D-(-)-苏糖 | 95-43-2

• 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: D-(-)-苏糖
• 中文别名: D-苏糖
• 英文名称: D-threose
• 英文别名: threose；(2S,3R)-2,3,4-trihydroxybutanal
• CAS: 95-43-2
• 化学式: C₄H₈O₄
• 分子量: 120.105
• InChiKey: YTBSYETUWUMLBZ-QWWZWVQMSA-N

物化性质

• 熔点：
  130℃
• 比旋光度：
  D20 -12.3° (20 min, c = 4)
• 沸点：
  144.07°C (rough estimate)
• 密度：
  1.0500 (rough estimate)
• 溶解度：
  可溶于甲醇（轻微）、水（可溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2912491000
• 储存条件：
  0-10°C；请避免加热。

SDS

Name:	D(-)-Threose Material Safety Data Sheet
Synonym:
CAS:	95-43-2

Section 1 - Chemical Product MSDS Name:D(-)-Threose Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
95-43-2	D(-)-Threose		202-418-0

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical 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.

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Section 7 - HANDLING and STORAGE
Handling:
Use with adequate ventilation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Deep freeze (below -20C).

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 95-43-2: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Viscous liquid
Color: white - yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 69-72 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Soluble.
Specific Gravity/Density:
Molecular Formula: C5H10O4
Molecular Weight: 134.13

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 95-43-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
D(-)-Threose - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
No information available.

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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# 95-43-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 95-43-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 95-43-2 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：

  D-(-)-苏糖 在 硝酸 作用下， 生成 D-酒石酸
  参考文献：
  名称：

  Perceptions of Depression in a Community Sample in Dubai

  摘要：

  尽管描述抑郁症的词语可能并非所有文化都存在，但抑郁症的症状却存在。在迪拜的阿拉伯社区进行的一项研究中，我们开展了四个焦点小组讨论，分别是两个男性和两个女性，以确定人们用于描述抑郁症的术语和描述，他们将哪些症状与之相关联，他们对其原因的看法，以及应对它的策略。所有参与者都认识符合抑郁症描述的人。确定的抑郁症主要症状包括：社交退缩、感到害怕、易怒、失眠、食欲不振、悲伤、哭泣、过度思考、感到无聊和对性的兴趣丧失。确定的抑郁症原因包括：家庭和社会压力、人际关系、缺乏支持、婚姻冲突以及与子女的问题。确定的最有效应对策略是去宗教场所并与宗教专业人士交谈。

  DOI：

  10.1177/136346150103800204
• 作为产物：
  描述：

  β-D-threofuranose 以 重水 为溶剂， 生成 D-(-)-苏糖
  参考文献：
  名称：

  呋喃糖环异构化：5-脱氧戊糖和5-O-甲基戊糖的动力学研究

  摘要：

  使用13C饱和转移NMR（st-nmr）光谱研究了5-脱氧-L-戊糖（1-4）和5-O-甲基-D-戊糖（5-8）在水溶液中的异构化作用在异头碳原子上被13 C取代的化合物。这些化合物在相同的溶液条件下（50mM乙酸盐缓冲液，pH值为60，pH 4.0）已获得开环（k开）和闭环（k关）的单向速率常数，并将其与实测值进行了比较。 D-四聚体（9和10）和四个D-戊糖5-磷酸（11-14）。基于这些比较，已揭示了呋喃糖结构与反应性之间的几种相关性，并提出了模型来解释观察到的化合物的动力学行为（1-10）。还通过比较5-脱氧-L-（1-13C）-Lyose和5-O-甲基-D-（1-13C）Lyxose的行为，研究了环外结构对酸催化的速率常数的影响。已经考虑确定可能在确定结构对异构化反应性的影响中起作用的因素（焓和熵）。

  DOI：

  10.1016/0008-6215(88)80002-8

文献信息

• Kinetics of oxidation of monosaccharides with cerium(IV)
  作者：Pentti O.I. Virtanen、Raija Lindroos、Eija Oikarinen、Juhani Vaskuri

  DOI：10.1016/0008-6215(87)80265-3

  日期：1987.9

  Abstract The kinetics of the oxidation of d -galactose, d -glucose, d -mannose, d -fructose, l -sorbose, l -arabinose, d -ribose, and d -xylose with cerium(IV) in perchloric acid were studied. Two complexes were found to form in each case. The first complex forms in a pre-quilibrium reaction during mixing in the stopped-flow apparatus. Michaelis-Menten kinetics were observed for this oxidation. The values

  摘要研究了高氯酸中铈（Ⅳ）对d-半乳糖，d-葡萄糖，d-甘露糖，d-果糖，l-山梨糖，l-阿拉伯糖，d-核糖和d-木糖的氧化动力学。发现在每种情况下都会形成两个复合物。在停止流设备中混合期间，第一络合物在平衡前反应中形成。观察到该氧化的Michaelis-Menten动力学。在1.0 m HClO 4中确定络合物形成和解离速率常数的值。离解部分涉及第一配合物的氧化，部分涉及第二更稳定的配合物的形成。第二种络合物的氧化速度比第一种络合物慢得多，并且在1.0 m HClO 4中再次确定了拟一级反应速率常数。瓣在0.1 m到1的范围内被证明是几乎恒定的。
• A Mutant D-Fructose-6-Phosphate Aldolase (Ala129Ser) with Improved Affinity towards Dihydroxyacetone for the Synthesis of Polyhydroxylated Compounds
  作者：José A. Castillo、Christine Guérard-Hélaine、Mariana Gutiérrez、Xavier Garrabou、Martine Sancelme、Melanie Schürmann、Tomoyuki Inoue、Virgil Hélaine、Franck Charmantray、Thierry Gefflaut、Laurence Hecquet、Jesús Joglar、Pere Clapés、Georg A. Sprenger、Marielle Lemaire

  DOI：10.1002/adsc.200900772

  日期：——

  is particularly useful in carboligation multi‐step cascade synthesis of polyhydroxylated complex compounds. Production of the mutant protein was also improved for its convenient use in synthesis. Several carbohydrates and nitrocyclitols were efficiently prepared, demonstrating the versatile potential of FSA A129S as biocatalyst in organic synthesis.

  研究了大肠杆菌D-果糖-6-磷酸醛缩酶（FSA）的突变体FSA A129S，其对醛醇加成反应中供体底物二羟基丙酮（DHA）的催化效率得到了提高，可用于合成应用。FSA A129S的DHA的k cat / K M值比FSA野生型（FSA wt）高出17倍。另一方面，对于羟丙酮作为供体底物，发现FSA A129S的效率比FSA wt低3.5倍。此外，FSA A129S还接受了乙醇醛（GA）作为供体底物，其亲和力比FSA wt低3.3倍。两种FSA wt的差异选择性FSA A129S和GA的FSA A129S使它们成为互补的生物催化剂，可以控制供体和受体的作用，这在多羟基化复合化合物的碳多步级联碳多步合成中特别有用。突变蛋白的生产也得到了改进，因为它可方便地用于合成。有效地制备了几种碳水化合物和硝基环糖醇，证明了FSA A129S作为有机合成中的生物催化剂具有多种用途。
• Thiazolidine Peracetates: Carbohydrate Derivatives that Readily Assign <i>cis-</i>,<i>trans</i>-2,3-Monosaccharides by Gas Chromatography–Mass Spectrometry Analysis
  作者：Neil. P. J. Price、Trina M. Hartman、Karl E. Vermillion

  DOI：10.1021/acs.analchem.8b00976

  日期：2018.7.3

  nonpolar thiazolidines peracetate (TPA) derivatives are analyzed by gas chromatography and electron impact mass spectrometry (GC/EI-MS), each aldose giving rise to two TPA geometric isomers. The quantitative ratio of these diastereomers is dependent upon whether the parent monosaccharide is cis-2,3-(Rib, Lyx, Man, All, Gul, and Tal), or trans-2,3-aldose (Xyl, Ara, Glc, Gal, Ido, and Alt). TPAs generate observed

  描述了一组新颖的碳水化合物衍生物，其以低纳摩尔浓度唯一地分配了顺式/反式-2,3-醛糖立体异构体。来自多糖或寡糖水解的醛糖戊糖，醛糖己糖或组分醛糖与吡啶中的半胱胺反应，得到定量形成的噻唑烷，其随后在一锅法反应中被过乙酰化。通过气相色谱和电子冲击质谱（GC / EI-MS）分析非极性噻唑烷过乙酸（TPA）衍生物，每种醛糖产生两个TPA几何异构体。这些非对映异构体的定量比率取决于母体单糖是顺式-2,3-（Rib，Lyx，Man，All，Gul和Tal）还是反式-2,3-醛糖（Xyl，Ara，Glc，Gal，Ido和Alt）。TPA产生观察到的EI-MS碎片离子，其特征是母糖的C1-C2和C3-C4键断裂。这已被用于估计微生物细胞壁碳水化合物的代谢标记的程度，尤其是进入定义的异头碳以及醛缩酶/酮醇酶催化的重排过程中。
• A Kinetic Photometric Assay for the Quantification of the Open‐Chain Content of Aldoses
  作者：Hubert Kalaus、Alexander Reichetseder、Verena Scheibelreiter、Florian Rudroff、Christian Stanetty、Marko D. Mihovilovic

  DOI：10.1002/ejoc.202001641

  日期：2021.5.14

  An operationally simple UV‐based kinetic assay allows the accurate determination of the minute proportions (<1 %) of the open‐chain forms (OCC) of aldoses in equilibrium with the dominant ring forms. The OCC‐data of all parent aldoses has been determined with this new ABAO‐assay and is fully consistent with the literature gold standard, allowing extension into first practical synthetic challenges.

  操作简单的基于 UV 的动力学测定可以准确测定与主要环形式平衡的醛糖开链形式 (OCC) 的微小比例 (<1%)。所有母体醛糖的 OCC 数据均已通过这种新的 ABAO 测定法确定，并且与文献金标准完全一致，允许扩展到第一个实际合成挑战。
• The degradation of l-threose at Maillard reaction conditions
  作者：Elaine Yinan Li、Milton S. Feather

  DOI：10.1016/0008-6215(94)84225-6

  日期：1994.3

  L-Threose, a comparatively unstable aldose, is produced from L-ascorbic acid in the presence of oxygen and participates vigorously in Maillard reactions, even at comparatively mild conditions. In the present study, the degradation of L-threose at pH 7.0 alone, in the presence of N-alpha-acetyl-L-lysine, and at pH 2.0 alone at 37 degrees C was investigated by identification of some of the products produced

  L-苏糖，一种相对不稳定的醛糖，是在氧气存在下由L-抗坏血酸产生的，即使在相对温和的条件下，也能强烈参与美拉德反应。在本研究中，通过鉴定一些在乙醇中产生的产物，研究了仅在pH 7.0时，在N-α-乙酰基-L-赖氨酸存在下，以及仅pH 2.0时在37℃下L-苏糖的降解情况。通过GLC和GLC-MS进行反应。在鉴定出的化合物中，有3-脱氧-四-2-戊糖（1），预测的碱重排产物，其衍生自1（2,4-二羟基丁酸酯，4-碳间糖酸）以及甘油醛。同位素示踪剂研究清楚地表明，甘油醛是由起始L-苏糖分子中C-1的丢失而产生的。