(R)-(-)-3-羟基壬醛二甲基缩醛 | 272122-72-2

• 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: (R)-(-)-3-羟基壬醛二甲基缩醛
• 英文名称: (R)-3-hydroxynonanal dimethyl acetal
• 英文别名: (R)-1,1-bis(methoxy)-3-hydroxynonane；(3R)-1,1-dimethoxy-3-nonanol；dimethyl acetal of (R)-3-hydroxynonanal；(3R)-1,1-dimethoxynonan-3-ol
• CAS: 272122-72-2
• 化学式: C₁₁H₂₄O₃
• 分子量: 204.31
• InChiKey: GCXUFNVYAOVXOV-SNVBAGLBSA-N

物化性质

• 沸点：
  90 °C
• 密度：
  0.916
• 稳定性/保质期：

  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25

SDS

Name:	(R)-(-)-3-Hydroxynonanal Dimethyl Acetal Material Safety Data Sheet
Synonym:	None Known.
CAS:	272122-72-2

Section 1 - Chemical Product MSDS Name: (R)-(-)-3-Hydroxynonanal Dimethyl Acetal Material Safety Data Sheet
Synonym: None Known.

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
272122-72-2	(R)-(-)-3-Hydroxynonanal Dimethyl Acet	ca. 100	unlisted

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

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SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Hygroscopic (absorbs moisture from the air).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. 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.
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 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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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SECTION 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Avoid breathing dust, vapor, mist, or gas. 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 dry area. Keep refrigerated. (Store below 4C/39F.) 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# 272122-72-2: 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 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: Liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 90 - 92 deg C @ 0.7 mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 0.916
Molecular Formula: C11H24O3
Molecular Weight: 204.31

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SECTION 10 - STABILITY AND REACTIVITY
Chemical Stability:
Hygroscopic: absorbs moisture or water from the air.
Conditions to Avoid:
Exposure to moist air or water.
Incompatibilities with Other Materials:
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# 272122-72-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-(-)-3-Hydroxynonanal Dimethyl Acetal - 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# 272122-72-2: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 272122-72-2 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 272122-72-2 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 1/16/2002 Revision #2 Date: 9/18/2002 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (R)-(-)-3-羟基壬醛二甲基缩醛 在 盐酸 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 5.5h， 生成 N-(2-hydroxyethyl)-(3R)-hydroxynonanamide
  参考文献：
  名称：

  蓖麻油酸和3-羟基壬酸的手性酰胺衍生物的抗菌潜力

  摘要：

  最近已经观察到脂肪酸酰胺在药物化学中的作用越来越大。因此，使用简单快速的方法，可以得到一系列蓖麻油酸和3-羟基壬酸的手性酰胺衍生物（24种化合物），产率为31–95％。然后，评估了它们对代表革兰氏阳性和革兰氏阴性细菌，酵母菌和霉菌的13种微生物的抗菌活性。所获得的化合物显示出抗霉变的潜力。但是，测试过的霉菌种类对3-羟基壬酸衍生物的敏感性要高于从蓖麻油酸（RA）获得的酰胺。有趣的是，源自RA的异羟肟酸对白色念珠菌和热带念珠菌表现出最好的活性。。另一方面，衍生自3-羟基壬酸的异羟肟酸对其余测试微生物，尤其是对雪松假单胞菌具有最佳的抗菌潜力。所获得的衍生物可以被认为是具有潜在药理学意义的化合物，由于日益增加的微生物抗性问题，这是重要的。

  DOI：

  10.1002/aocs.12292
• 作为产物：
  描述：

  (R)-3-hydroxynonanal 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (R)-(-)-3-羟基壬醛二甲基缩醛
  参考文献：
  名称：

  Synthesis of enantiomerically pure volatile compounds derived from (R)-3-hydroxynonanal

  摘要：

  Practical preparations of enantiomerically pure R-configured 3-hydroxynonanal dimethyl acetal, 3-acetoxynonanal dimethyl acetal, methyl 3-acetoxynonanoate, delta-undecalactone, 1,3-nonanediol and its esters, 1,4-decanediol and its esters and 2-hexyltetrahydrofuran based on the ozenolysis product of commercial castor oil are described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00019-7

文献信息

• Chiral amide derivatives of ricinoleic acid and 3-hydroxynonanoic acid synthesis and cytotoxic activity
  作者：Sylwia Matysiak、Józef Kula、Alina Błaszczyk

  DOI：10.1007/s00044-019-02348-y

  日期：2019.7

  series of chiral ricinoleic and 3-hydroxynonanoic acid derivatives were synthesized in this study using various chemical and biochemical procedures. An effective method for preparation of methyl esters of 3-hydroxynonanoic acid from castor oil or methyl ricinoleate by ozonolysis and oxidation was developed. Simple, fast, and efficient procedures were applied to obtain different primary and secondary

  在这项研究中，使用各种化学和生化方法合成了一系列手性蓖麻油酸和3-羟基壬酸衍生物。提出了一种通过臭氧分解和氧化从蓖麻油或蓖麻油酸酯中制备3-羟基壬酸甲酯的有效方法。应用简单，快速和有效的程序来获得不同的伯和仲，环状和无环酰胺，包括异羟肟酸。在蓖麻油酸和3-羟基壬酸的24种合成衍生物（即甲酯，酰胺和异羟肟酸）中，首次获得并描述了16种化合物。合成的化合物对被测癌细胞具有活性，但对3-羟基壬酸衍生的异羟肟酸具有最佳的细胞毒性作用（11）对抗HeLa细胞。通常，大多数测试化合物对HT29的毒性都比HeLa癌细胞高。结果还表明，特定衍生物的（R）-和（S）-对映体的活性之间没有显着差异。
• Deuterium NMR Used To Indicate a Common Mechanism for the Biosynthesis of Ricinoleic Acid by <i>Ricinus c</i><i>ommunis</i> and <i>Claviceps </i><i>p</i><i>urpurea</i>
  作者：Isabelle Billault、Peter G. Mantle、Richard J. Robins

  DOI：10.1021/ja038814d

  日期：2004.3.1

  natural products can lead to different isotopic distributions in the product, we could expect ricinoleate isolated from castor or ergot oil to show distinct (2)H distribution patterns. To obtain information concerning the substrate and isotope effects that occur during the biosynthesis of ricinoleate, the site-specific natural deuterium distributions in methyl ricinoleate isolated from castor oil and in

  以往的研究表明，蓖麻油中的蓖麻油酸是通过油酸的直接羟基取代合成的，而有人提出蓖麻油酸是由麦角真菌 Claviceps purpurea 中的亚油酸水合形成的。蓖麻油酸合成特异性酶的机制尚未确定，但植物中脂肪酸的羟基化和去饱和显然涉及密切相关的机制。由于参与天然产物生物合成的酶的机制差异会导致产物中不同的同位素分布，我们可以预期从蓖麻油或麦角油中分离的蓖麻油酸酯显示出不同的 (2)H 分布模式。要获得有关蓖麻油酸酯生物合成过程中发生的底物和同位素效应的信息，从蓖麻油中分离出的蓖麻油酸甲酯以及从麦角油中分离出的蓖麻油酸甲酯和亚油酸甲酯中的特定位点天然氘分布已通过定量 (2) H NMR 进行了测量。首先，来自植物和真菌的蓖麻油酸甲酯的氘分布是相同的。其次，麦角亚油酸甲酯的氘分布与这种作为蓖麻油酸甲酯前体的化学物质不相容。因此，很明显，C. purpurea 中的 12-羟基化与为 R.communs
• Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXVIII. Investigation of transformations of peroxide products of olefins ozonolysis treated with hydroxylamine hydrochloride
  作者：G. Yu. Ishmuratov、A. Kh. Shayakhmetova、M. P. Yakovleva、Yu. V. Legostaeva、O. V. Shitikova、E. G. Galkin、G. A. Tolstikov

  DOI：10.1134/s1070428007080039

  日期：2007.8

  Hydroxylamine hydrochloride efficiently reduces peroxide products of olefins ozonolysis into carbonyl compounds. Depending on the substrate character, solvent, and the treatment conditions the arising aldehydes transformed along the route aldehyde -> aldoxime -> nitrile -> ester into individual compounds or their mixtures, or give the corresponding acetals.
• Synthesis of (S)-ricinoleic acid and its methyl ester with the participation of ionic liquid
  作者：Józef Kula、Radoslaw Bonikowski、Malgorzata Szewczyk、Kornelia Ciolak

  DOI：10.1016/j.chemphyslip.2014.06.005

  日期：2014.10

  (R)-Ricinoleic acid methyl ester obtained from commercial castor oil was transformed in a three-step procedure into its S-enantiomer in overall 36% yield using ionic liquid (1-butyl-3-methylimidazolium acetate) in the key step process. The developed procedure provides easy access to (S)-ricinoleic acid and its methyl ester of over 95% enantiomeric excess. Optical rotations of the newly obtained compounds as well as their chromatographic and spectral characteristics are provided and discussed in the context of enantiopurity both of the substrate material and the final products. (C) 2014 Elsevier Ireland Ltd. All rights reserved.