖醛-1，5-内酯或过甲硅烷基化的1，4-内酯。2，3，5，6-四-O-（叔丁基二甲基甲硅烷基）-d-葡萄糖基-1，4-内酯的结构，是由葡萄糖基1，5-内酯与TBSOTf和X射线晶体学证实了二氯甲烷中的二甲基吡啶。通过使用相应砜的Ramberg-Bäcklund重排合成这些内酯的可能的糖基外衍生物，还排除了葡萄糖基-1,5-内酯和甘露-1,5-内酯衍生物及其他可能产物的形成。
• Triphenylphosphine derivative, production process therefor, palladium complex thereof, and process for producing biaryl derivative
  申请人：——

  公开号：US20030065208A1

  公开（公告）日：2003-04-03

  Provided are a novel triphenyl phosphine derivative synthesized from a triphenylphosphine and a hydroxy-containing lactone; a palladium and a nickel complexes comprising the derivative as a ligand; and a process for preparing a biaryl derivative using the complex as a catalyst. A product can be easily separated from a catalyst or a phosphorus compound, and biaryl derivative can be synthesized in a higher yield, by using the complex of the present invention as a catalyst.

  提供了一种新型的三苯基膦衍生物，通过三苯基膦和含羟基的内酯合成；一种以该衍生物为配体的钯和镍配合物；以及一种利用该配合物作为催化剂制备联苯衍生物的方法。通过使用本发明的复合物作为催化剂，产品可以很容易地与催化剂或磷化合物分离，联苯衍生物可以以更高的产率合成。
• PROCESS FOR PREPARATION OF ALDONIC ACIDS AND DERIVATIVES THEREOF
  申请人：Weymouth-Wilson Alexander Charles

  公开号：US20090112002A1

  公开（公告）日：2009-04-30

  A process for the preparation of L-gluconic acid or a salt thereof, comprises treating an aqueous solution of 6-bromo-6-deoxy-2,3-anhydro-D-manno-1,4-lactone with a base at a pH of at least 12 and at a temperature of 45 to 55° C. to obtain an aqueous solution of L-gluconic acid.

  一种制备L-葡萄糖酸或其盐的方法，包括将6-溴-6-去氧-2,3-脱水-D-曼诺-1,4-内酯的水溶液在pH至少为12且温度为45至55°C的条件下与碱处理，以获得L-葡萄糖酸的水溶液。
• Noncovalent Synthesis of Water-Soluble SCS PdII Pincer Assemblies
  作者：Henk-Jan van Manen、Roel H. Fokkens、Frank C. J. M. van Veggel、David N. Reinhoudt

  DOI：10.1002/1099-0690(200209)2002:18<3189::aid-ejoc3189>3.0.co;2-8

  日期：2002.9

  This article describes the noncovalent synthesis of water-soluble coordination assemblies based on SCS PdII pincer moieties. Two neutral solubilizing moieties, one based on a linear carbohydrate chain and the other on tetraethylene glycol residues, have been functionalized with pyridine and phosphane ligands. The coordination of the resulting molecules to various hydrophobic, cationic mono- and multimeric

  本文介绍了基于 SCS PdII 钳部分的水溶性配位组件的非共价合成。两个中性增溶部分，一个基于线性碳水化合物链，另一个基于四乙二醇残基，已经用吡啶和磷烷配体进行了功能化。已通过 1 H 和 31 P NMR 光谱以及 MALDI-TOF 质谱法研究了所得分子与各种疏水性、阳离子单聚体和多聚体 SCS PdII 钳系统的配位。通常，具有四甘醇链的组件在水中的溶解度高于包含线性糖部分的组件。用六种线性碳水化合物装饰的六针形核形成水凝胶。最后，
• The Aggregated Higher-Structure of 1,3 : 2,4-Di-<i>O</i>-benzylidene-D-sorbitol in Organic Gels
  作者：Seiji Yamasaki、Yukihiro Ohashi、Hisao Tsutsumi、Kaoru Tsujii

  DOI：10.1246/bcsj.68.146

  日期：1995.1

  1,3 : 2,4-Di-O-benzylidene-d-sorbitol (d-DBS) can cause gelation of organic solvents of a wide range of polarity into a gel state. The aggregated structures of d-DBS/organic solvent systems were studied, mainly by using IR, UV, and circular dichroism (CD) spectroscopy. In the case of the racemate Dl-DBS, no gel state was formed. In IR spectra of d-DBS and Dl-DBS in the solid state, the intensities of νOH and νCO absorption in d-DBS were found to be larger than those in Dl-DBS. It is assumed that the hydrogen bonding formed between an acetal oxygen and a hydroxyl group in the aggregation of d-DBS. From the changes in the IR spectra from solution into a gel state, we can conclude that the chirality and the hydrogen bonding of DBS molecules are essential for the formation of the gel. Comparing the gel-forming ability of d-DBS with its derivatives, 5- or 6-hydroxyl-group-blocked compounds by methyl group, the 6-hydroxyl group seems to be important in the formation of d-DBS aggregates. The results of UV spectra suggest that the benzene rings are ordered in a side by side arrangement. The molar ellipticities in CD spectra increased about 500 times during the change from the solution to the gel state. From these results, it is concluded that d-DBS forms a helical structure of thin fibrous crystals in the gel state.

  1,3 : 2,4-二-O-亚苄基-d-山梨糖醇（d-DBS）能使极性范围很广的有机溶剂凝胶化成凝胶状态。研究人员主要利用红外光谱、紫外光谱和圆二色性光谱（CD）对 d-DBS / 有机溶剂体系的聚集结构进行了研究。外消旋物 Dl-DBS 没有形成凝胶态。在固态 d-DBS 和 Dl-DBS 的红外光谱中，发现 d-DBS 中的νOH 和 νCO 吸收强度大于 Dl-DBS。由此推测，在 d-DBS 的聚集过程中，缩醛氧和羟基之间形成了氢键。根据从溶液到凝胶状态的红外光谱变化，我们可以得出结论：DBS 分子的手性和氢键是凝胶形成的关键。比较 d-DBS 与其衍生物、5-羟基或 6-羟基被甲基封端的化合物的凝胶形成能力，6-羟基似乎对 d-DBS 聚合物的形成很重要。紫外光谱的结果表明，苯环是并排有序排列的。在从溶液到凝胶状态的变化过程中，CD 光谱中的摩尔椭圆度增加了约 500 倍。从这些结果可以得出结论，d-DBS 在凝胶状态下形成了一种螺旋结构的纤维状薄晶体。