L-赤藓糖 | 533-49-3

• 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: L-赤藓糖
• 英文名称: L-erythrose
• 英文别名: (2S,3S)-2,3,4-trihydroxybutanal
• CAS: 533-49-3
• 化学式: C₄H₈O₄
• mdl: MFCD00064377
• 分子量: 120.105
• InChiKey: YTBSYETUWUMLBZ-DMTCNVIQSA-N

物化性质

• 熔点：
  164 °C
• 比旋光度：
  D24 +11.5° (8 min) +15.2° (120 min) +30.5° (final, c = 3): Felton, Freudenberg, J. Am. Chem. Soc. 57, 1640 (1935)
• 沸点：
  144.07°C (rough estimate)
• 密度：
  1.0500 (rough estimate)
• 闪点：
  113 °C
• 溶解度：
  少许溶于甲醇、可溶于水
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与不相容的材料及热源接触。

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
• 安全说明：
  S24/25
• 储存条件：
  密封储存，应存放在阴凉、干燥的库房中。

SDS

Name:	L(+)-Erythrose 96% Material Safety Data Sheet
Synonym:
CAS:	533-49-3

Section 1 - Chemical Product MSDS Name:L(+)-Erythrose 96% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
533-49-3	L(+)-Erythrose	96%	208-567-8

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. May be harmful if inhaled.
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:
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.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 533-49-3: 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: Clear liquid
Color: light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 164 deg C
Autoignition Temperature: Not available.
Flash Point: > 230 deg C (> 446.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Soluble.
Specific Gravity/Density:
Molecular Formula: C4H8O4
Molecular Weight: 120.11

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 533-49-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
L(+)-Erythrose - 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
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# 533-49-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 533-49-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 533-49-3 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

制备方法与用途

L-红细胞是一种含有醛糖碳水化合物的成分，它已被用于糖基化研究以及表征红细胞中的还原酶活性。

反应信息

• 作为反应物：
  描述：

  L-赤藓糖 在 溴 作用下， 生成 erythronic acid
  参考文献：
  名称：

  Ruff, Chemische Berichte, 1901, vol. 34, p. 1369

  摘要：

  DOI：
• 作为产物：
  描述：

  L-arabonic acid amide 在 alkaline sodium hypochlorite 作用下， 生成 L-赤藓糖
  参考文献：
  名称：

  Boeddener; Tollens, Chemische Berichte, 1910, vol. 43, p. 1649

  摘要：

  DOI：

文献信息

• Kinetics and mechanism of quinolinium dichromate mediated oxidation of sugar alcohols in Bronsted acid media
  作者：Satish Babu Kodali、Narendar Reddy Jakku、Chinna Rajanna Kamatala、Rajeshwar Rao Yerraguntla

  DOI：10.1002/kin.21339

  日期：2020.3

  Bronsted acid catalyzed oxidation of certain sugar alcohols (polyols) has been studied by quinolinium dichromate (QDC) using aqueous sulfuric, perchloric, and hydrochloric acids at different temperatures. At constant acidity, reaction kinetics revealed the second‐order kinetics with a first order in [Alcohol] and [QDC]. Zucker‐Hammett, Bunnett, and Bunnett‐Olsen criteria were used to analyze acid‐dependent

  重铬酸喹啉鎓（QDC）使用硫酸，高氯酸和盐酸水溶液在不同温度下研究了布朗斯台德酸催化某些糖醇（多元醇）的氧化。在恒定的酸度下，反应动力学在[酒精]和[QDC]中显示了一级动力学。Zucker-Hammett，Bunnett和Bunnett-Olsen标准用于分析酸依赖的速率加速。（日志Bunnett-Olsen的曲线ķ + ħ ν）与（ħ ν +日志[H + ]），和（日志ķ）与（ħ ν +日志[H + ]），得到的斜率值（φ和φ *分别> 0.47），表明在硫酸，高氯酸和盐酸水溶液存在下，水分子在QDC氧化醇氧化机理的缓慢步骤中起着质子传递剂的作用。
• 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 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。
• Evolved Thermostable Transketolase for Stereoselective Two-Carbon Elongation of Non-Phosphorylated Aldoses to Naturally Rare Ketoses
  作者：Marion Lorillière、Romain Dumoulin、Mélanie L’enfant、Agnès Rambourdin、Vincent Thery、Lionel Nauton、Wolf-Dieter Fessner、Franck Charmantray、Laurence Hecquet

  DOI：10.1021/acscatal.9b01339

  日期：2019.6.7

  TKgst for conversion of two tetroses (d-threose, l-erythrose), two pentoses (d-xylose, d-ribose), and two hexoses (d-allose, d-glucose), respectively. These six Cn aldoses as acceptor and HPA as donor substrates were transformed by the TKgst variants at 60 °C with practically complete conversion. The corresponding Cn+2 ketoses, including two hexuloses (d-tagatose, l-psicose), two heptuloses (d-altro-heptulose

  我们建议使用羟基丙酮酸（HPA）作为一种步骤，一步一步地将非磷酸化醛糖（C 4 –C 6）的碳原子延伸成相应的C n +2酮糖（C 6 –C 8）的一种环保，高效，立体选择性的方法。酮醇供体底物和来自嗜热脂肪热地芽孢杆菌（TK gst）的演化的热稳定转酮醇酶作为生物催化剂。与野生型TK gst相比，TK gst活性位点中两个或三个关键位置的同时位点饱和诱变（SSM）产生了有效的变体L382F / F435Y，R521Y / S385 / H462N和R521V / S385D / H462S。用于分别转化两个四糖（d-苏糖，l-赤藓糖），两个戊糖（d-木糖，d-核糖）和两个己糖（d-阿洛糖，d-葡萄糖）。这六种C n醛糖为受体，HPA为供体底物，在60°C被TK gst变体转化，几乎完全转化。相应的C n +2酮糖，包括两个己糖（d-塔格糖，l-庚糖），两个庚糖（d-硝基-庚糖，d - i
• Convergent <i>in situ</i> Generation of Both Transketolase Substrates <i>via</i> Transaminase and Aldolase Reactions for Sequential One‐Pot, Three‐Step Cascade Synthesis of Ketoses
  作者：Marion Lorillière、Christine Guérard‐Hélaine、Thierry Gefflaut、Wolf‐Dieter Fessner、Pere Clapés、Franck Charmantray、Laurence Hecquet

  DOI：10.1002/cctc.201901756

  日期：2020.2.6

  We describe an efficient three‐enzyme, sequential one‐pot cascade reaction where both transketolase substrates are generated in situ in a convergent fashion. The nucleophilic donor substrate hydroxypyruvate was obtained from l‐serine and pyruvate by a transaminase‐catalyzed reaction. In parallel, three different (2S)‐α‐hydroxylated aldehydes, l‐glyceraldehyde, d‐threose, and l‐erythrose, were generated

  我们描述了一种高效的三酶顺序单锅级联反应，其中两种转酮酶底物均以会聚方式原位产生。亲核供体底物羟基丙酮酸是通过转氨酶催化反应从l丝氨酸和丙酮酸获得的。平行地，通过简单的非手性化合物乙二醇醛和甲醛通过d生成了三种不同的（2 S）-α-羟基化醛基，l-甘油醛，d-苏糖和l-赤藓糖作为亲电子受体。果糖6-磷酸醛缩酶催化。从温度，酶比例和底物浓度方面研究了这三种酶的相容性。该方法的效率依赖于转酮醇酶反应的不可逆性，驱动可逆的氨基转移反应的转移并确保所有底物的完全转化。三个有价值（3小号，4小号）-ketoses，升-ribulose，ð -tagatose，和升以良好的收率与高非对映选择性得到-psicose。