(R)-氧化柠檬烯 | 1195-92-2

• 物质功能分类: 化学试剂 - 有机试剂 - 环氧化物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 中文名称: (R)-氧化柠檬烯
• 中文别名: (+)-氧化柠檬烯；1,8-萜二烯单氧化物；柠檬烯-1,2-环氧化物；1-甲基-4-(1-甲基乙烯基)-7-氧杂二环[4.1.10]-庚烷
• 英文名称: Limonene oxide
• 英文别名: limonene 1,2-epoxide；1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
• CAS: 1195-92-2
• 化学式: C₁₀H₁₆O
• mdl: MFCD00005127
• 分子量: 152.236
• InChiKey: CCEFMUBVSUDRLG-UHFFFAOYSA-N

物化性质

• 沸点：
  113-114 °C50 mm Hg(lit.)
• 密度：
  0.929 g/mL at 25 °C(lit.)
• 闪点：
  150 °F
• LogP：
  2.43
• 物理描述：
  Liquid
• 溶解度：
  Practically insoluble to insoluble in water
• 折光率：
  1.464-1.474
• 保留指数：
  1139;1120;1119;1148;1117;1119;1113;1117;1164;1128.8;1133;1122;1148;1119;1122;1116;1108;1119;1116;1116;1127;1116;1120;1120;1118;1122;1123;1100;1098;1127;1144;1118;1114;1118;1119;1126;1121;1115;1125;1120;1122;1123;1123;1137;1138;1126;1118;1118;1122;1123;1121;1121;1127;1121;1120;1120;1120;1122;1125;1125;1109;1146;1106;1129;1123;1112;1127;1112;1121;1121;1125;1122;1125;1124;1126;1125;1123;1133;1125;1125;1125;1129;1125;1125
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，没有已知的危险反应。请避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

毒理性

• 副作用

神经毒素 - 其他中枢神经系统神经毒素

Neurotoxin - Other CNS neurotoxin

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 毒性数据

LC50（大鼠）= 60,000 毫克/立方米

LC50 (rat) = 60,000 mg/m3

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• WGK Germany：
  3
• 安全说明：
  S24/25
• 危险性防范说明：
  P210,P264,P270,P280,P301+P312,P330,P370+P378,P403+P235,P501
• 危险性描述：
  H302,H227
• 储存条件：
  请将贮藏器保持密封状态，并存放在阴凉、干燥的地方。同时，确保工作环境中具有良好的通风或排气设施。

SDS

Name:	(+)-Limonene oxide 97% cis/trans mixture Material Safety Data Sheet
Synonym:	1-Methyl-4-(1-methylethenyl)-7-oxabicyclo(4.1.0)heptane; 1-Methyl-4-(1-methylvinyl)-7-oxabicyclo[4.1.0]heptane; 7-Oxabicyclo(4.1.0)heptane, 1-methyl-4-(1-methylethenyl)-; 7-Oxabicyclo[4.1.0]heptane, 1-methyl-4-(1-methylethenyl)-; Bicyclo[4
CAS:	1195-92-2

Section 1 - Chemical Product MSDS Name:(+)-Limonene oxide 97% cis/trans mixture Material Safety Data Sheet
Synonym:1-Methyl-4-(1-methylethenyl)-7-oxabicyclo(4.1.0)heptane; 1-Methyl-4-(1-methylvinyl)-7-oxabicyclo[4.1.0]heptane; 7-Oxabicyclo(4.1.0)heptane, 1-methyl-4-(1-methylethenyl)-; 7-Oxabicyclo[4.1.0]heptane, 1-methyl-4-(1-methylethenyl)-; Bicyclo[4

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1195-92-2	(+)-Limonene oxide, mixture of cis and	97	214-805-1

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. May cause chemical conjunctivitis and corneal damage.
Skin:
May cause irritation and dermatitis. May cause cyanosis of the extremities.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. 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. Aspiration may lead to pulmonary edema. Inhalation at high concentrations may cause CNS depression and asphixiation.
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. Use water spray to keep fire-exposed containers cool. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated. Combustible liquid and vapor.
Extinguishing Media:
Use water spray to cool fire-exposed containers. 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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Use a spark-proof tool. 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 only in a well-ventilated area. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Avoid ingestion and inhalation. Do not allow contact with water. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Keep from contact with moist air and steam. Keep away from heat and flame.
Storage:
Keep away from sources of ignition. 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 general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 1195-92-2: 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 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: Clear liquid
Color: clear, colorless
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 113.0 - 114.0 deg C @ 50.00mm
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: 65 deg C ( 149.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: .9290g/cm3
Molecular Formula: C10H16O
Molecular Weight: 152.24

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1195-92-2: RN8761000 LD50/LC50:
CAS# 1195-92-2: Inhalation, rat: LC50 = 60000 mg/m3; Oral, mouse: LD50 = 2700 uL/kg; Oral, rat: LD50 = 3.8 mL/kg.
Carcinogenicity:
(+)-Limonene oxide, mixture of cis and trans - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 1195-92-2: 1
Canada
CAS# 1195-92-2 is listed on Canada's DSL List.
CAS# 1195-92-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1195-92-2 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：香水

反应信息

• 作为反应物：
  描述：

  (R)-氧化柠檬烯 在 copper(I) bromide 作用下， 以85%的产率得到3-异丙基-6-甲基-2-环己烯-1-酮
  参考文献：
  名称：

  用环氧柠檬烯合成香芹酚的方法

  摘要：

  本发明提供了用环氧柠檬烯合成香芹酚的方法，包括以下步骤：步骤一，环氧柠檬烯在路易斯酸类催化剂A的作用下，加热发生开环重排反应，生成异二氢香芹酮，反应结束后，向反应液中加入白油，减压精馏得到异二氢香芹酮成品，催化剂A留在釜液中；步骤二，将步骤一制得的异二氢香芹酮和催化剂B溶于溶剂，加热发生脱氢氧化反应，生成香芹酚，反应过程中通过气相色谱监测，当异二氢香芹酮含量剩下30%‑40%时终止反应，过滤分离催化剂B，滤液减压精馏，回收没有反应的异二氢香芹酮、溶剂，进一步精馏得到香芹酚成品。本发明的原料廉价易得，合成工艺绿色环保，催化剂可循环使用，适合工业化生产。

  公开号：

  CN105481657B
• 作为产物：
  描述：

  2-bromo-1-methyl-4-(prop-1-en-2-yl)cyclohexanol 在 二乙胺 作用下， 反应 2.0h， 以87%的产率得到(R)-氧化柠檬烯
  参考文献：
  名称：

  天然萜烯的催化 β-溴羟基化：合成萜烯环氧化物的有用中间体

  摘要：

  在一步法中，从天然萜烯中合成了各种 β-溴醇，收率很好。使用不同的催化剂，反应在室温下进行，H2O 作为亲核试剂，N-溴代琥珀酰亚胺作为溴源，在温和的反应条件下进行。随后合成的β-溴醇以良好的产率原位转化为相应的环氧化物。

  DOI：

  10.1155/2019/9268567
• 作为试剂：
  描述：

  香芹醇 在 (R)-氧化柠檬烯 、 palladium 10% on activated carbon 作用下， 反应 2.0h， 以99%的产率得到香芹酚
  参考文献：
  名称：

  一种以柠檬烯环氧化物为加氢受体的香芹酚制备方法

  摘要：

  本发明公开了一种以柠檬烯环氧化物为加氢受体的香芹酚制备方法，属于精细化工领域。该方法以香芹醇作为原料合成香芹酚，添加柠檬烯环氧化物为加氢受体。优点在于：柠檬烯环氧化物可以将反应产生的活性氢及时消耗，避免氢气的生成，反应在常压下进行，提高了反应的安全性，且促进脱氢反应正向移动从而提高产品收率；反应时间短，工艺简单；负载型钯碳催化剂可重复使用，实现绿色工业化生产。

  公开号：

  CN113185383B

文献信息

• 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane: An efficient and high oxygen content oxidant in various oxidative reactions
  作者：Kaveh Khosravi、Shirin Naserifar

  DOI：10.1016/j.tet.2018.09.041

  日期：2018.11

  Several oxidative approaches namely thiocyanation of aromatic compounds, epoxidation of alkenes, amidation of aromatic aldehydes, epoxidation of α, β-unsaturated ketones, oxidation of sulfides to sulfoxides and sulfones, bayer-villeger reaction, bromination and iodation of aniline and phenol derivatives oxidative esterification, oxidation of pyridines and oxidation of secondary, allylic and benzyllic

  几种氧化方法分别是芳族化合物的硫氰化，烯烃的环氧化，芳族醛的酰胺化，α，β-不饱和酮的环氧化，硫化物氧化为亚砜和砜，拜耳-维格反应，苯胺和苯酚衍生物的溴化和碘化氧化酯化，吡啶氧化和仲，烯丙基和苄基醇的氧化反应均使用1,1,2,2-四氢过氧-1,2-二苯乙烷作为潜在的固体氧化剂进行，可储存数月而不会损失其活性。所有步骤均通过温和的反应条件完成，并以高收率和较短的反应时间提供了产物。
• A polyhedral oligomeric silsesquioxane (POSS)-bridged oxo-molybdenum Schiff base complex with enhanced heterogeneous catalytic activity in epoxidation
  作者：Yan Leng、Jian Liu、Chenjun Zhang、Pingping Jiang

  DOI：10.1039/c3cy01014g

  日期：——

  We have generated a new heterogeneous catalyst by bridging an oxo-molybdenum Schiff base on a polyhedral oligomeric silsesquioxane (POSS) via covalent attachment. The resulting POSS-bridged oxo-molybdenum Schiff base complex catalyst was fully characterized by 1H NMR, XRD, FT-IR, SEM, TGA, and contact angle analysis, and its catalytic potential was studied for the epoxidation of alkenes using aqueous

  我们通过共价连接将多面体低聚倍半硅氧烷（POSS）上的氧钼席夫碱桥接，从而产生了一种新的非均相催化剂。通过1 H NMR，XRD，FT-IR，SEM，TGA和接触角分析对得到的POSS桥联的氧钼席夫碱络合物催化剂进行了充分表征，并研究了其催化潜力用于叔丁基醚水溶液的环氧化丁基过氧化氢（TBHP）作为氧化剂。发现该催化剂比相应的均相类似物高效且显示出更高的催化反应性，并具有容易回收和再循环非均相催化剂的额外益处。POSS桥联的氧钼希夫碱复合物成功地重复使用了四次，而活性没有明显损失。揭示了独特的三维网络催化剂结构和催化剂中POSS单元的疏水性，是造成催化剂在环氧化反应中优异性能的原因。
• Liquid‐phase oxidation of olefins with rare hydronium ion salt of dinuclear dioxido‐vanadium(V) complexes and comparative catalytic studies with analogous copper complexes
  作者：Abhishek Maurya、Chanchal Haldar

  DOI：10.1002/aoc.6203

  日期：2021.6

  [NsalLH4], respectively). Anionic vanadium and copper complexes 1, 2, 3, and 4 were isolated in the form of their hydronium ion salt, which is rare. The molecular structure of the hydronium ion salt of anionic dinuclear vanadium dioxido complex [(VO2)2(salLH)]− (1) was established through single‐crystal X‐ray analysis. The chemical and structural properties were studied using Fourier transform infrared

  使用多种芳族和脂族烯烃的均相液相氧化检查双核阴离子钒二氧化配合物[（VO 2）2（SAL LH）] - （1）和[（VO 2）2（Nsal LH）] - （2）和双核铜络合物[（CuCl）2（sal LH）] -（3）和[（CuCl）2（Nsal LH）] -（4）（碳酰肼与水杨醛和4-二乙基氨基水杨醛的反应分别得到席夫碱配体[ sal LH 4 ]和[ Nsal LH 4 ]）。阴离子钒和铜配合物1，2，3，和4在它们的水合氢离子的盐的形式，这是罕见的分离。阴离子双核钒二氧化物络合物[（VO 2）2（sal LH）] -（1的水合氢离子盐的分子结构）是通过单晶X射线分析确定的。使用傅立叶变换红外（FT-IR），紫外可见光（UV-Vis），1 H和13 C核磁共振（NMR），电喷雾电离质谱（ESI-MS），顺磁性电子对化学和结构性质进行了研究共振（EPR）光谱和热重分析（TGA）。在过氧化
• Oxidation Reactions Using Magnesium Monoperphthalate: A Comparison with<i>m</i>-Chloroperoxybenzoic Acid
  作者：Paul Brougham、Mark S. Cooper、David A. Cummerson、Harry Heaney、Nicola Thompson

  DOI：10.1055/s-1987-28153

  日期：——

  Magnesium monoperphthalate hexahydrate (MMPP), a newly developed reagent with high stability at ambient temperatures, has been shown to oxidise a wide range of substrates under mild conditions: the substrates include alkenes, ketones. sulphides and sulphoxides, pyridine, and dipotassium p-tolylpentafluorosilicate.

  六水合单过邻苯二甲酸镁（MMPP）是一种新开发的试剂，具有在室温下高度稳定的特性，已被证明能在温和条件下氧化多种底物，包括烯烃、酮、硫化物、亚砜、吡啶和二钾对甲苯基五氟硅酸盐。
• [EN] PEPTIDOMIMETICS FOR THE TREATMENT OF CORONAVIRUS AND PICORNAVIRUS INFECTIONS<br/>[FR] PEPTIDOMIMÉTIQUES POUR LE TRAITEMENT D'INFECTIONS PAR CORONAVIRUS ET PICORNAVIRUS
  申请人：UNIV EMORY

  公开号：WO2020247665A1

  公开（公告）日：2020-12-10

  Compounds, compositions and methods for preventing, treating or curing a coronavirus, picornavirus, and/or Hepeviridae virus infection in human subjects or other animal hosts. Specific viruses that can be treated include enteroviruses. In one embodiment, the compounds can be used to treat an infection with a severe acute respiratory syndrome virus, such as human coronavirus 229E, SARS, MERS, SARS-CoV-1 (OC43), and SARS-CoV- 2. In another embodiment, the methods are used to treat a patient co-infected with two or more of these viruses, or a combination of one or more of these viruses and norovirus.

  用于预防、治疗或治愈人类主体或其他动物宿主中的冠状病毒、小RNA病毒和/或肝炎病毒感染的化合物、组合物和方法。可治疗的特定病毒包括肠病毒。在一个实施例中，这些化合物可用于治疗严重急性呼吸综合征病毒感染，如人类冠状病毒229E、SARS、MERS、SARS-CoV-1（OC43）和SARS-CoV-2。在另一个实施例中，这些方法用于治疗患有两种或更多这些病毒的患者，或一种或多种这些病毒与诺如病毒的组合。

表征谱图