Quebrachitol, (-)- | 484-68-4

• 物质功能分类: 生物化工 - 中草药成分
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Quebrachitol, (-)-
• 英文别名: (-)-pinitol；6-methoxycyclohexane-1,2,3,4,5-pentol；Pinitol；L-2-O-methyl-chiro-inositol；3-O-methyl-chiro-inositol；2-O-methyl-myo-inositol；1-D-4-O-METHYL-MYO-INOSITOL；D-pinitol；1D-5-O-methyl-myo-inositol；bornesitol；1D-1-O-methyl-myo-inositol；3-O-methyl-myo-inositol；D-1-methyl-myo-inositol；3-O-methyl D-inositol；(-)-D-Bornesitol；D-(-)-bornesitol
• CAS: 484-68-4；484-69-5；523-92-2；642-38-6；3559-00-0；3564-07-6；6090-97-7；7586-49-4；7600-53-5；10284-63-6；17405-65-1；22350-68-1；23887-12-9；32934-27-3；35688-46-1；56782-15-1；58769-21-4；60537-25-9；64314-40-5；74560-60-4；103773-59-7；111059-09-7；115888-70-5；144902-49-8；484-71-9
• 化学式: C₇H₁₄O₆
• 分子量: 194.185
• InChiKey: DSCFFEYYQKSRSV-AGZHHQKVSA-N

物化性质

• 熔点：
  179-185 °C (lit.)
• 比旋光度：
  56 º (c=1, H2O)
• 沸点：
  250.62°C (rough estimate)
• 密度：
  1.2501 (rough estimate)
• 溶解度：
  DMSO：125 mg/mL（643.73 mM；需要超声波）
• LogP：
  -2.119 (est)
• 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接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -3.18
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110.38
• 氢给体数：
  5.0
• 氢受体数：
  6.0

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 储存条件：
  密封储存，应存放在阴凉、干燥的库房中。

SDS

Name:	(-)-Quebrachitol 99% Material Safety Data Sheet
Synonym:	None known
CAS:	642-38-6

Section 1 - Chemical Product MSDS Name:(-)-Quebrachitol 99% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
642-38-6	(-)-Quebrachitol	97%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
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:
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.
Extinguishing Media:
Use extinguishing media most appropriate for the surrounding fire.
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.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Wash hands before eating. Use with adequate ventilation. Minimize dust generation and accumulation.
Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 642-38-6: 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: tan
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 189-192C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Slightly soluble.
Specific Gravity/Density: >1.0
Molecular Formula: C7H14O6
Molecular Weight: 194.18

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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:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 642-38-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(-)-Quebrachitol - 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# 642-38-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 642-38-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 642-38-6 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

D-松醇是D-手性肌醇的一种甲基化衍生物，具有类胰岛素作用，能够调节机体血糖平衡并缓解胰岛素抵抗，是一种新兴的降血糖功能物质。

制备

1. 从植物中提取D-松醇：D-松醇广泛存在于多种植物中。最初在松科植物中被发现，并以“松醇”命名；随后在豆科类植物中也发现了其存在且含量丰富，显著扩大了其植物来源范围。此外，D-松醇还常见于叶子花属植物、紫花苜蓿以及许多植物的花和叶中，在一些植物的汁液中也能发现该成分。在我国，大托叶云实、胡卢巴、西藏猫乳、青檀等植物种子及蜂蜜茶叶中均含有D-松醇。
2. 化学合成法：通过设计一种基于C2-对称的手性池来合成D-松醇的方法。具体步骤包括醋酸盐与甲氧基钠进行酯基转移，并在其逆反应的同时影响环氧化物的形成，诱导烯丙基环氧化物发生定向开放，最终在96%的产出中提供甲氧基乙醇；随后通过OSO4进行双羟基化反应并加入三氟乙酸制取D-松醇。这种方法能够将便宜的L-（+）-酒石酸转变为D-松醇和L-松醇。

生物活性 D-pinitol (3-O-Methyl-D-chiro-inositol) 是一种天然化合物，存在于多种植物中，如松科和豆科植物。它具有降血糖活性和心血管系统保护作用，并且还表现出抗病毒和杀幼虫活性。

体外研究 D-pinitol 能促进MCF-7细胞凋亡，通过诱导p53和Bax表达及抑制Bcl-2和NF-κB实现这一效果。

化学性质 白色结晶粉末状物质，可溶于甲醇、乙醇、DMSO等有机溶剂。主要来源于黄皮黄豆、绿皮黄豆、大豌豆、黑豆、红豆、豆角、荷兰豆及豌豆中。

用途 用于含量测定、鉴定和药理实验。具有清热利湿、消食除积、祛痰止咳的作用，能够刺激胰岛素活性并降低血糖；同时促进肌酸吸收。

总结 D-松醇作为一种新兴的降血糖功能物质，在植物提取与化学合成方面有着广泛的应用，并表现出多种生物活性和药理作用。

反应信息

• 作为反应物：
  描述：

  Quebrachitol, (-)- 在 吡啶 、 乙酸酐 、 丙酮 、 zinc(II) chloride 作用下， 生成 1D-O⁴-acetyl-O²,O³;O⁵,O⁶-diisopropylidene-O¹-methyl-myo-inositol
  参考文献：
  名称：

  647.冰片醇的结构

  摘要：

  DOI：

  10.1039/jr9580003189
• 作为产物：
  描述：

  (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one 在 palladium on activated charcoal 、 对甲苯磺酸 sodium hydroxide 、 sodium tetrahydroborate 、 cerium(III) chloride 、 R-Alpine-Hydride 、 3 A molecular sieve 、 三氟化硼乙醚 、 四丁基溴化铵 、 氢气 、 双氧水 、 sodium hydride 、 二正丁基氧化锡 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 62.67h， 生成 Quebrachitol, (-)-
  参考文献：
  名称：

  An Effective Strategy for the Synthesis of 6-O-(2-Amino-2-deoxy-.alpha.-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-Phosphate Related to Putative Insulin Mimetics

  摘要：

  Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.

  DOI：

  10.1021/jo00090a035

文献信息

• Approaches to the synthesis of glycosyl phosphatidyl inositols. Enantioselective synthesis of optically active chiro- and myo-inositols.
  作者：Carlos Jaramillo、Manuel Martin-Lomas

  DOI：10.1016/s0040-4039(00)74366-8

  日期：1991.11

  substituted D-chiro (5 and D-myo-inositol (10 derivatives has been developed starting from methyl α-D-glucopyranoside. Compounds 5 and 10 constitute valuable intermediates for the preparation of glycosyl phosphatidyl inositols.

  一种有效的合成策略，以光学活性方便地取代的D-手性（5和D-肌肌醇（10个衍生物已被开发从甲基α-d-D-吡喃葡萄糖苷起始。化合物5和10构成用于糖基磷脂酰肌醇的制备有价值的中间体。
• Bauhinia extracts
  申请人：Buchholz Herwig

  公开号：US20060188591A1

  公开（公告）日：2006-08-24

  The present invention relates to an plant extract from Bauhinia species with hypoglycemic activity, which is characterized in being obtained from a Bauhinia species and to a method for producing the extract and the use of the extract in the treatment of diabetes type 2.

  本发明涉及从羊蹄甲属植物提取的具有降血糖活性的植物提取物，其特征在于从羊蹄甲属植物中获得，并提供了一种制备该提取物的方法以及在治疗2型糖尿病中使用该提取物的用途。
• Verwendung eines Extrakts aus Bauhinia zur Herstellung kosmetischer und pharmazeutischer Zubereitungen
  申请人：MERCK PATENT GmbH

  公开号：EP1493431A2

  公开（公告）日：2005-01-05

  Die vorliegende Erfindung betrifft eine Zubereitung, enthaltend einen wässrigen oder hydroalkoholischen Extrakt aus Bauhinia, sowie die Verwendung eines wässrigen oder hydroalkoholischen Extrakts aus Bauhinia zur Herstellung einer Zubereitung zur Pflege, Konservierung oder Verbesserung des allgemeinen Zustandes der Haut oder Haare, zur Prophylaxe oder Verhinderung von Alterungsprozessen der menschlichen Haut oder menschlicher Haare und zur Prophylaxe und/oder Behandlung von Krankheiten, die mit der Alterung der Haut zusammenhängen.

  本发明涉及一种包含洋紫荆水提取物或水醇提取物的制剂，以及使用洋紫荆水提取物或水醇提取物制造一种制剂，用于护理、保存或改善皮肤或头发的一般状况，预防或防止人类皮肤或头发的老化过程，以及预防和/或治疗与皮肤老化有关的疾病。
• <b>Behavior of Esters in Liquid Hydrogen Fluoride. Facile Inversions in the Cyclitol Series</b>
  作者：E. J. Hedgley、Hewitt G. Fletcher

  DOI：10.1021/ja00878a026

  日期：1962.10
• Plouvier, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1955, vol. 241, p. 983
  作者：Plouvier

  DOI：——

  日期：——