1-O-月桂酰-beta-D-吡喃葡萄糖 | 64395-92-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 1-O-月桂酰-beta-D-吡喃葡萄糖
• 英文名称: 1-O-lauroyl-β-D-glucopyranose
• 英文别名: 1-O-lauroyl-β-glucopyranose；1β-Lauroyl-D-glucopyranose；1-Oxododecyl b-D-glucopyranoside；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dodecanoate
• CAS: 64395-92-2
• 化学式: C₁₈H₃₄O₇
• 分子量: 362.464
• InChiKey: HABWUWJGNVZVPU-LHKMKVQPSA-N

物化性质

• 熔点：
  124°C
• 沸点：
  414.06°C (rough estimate)
• 密度：
  1.1130 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

SDS

Name:	1-Oxododecyl-beta-D-glucopyranoside 99+% Material Safety Data Sheet
Synonym:	None
CAS:	64395-92-2

Section 1 - Chemical Product MSDS Name:1-Oxododecyl-beta-D-glucopyranoside 99+% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
64395-92-2	1-Oxododecyl-beta-D-glucopyranoside	>99	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.
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. Runoff from fire control or dilution water may cause pollution.
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. Remove contaminated clothing and wash before reuse. 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:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. 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# 64395-92-2: 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 minimize contact with skin.
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: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 124 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: C18H34O7
Molecular Weight: 362.45

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation, moisture.
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# 64395-92-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-Oxododecyl-beta-D-glucopyranoside - 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# 64395-92-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 64395-92-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 64395-92-2 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：

  2-Deoxy-D-glucose 、 1-O-月桂酰-beta-D-吡喃葡萄糖 在 Lycopersicon pennellii 作用下， 以 various solvent(s) 为溶剂， 反应 6.0h， 生成 1-O-lauroyl-2-deoxy-β-glucopyranose
  参考文献：
  名称：

  A survey of the nature of glucose acylation reactions in plant extracts

  摘要：

  A variety of plant species have been shown to catalyse anomeric acyl exchange from a number of 1-O-fatty-acyl-beta-glucoses as donor substrates to [(14)C]-glucose as an acceptor. The activity in wild tomato Lycopersicon penneliii has been analysed in detail by using analogs of glucose as accepters and a number of 1-O-acyl-beta-glucoses and 1-O-acyl-2-deoxyglucoses as acyl donors. Compared to 1-O-isobutyryl-beta-glucose, the analogous 1-O-isobutyryl-beta-2-deoxyglucose is an effective donor both to glucose (ca. 75%) and to 2-deoxyglucose (ca. 95%). On the contrary, compared to 1-O-isobutyryl-beta-glucose, 1-O-isobutyryl-alpha-2-deoxyglucose is a poor donor both to glucose (ca. 4%) and to deoxyglucose (ca. 6%). The glucose analogs free at the anomeric center such as 3-O-methylglucose and 2-deoxyglucose are competent acyl accepters from various 1-O-acyl-beta-glucoses whereas 1-O-methylglucose is not. The primary initial product of acyl transfer from 1-O-isobutyryl-beta-glucose to [(14)C]-glucose is beta-glucosidase-cleavable 1-O-acyl-[(14)C]-beta-glucose, whereas the isobutyryl-[(14)C]-3-O-methylglucose generated from 1-O-isobutyryl-beta-glucose and [(14)C]-3-O-methylglucose is beta-glucosidase-resistant. The transfer of the acyl group to 3-O-methylglucose occurs at the anomeric center; therefore the resistance to beta-glucosidase reflects the strict specificity of beta-glucosidase for glucose. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00319-2
• 作为产物：
  描述：

  月桂酰氯 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 6.0h， 生成 1-O-月桂酰-beta-D-吡喃葡萄糖
  参考文献：
  名称：

  无糖化学保护组织-I-乳糖，麦芽糖和葡萄糖的酯化区域选择性羟基异头异构体

  摘要：

  酰基氯的治疗与巯基噻唑，巯基-苯并噻唑，硝基苯酚和在的Et存在下8-羟基喹啉3 N，在相应的反应性酰胺，得到高产率- ，-thioesters -和芳基酯-和-分别。酯- ，-和-在吡啶过量β乳糖反应，得到相应的β-酯，-由糖的异头羟基的酯化得到的。酰胺，-给了α-乳糖酯，- 。酰胺和酯，，反应与β-麦芽糖，从而得到相应的β-麦芽糖酯，，，而化合物-反应，与β葡萄糖，得到相应的β葡糖酯- 。这似乎是已知糖的极少数选择性化学修饰之一，其不涉及繁琐的保护-去保护方法。现在市售的麦芽糖基和葡萄糖基酯和–是新型的非离子型水溶性洗涤剂，可用于研究细胞膜蛋白。

  DOI：

  10.1016/0040-4020(86)80009-6

文献信息

• US6011145A
  申请人：——

  公开号：US6011145A

  公开（公告）日：2000-01-04
• A survey of the nature of glucose acylation reactions in plant extracts
  作者：Gurdev S. Ghangas

  DOI：10.1016/s0031-9422(99)00319-2

  日期：1999.11

  A variety of plant species have been shown to catalyse anomeric acyl exchange from a number of 1-O-fatty-acyl-beta-glucoses as donor substrates to [(14)C]-glucose as an acceptor. The activity in wild tomato Lycopersicon penneliii has been analysed in detail by using analogs of glucose as accepters and a number of 1-O-acyl-beta-glucoses and 1-O-acyl-2-deoxyglucoses as acyl donors. Compared to 1-O-isobutyryl-beta-glucose, the analogous 1-O-isobutyryl-beta-2-deoxyglucose is an effective donor both to glucose (ca. 75%) and to 2-deoxyglucose (ca. 95%). On the contrary, compared to 1-O-isobutyryl-beta-glucose, 1-O-isobutyryl-alpha-2-deoxyglucose is a poor donor both to glucose (ca. 4%) and to deoxyglucose (ca. 6%). The glucose analogs free at the anomeric center such as 3-O-methylglucose and 2-deoxyglucose are competent acyl accepters from various 1-O-acyl-beta-glucoses whereas 1-O-methylglucose is not. The primary initial product of acyl transfer from 1-O-isobutyryl-beta-glucose to [(14)C]-glucose is beta-glucosidase-cleavable 1-O-acyl-[(14)C]-beta-glucose, whereas the isobutyryl-[(14)C]-3-O-methylglucose generated from 1-O-isobutyryl-beta-glucose and [(14)C]-3-O-methylglucose is beta-glucosidase-resistant. The transfer of the acyl group to 3-O-methylglucose occurs at the anomeric center; therefore the resistance to beta-glucosidase reflects the strict specificity of beta-glucosidase for glucose. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Chimie des sucres sans groupements protecteurs - I - esterification regioselective de l'hydroxyle anomere du lactose, du maltose et du glucose
  作者：Daniel Plusquellec、Fabienne Roulleau、Francoise Bertho、Martine Lefeuvre、Eric Brown

  DOI：10.1016/0040-4020(86)80009-6

  日期：1986.1

  Et3N, afforded high yields of the corresponding reactive amides –, -thioesters – and aryl esters – and –, respectively. The esters -, - and – reacted with excess β-lactose in pyridine, to give the corresponding β-esters, – resulting from esterification of the anomeric hydroxyl of the sugar. The amides , – gave the α-lactosyl esters ,–. The amide and the esters ,, reacted with β-maltose, thus affording

  酰基氯的治疗与巯基噻唑，巯基-苯并噻唑，硝基苯酚和在的Et存在下8-羟基喹啉3 N，在相应的反应性酰胺，得到高产率- ，-thioesters -和芳基酯-和-分别。酯- ，-和-在吡啶过量β乳糖反应，得到相应的β-酯，-由糖的异头羟基的酯化得到的。酰胺，-给了α-乳糖酯，- 。酰胺和酯，，反应与β-麦芽糖，从而得到相应的β-麦芽糖酯，，，而化合物-反应，与β葡萄糖，得到相应的β葡糖酯- 。这似乎是已知糖的极少数选择性化学修饰之一，其不涉及繁琐的保护-去保护方法。现在市售的麦芽糖基和葡萄糖基酯和–是新型的非离子型水溶性洗涤剂，可用于研究细胞膜蛋白。