2-酮-L-古洛糖酸 | 526-98-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-酮-L-古洛糖酸
• 中文别名: 2-酮基-L-古龙酸；2-酮基-L-古龙酸水合物
• 英文名称: 2-keto-L-gulonic acid
• 英文别名: (3S,4R,5S)-3,4,5,6-tetrahydroxy-2-oxohexanoic acid
• CAS: 526-98-7
• 化学式: C₆H₁₀O₇
• 分子量: 194.141
• InChiKey: VBUYCZFBVCCYFD-NUNKFHFFSA-N

物化性质

• 熔点：
  171 °C
• 沸点：
  550.6±50.0 °C(Predicted)
• 密度：
  1.757±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（少许）、水（少许）
• LogP：
  -3.08 at 22℃

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  135
• 氢给体数：
  5
• 氢受体数：
  7

安全信息

• 海关编码：
  2918990090
• 危险性防范说明：
  P264,P270,P301+P312,P330,P403,P501
• 危险性描述：
  H302
• 储存条件：
  | 温度 | 惰性气体 | | --- | --- | | 2-8°C |

SDS

Name:	2-Keto-L-gulonic acid 90% Material Safety Data Sheet
Synonym:	None Known
CAS:	526-98-7

Section 1 - Chemical Product MSDS Name:2-Keto-L-gulonic acid 90% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
526-98-7	2-Keto-L-gulonic acid	90%	208-403-5

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. Inhalation may be fatal as a result of spasm, inflammation, edema of the larynx and bronchi, chemical pneumonitis and pulmonary edema. May be harmful if inhaled.
May cause burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting.
Chronic:
Effects may be delayed.

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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. 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. Do NOT use mouth-to-mouth resuscitation.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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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.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
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:
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# 526-98-7: 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:
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: Crystalline powder
Color: beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 171 deg C dec.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Moderately Soluble.
Specific Gravity/Density:
Molecular Formula: C6H12O6
Molecular Weight: 180.0804

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation.
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# 526-98-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Keto-L-gulonic acid - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 526-98-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 526-98-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 526-98-7 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：

  2-酮-L-古洛糖酸 生成 维生素 C
  参考文献：
  名称：

  从受保护的 D-葡萄糖醇衍生物合成 L-抗坏血酸（维生素 C）

  摘要：

  摘要 D-葡萄糖醇的 1,3,2,4-二缩醛的间接阳极氧化产生 2-酮基-L-古洛糖酸的 3,5,4,6-二缩醛。其水解提供 L-xylo-2-hexulosonic 酸，因此通过内酯化提供 L-抗坏血酸。

  DOI：

  10.1080/00397919108021034
• 作为产物：
  描述：

  L-sorbopyranose 在 hyper-cross-linked polystyrene-Pt-THF 氧气 、 sodium carbonate 作用下， 反应 3.67h， 生成 2-酮-L-古洛糖酸
  参考文献：
  名称：

  Platinum-Containing Hyper-Cross-Linked Polystyrene as a Modifier-Free Selective Catalyst for l-Sorbose Oxidation

  摘要：

  Impregnation of hyper-cross-linked polystyrene (BPS) with tetrahydrofuran (THF) or methanol (ML) solutions containing platinic acid results in the formation of Pt(II) complexes within the nanocavities of HPS. Subsequent reduction of the complexes by H-2 yields stable Pt nanoparticles with a mean diameter of 1.3 nm in THF and 1.4 nm in ML. The highest selectivity (98% at 100% conversion) measured during the catalytic oxidation of L-sorbose in water is. obtained with the HPS-Pt-THF complex prior to H2 reduction. During an induction period of about 100 min, L-sorbose conversion is negligible while catalytic species develop in situ. The structure, of the catalyst isolated after the induction period is analyzed by X-ray diffraction, transmission electron microscopy, and X-ray photoelectron spectroscopy. Electron micrographs reveal a broad distribution of Pt nanoparticles, 71% of which measure less than or equal to 2.0 nm in diameter. These nanoparticles are most likely responsible for the high catalytic activity and selectivity observed. The formation of nanoparticles measuring up to 5.9 nm in diameter is attributed to the facilitated intercavity transport and aggregation of smaller nanoparticles in swollen HPS. The catalytic properties of these novel Pt nanoparticles are highly robust, remaining stable even after 15 repeated uses.

  DOI：

  10.1021/ja0107834
• 作为试剂：
  描述：

  2-酮-L-古洛糖酸 、 、 葡萄糖 在 2-酮-L-古洛糖酸 、 维生素 C 作用下， 反应 23.0h， 以NA-21, MA-10, and MB-6 were sequentially obtained by conventional mutagenesis的产率得到维生素 C
  参考文献：
  名称：

  Microbial process for producing L-ascorbic acid, D-erythorbic acid, and salts thereof

  摘要：

  一种生产L-抗坏血酸或D-赤藓糖酸，或在每种情况下其钠、钾或钙盐的方法，从2-酮基-L-古龙糖酸或2-酮基-D-葡萄糖酸，或在每种情况下其钠、钾或钙盐，其中包括将2-酮基-L-古龙糖酸或2-酮基-D-葡萄糖酸，作为游离酸或其钠、钾或钙盐，与热酸性微生物的细胞在pH为1到6之间的溶液中孵育，在温度从大约30℃到大约100℃之间，形成L-抗坏血酸或D-赤藓糖酸或其适当的盐，并从溶液中分离出该产品的过程。

  公开号：

  US20030105160A1

文献信息

• PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
  申请人：Philippe Michel

  公开号：US20100028280A1

  公开（公告）日：2010-02-04

  The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

  该发明涉及一种直发角蛋白纤维的拉直过程，包括：(i)将至少两种变性剂含有的拉直组合物涂抹到角蛋白纤维上的步骤，(ii)使用加热装置将角蛋白纤维的温度升高至110至250°C的步骤。
• Direct Amidation of Aldoses and Decarboxylative Amidation of α-Keto Acids: An Efficient Conjugation Method for Unprotected Carbohydrate Molecules
  作者：Chia-Ching Cho、Jia-Nan Liu、Chung-Hsun Chien、Jiun-Jie Shie、Ying-Chu Chen、Jim-Min Fang

  DOI：10.1021/jo802338k

  日期：2009.2.20

  With use of iodine as an appropriate oxidant, unprotected and unmodified aldoses undergo oxidative amidation with a variety of functionalized amines, α-amino esters, and peptides, whereas KDO, sialic acid, and other α-keto acids proceed with oxidative decarboxylation followed by in situ amidation. Glycoside bond and many other functional groups are inert under such mild reaction conditions. This reaction

  通过使用碘作为适当的氧化剂，未保护和未修饰的醛糖会与各种功能化的胺，α-氨基酯和肽进行氧化酰胺化，而KDO，唾液酸和其他α-酮酸会继续进行氧化脱羧反应原位酰胺化。在这种温和的反应条件下，糖苷键和许多其他官能团是惰性的。用于糖分子的直接连接的该反应方案在糖缀合物的一般和有效合成的发展中看起来是有希望的。
• Platinum Catalysts Modified by Adsorbed Amines: A New Method of Enhancing Rate and Selectivity ofl-Sorbose Oxidation
  作者：C. Brönnimann、Z. Bodnar、R. Aeschimann、T. Mallat、A. Baiker

  DOI：10.1006/jcat.1996.0234

  日期：1996.7

  to be connected with the hydration of the intermediate aldehyde (bifunctional catalysis). The influence of supported N-bases on the selectivity of Pt is a function of their chemical structure. The best results, 95% selecti-vity at 30% conversion and about 40% selectivity enhancement in the whole investigated conversion range, was obtained with Pt/C and hexamethylenetetramine. Electrochemical model studies

  已经使用分子氧和中性水溶液研究了Pt催化的C-1上未保护的1-山梨糖在C-1上氧化为2-酮-1-古洛糖酸（维生素C合成的中间体）。通过添加少量的氢氧化四烷基铵，三烷基，三芳基和脂环族胺，可以提高Pt /氧化铝和Pt / C催化剂的性能。最佳的改性剂：Pt s摩尔比为0.1左右，相当于胺与山梨糖的摩尔比为1：1700。当p K a大约为10或更高，并且这种相关性几乎不依赖于胺的化学结构。建议速率加速与中间醛的水合（双功能催化）有关。负载的N基对Pt选择性的影响是其化学结构的函数。用Pt / C和六亚甲基四胺可获得最佳结果，即在30％的转化率下95％的选择性和在整个研究的转化率范围内约40％的选择性提高。电化学模型研究表明，六亚甲基四胺吸附在Pt上，在反应过程中不会被氧化。分子模型表明，C-1处的优先氧化是由于六亚甲基四胺和山梨糖之间通过氢键形成的复合物所致。
• Effects of a New Selective Estrogen Receptor Modulator (MDL 103,323) on Cancellous and Cortical Bone in Ovariectomized Ewes: A Biochemical, Histomorphometric, and Densitometric Study
  作者：Pascale Chavassieux、Patrick Garnero、Francois Duboeuf、Philippe Vergnaud、Francoise Brunner-Ferber、Pierre D. Delmas、Pierre J. Meunier

  DOI：10.1359/jbmr.2001.16.1.89

  日期：——

  The aims of this study performed in ewes were: (1) to confirm in this animal model the effects on bone of ovariectomy (OVX) alone or associated with Lentaron (L), a potent peripheral aromatase inhibitor, used to amplify the effects of OVX and (2) to evaluate the effects of a new selective estrogen receptor modulator (SERM; MDL 103,323) on bone remodeling. Thirty‐nine old ewes were divided into five groups: sham (n = 7); OVX (n = 8); OVX + L (n = 8); OVX + L + MDL; 0.1 mg/kg per day (n = 8); and OVX + L + MDL 1 mg/kg per day (n = 8). The animals were treated for 6 months. Biochemical markers of bone turnover (urinary excretion of type 1 collagen C‐telopeptide [CTX], serum osteocalcin [OC], and bone alkaline phosphatase [BAP]) were measured each month. Bone biopsy specimens were taken at the beginning and after death at the end of the experiment. Bone mineral density (BMD) was measured by dual‐energy X‐ray absorptiometry (DXA) on the lumbar spine and femur. OVX induced a significant increase in biochemical markers. This effect was the highest after 3 months for CTX (+156% vs. sham) and after 4 months for OC and BAP (+74% and +53% vs. sham, respectively). L tended to amplify the effect of OVX on OC and BAP. OVX induced significant increases in the porosity, eroded, and osteoid surfaces in cortical bone but no effect was observed in cancellous bone. MDL treatment reduced the bone turnover as assessed by bone markers, which returned to sham levels as well as histomorphometry both in cortical and in cancellous bone. Cancellous osteoid thickness decreased by 27% (p < 0.05), mineralizing perimeter by 81% (p < 0.05), and activation frequency by 84% (p < 0.02) versus OVX + L. Femoral and spinal BMD were increased by MDL and tended to return to the sham values. The effects of OVX on bone turnover were different on cortical and cancellous bone. These effects on cortical bone were reflected by changes in biochemical markers. MDL markedly reduces bone turnover and increases BMD suggesting that this new agent may prevent postmenopausal bone loss.

  本研究在母羊中进行，旨在：(1) 在这一动物模型中确认单独或联合使用强效外周芳香化酶抑制剂Lentaron（L）的卵巢切除术（OVX）对骨骼的影响，以增强OVX的效果；(2) 评估一种新的选择性雌激素受体调节剂（SERM；MDL 103,323）对骨重建的影响。研究共纳入39只老母羊，分为五组：假手术组（n = 7）；OVX组（n = 8）；OVX + L组（n = 8）；OVX + L + MDL 0.1 mg/kg每日至（n = 8）；OVX + L + MDL 1 mg/kg每日至（n = 8）。动物治疗持续了6个月。每月测量骨代谢的生化标记物（尿中1型胶原C末端肽[CTX]、血清骨钙素[OC]和骨碱性磷酸酶[BAP]）。在实验开始时及结束时对死亡后的骨活检标本进行取样。通过双能X射线吸收法（DXA）测量腰椎和股骨的骨矿密度（BMD）。OVX显著提高了生化标记物的水平。这一效应在3个月后CTX达到最高值（+156%对比假手术组），在4个月后OC和BAP分别增加了74%和53%。L倾向于增强OVX对OC和BAP的影响。OVX使皮质骨的孔隙度、侵蚀面和骨样面显著增加，但海绵骨未观察到影响。MDL治疗降低了骨代谢，生化标记物恢复至假手术组水平，组织形态学分析显示皮质和海绵骨均如此。海绵骨骨样厚度减少了27%（p < 0.05），矿化边缘减少了81%（p < 0.05），激活频率减少了84%（p < 0.02），相较于OVX + L组。MDL使股骨和脊柱的BMD增加，并趋向恢复至假手术组水平。OVX对骨代谢的影响在皮质骨和海绵骨上有所不同。这些对皮质骨的影响体现在生化标记物的变化上。MDL显著降低了骨代谢并增加了BMD，提示该新剂可能预防绝经后骨质流失。
• Process for the production of xylitol
  申请人：——

  公开号：US20030097029A1

  公开（公告）日：2003-05-22

  The present invention relates to the production of xylitol. In particular, processes utilising L-xylose as an intermediate for xylitol production are described. The present invention also relates to process for the preparation or L-xylose, as an intermediate, by-product or end-product to be used per se.

  本发明涉及木糖醇的生产。具体描述了利用L-木糖作为木糖醇生产中间体的工艺。本发明还涉及一种用于制备L-木糖的工艺，作为中间体、副产品或最终产品的工艺。