桃金娘烯醛 | 564-94-3

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 桃金娘烯醛
• 中文别名: 6,6-二甲基二环[3.1.1]庚-2-烯-2-甲醛；(-)-桃金娘烯醛(香桃木醛)
• 英文名称: 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
• 英文别名: myrtenal；6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxaldehyde
• CAS: 564-94-3
• 化学式: C₁₀H₁₄O
• mdl: MFCD00137969
• 分子量: 150.221
• InChiKey: KMRMUZKLFIEVAO-UHFFFAOYSA-N

物化性质

• 熔点：
  53-54 °C
• 沸点：
  220-221 °C(lit.)
• 密度：
  0.988 g/mL at 20 °C(lit.)
• 闪点：
  174 °F
• 溶解度：
  氯仿（微溶）、甲醇（微溶）
• LogP：
  2.52
• 物理描述：
  Colourless liquid; refreshing, spicy-herbaceous odour
• 折光率：
  1.496-1.507
• 保留指数：
  1187;1175;1165;1169;1170;1176;1157;1165;1172;1168;1172;1179;1165;1165;1170;1165;1170;1164;1171;1166;1176;1165;1168;1188;1168;1151.46;1155.93;1160.56;1165.32;1170.25;1175.32;1180.54;1185.89;1191.36;1196.22;1173;1171;1173;1173;1169;1155;1169;1181;1169;1181.3;1153;1163;1172;1194;1172;1165;1163;1193;1153;1172;1173;1153;1174;1197;1158;1191;1167;1172;1165;1153;1168;1196;1171;1171;1165;1178;1159;1165;1181;1192;1174;1153;1173;1178;1180;1180;1166;1166;1188;1166;1162;1166;1165;1153;1175;1182;1173;1173;1165;1170;1175;1220;1176;1171;1173;1153;1174;1175;1165;1153;1171;1169;1169;1173

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• WGK Germany：
  2
• RTECS号：
  DT5180000
• 安全说明：
  S23,S24/25
• 储存条件：
  室温

SDS

Name:	(-)-Myrtenal 98% Material Safety Data Sheet
Synonym:	Benihinal; 6,6-Dimethylbicyclo(3.1.1)hept-2-ene-2-carboxaldehyde; 2-Formyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene; Myrtenal; 2-Norpinene-2-carboxaldehyde, 6,6-dimethyl-; Bicyclo(3.1.1)hept-2-ene-2-carboxaldehyde, 6,6-dimethyl-
CAS:	564-94-3

Section 1 - Chemical Product MSDS Name:(-)-Myrtenal 98% Material Safety Data Sheet
Synonym:Benihinal; 6,6-Dimethylbicyclo(3.1.1)hept-2-ene-2-carboxaldehyde; 2-Formyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene; Myrtenal; 2-Norpinene-2-carboxaldehyde, 6,6-dimethyl-; Bicyclo(3.1.1)hept-2-ene-2-carboxaldehyde, 6,6-dimethyl-

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
564-94-3	(-)-Myrtenal	98	209-274-8

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
May cause respiratory tract irritation.
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.
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. 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. Water may be ineffective. 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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Cover with sand, dry lime or soda ash and place in a closed container for disposal. Remove all sources of ignition.
Provide ventilation.

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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. Keep container tightly closed. Avoid ingestion and inhalation. 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.

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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# 564-94-3: 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: Liquid
Color: clear very slight yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 220 - 221 deg C
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: 78 deg C ( 172.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: .9800 g/cm3
Molecular Formula: C10H14O
Molecular Weight: 150.22

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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:
Ignition sources, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 564-94-3: DT5180000 LD50/LC50:
CAS# 564-94-3: Oral, rat: LD50 = 2300 mg/kg; Skin, rabbit: LD50 = >5 gm/kg.
Carcinogenicity:
(-)-Myrtenal - 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
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# 564-94-3: No information available.
Canada
CAS# 564-94-3 is listed on Canada's DSL List.
CAS# 564-94-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 564-94-3 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

蒎烯的一种，可应用于合成OLED和制造精油等领域。

反应信息

• 作为反应物：
  描述：

  桃金娘烯醛 在 sodium triphenyl boronhydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到桃金娘烯醇
  参考文献：
  名称：

  在乙醚/甲醇/五氟苯酚溶剂体系中用硼氢化钠还原α，β-不饱和羰基化合物。N，N，N'，N'-四甲基乙二胺和1-己烯作为硼烷清除剂的用途

  摘要：

  五氟苯酚可作为有效的质子源，用于还原含甲醇的乙醚中的硼氢化钠。该系统允许以高收率将α，β-不饱和羰基化合物区域选择性还原为相应的烯丙基醇。使用1-己烯或N，N，N'，N'-四甲基乙二胺作为硼烷清除剂可适度改善该反应的区域选择性。幸运的是，原位生成的三五氟苯氧基硼氢化钠可产生α，β-不饱和羰基化合物的区域特异性1,2-还原。

  DOI：

  10.1016/0022-1139(93)05005-l
• 作为产物：
  描述：

  桃金娘烯醇 在 C₂₅H₄₃MoNO₆*H₂O 作用下， 以 水 为溶剂， 以92 %的产率得到桃金娘烯醛
  参考文献：
  名称：

  A Metallomicellar Catalyst for Controlled Oxidation of Alcohols and Lignin Mimics in Water using Open Air as Oxidant

  摘要：

  摘要 醇基和 β-O-4 (C-C) 链广泛存在于生物质原料中，它们是丰富的可再生增值化学品资源。利用露天空气作为氧化剂，以可控方式开发原料材料的直接氧化或氧化裂解的可持续方案，是生产具有重要工业价值的羰基化合物的一项具有启发性的任务。此外，将木质素氧化解聚成精细化学品近来也引起了人们的兴趣。在此，我们报告了首个催化剂系统实例，该催化剂系统可激活大气中的分子氧，在露天条件下对醇类、β-O-4（C-C）连接和水中真正的木质素等原料进行受控氧化和氧化裂解/解聚。羰基产物的选择性可通过在 ~7.0 和 ~12.0 之间改变 pH 值来控制。目前的策略突出了不使用任何外部助催化剂、氧化剂、自由基添加剂和/或破坏性有机溶剂的特点。该催化剂具有广泛的底物范围和出色的官能团耐受性。使用廉价的催化剂和易于获得的氧化剂进行多克级合成，证明了所开发方案的实用性。在一些对照实验、动力学和计算研究的帮助下，我们提出了一种合理的机制。

  DOI：

  10.1002/cssc.202301754

文献信息

• Wittig Reactions of Trialkylphosphine-derived Ylides: New Directions and Applications in Organic Synthesis
  作者：James McNulty、David McLeod、Priyabrata Das、Carlos Zepeda-Velázquez

  DOI：10.1080/10426507.2014.980907

  日期：2015.6.3

  ylides derived from short-chain trialkylphosphines in the Wittig-type olefination reactions toward the synthesis of alkenes, including stilbenes, styrenes, and 1,3-dienes, as well as reagents for homologation reactions, are described. The methods allow easy access to alkenes with high (E)-stereoselectivity in good yield. These reactions are conducted with weak bases in aqueous media, which allows easy

  图形摘要 摘要 在 Wittig 型烯化反应中，从短链三烷基膦衍生的半稳定、稳定和功能化叶立德的发展，以合成烯烃，包括二苯乙烯、苯乙烯和 1,3-二烯，以及试剂对于同系化反应，进行了描述。该方法允许以良好的收率轻松获得具有高 (E) 立体选择性的烯烃。这些反应是在水性介质中用弱碱进行的，这使得水溶性氧化膦很容易分离。还描述了用于 Wittig 反应的温和有机催化过程的发展以及在生物条件下制备报道二苯乙烯的延伸。讨论了在制备生物活性天然产物和衍生物方面的应用。
• Sulfur-controlled and rhodium-catalyzed formal (3 + 3) transannulation of thioacyl carbenes with alk-2-enals and mechanistic insights
  作者：Qiuyue Wu、Ziyang Dong、Jiaxi Xu、Zhanhui Yang

  DOI：10.1039/d1ob00116g

  日期：——

  A rhodium-catalyzed denitrogenative formal (3 + 3) transannulation of 1,2,3-thiadiazoles with alk-2-enals is achieved and a mechanistic investigation is performed, with an inverse KIE of 0.49 obtained.

  通过铑催化的1,2,3-噻二唑与烯醛的脱氮形式（3 + 3）跨环反应已实现，并进行了机理研究，获得了0.49的逆动力学同位素效应。
• A new synthesis of α,β-unsaturated aldehydes
  作者：Jean-Marc Nuzillard、Ahcene Boumendjel、Georges Massiot

  DOI：10.1016/s0040-4039(01)80653-5

  日期：1989.1

  The two carbon homologation of carbonyl compounds to α,β-unsaturated aldehydes is achieved by the Wittig-Horner reaction with N-methoxy N-methyl diethylphosphonoacetamide followed by lithium aluminum hydride reduction.

  羰基化合物与α，β-不饱和醛的两个碳同系物是通过Wittig-Horner反应与N-甲氧基N-甲基二乙基膦酰基乙酰胺，然后氢化铝锂还原而实现的。
• Pharmaceutical Compositions Comprising Deuterium-Enriched Perillyl Alcohol, Iso-Perillyl Alcohol and Derivatives Thereof
  申请人：NEONC TECHNOLOGIES INC.

  公开号：US20160039731A1

  公开（公告）日：2016-02-11

  The present invention, provides for a deuterium-enriched monoterpene or sesquiterpene such as perillyl alcohol, or a deuterium-enriched isomer or analog of monoterpenes or sesquiterpenes, such as isoperillyl alcohol. The present invention also provides for a deuterium-enriched derivative of a monoterpene or sesquiterpene, such as a perillyl alcohol carbamate or a deuterium-enriched derivative of an isomer or analog of a monoterpene or sesquiterpene, such as an isoperillyl alcohol carbamate. The deuterium-enriched derivative may be perillyl alcohol or isoperillyl alcohol conjugated with a therapeutic agent such as a chemotherapeutic agent. The present invention also provides for a method of treating a disease such as cancer, comprising the step of delivering to a patient a therapeutically effective amount of a deuterium-enriched compound.

  本发明提供了一种氘增强的单萜或倍半萜，例如桃金娘醇，或者一种氘增强的单萜或倍半萜的同系物或类似物，例如异桃金娘醇。本发明还提供了一种单萜或倍半萜的氘增强衍生物，例如桃金娘醇碳酰胺或一种单萜或倍半萜的同系物或类似物的氘增强衍生物，例如异桃金娘醇碳酰胺。所述氘增强衍生物可以是与治疗剂如化疗剂结合的桃金娘醇或异桃金娘醇。本发明还提供了一种治疗疾病如癌症的方法，包括向患者提供治疗有效量的氘增强化合物。
• [EN] METHODS AND DEVICES FOR USING ISOPERILLYL ALCOHOL<br/>[FR] PROCÉDÉS ET DISPOSITIFS POUR L'UTILISATION D'ALCOOL ISOPERILLYLIQUE
  申请人：NEO ONCOLOGY INC

  公开号：WO2012083178A1

  公开（公告）日：2012-06-21

  The present invention provides for a method of treating a disease such as cancer, comprising the step of administering to a patient a therapeutically effective amount of an isomer or analog of monoterpene or sesquiterpene (or its derivative), such as an isoperillyl alcohol. The present invention also provides for a method of treating a disease comprising the step of administering to a patient a therapeutically effective amount of a derivative of an isomer or analog of monoterpene or sesquiterpene, such as an isoperillyl alcohol carbamate. The derivative may be an isoperillyl alcohol conjugated with a therapeutic agent such as a chemotherapeutic agent. The route of administration may vary, including inhalation, intranasal, oral, transdermal, intravenous, subcutaneous or intramuscular injection.

  本发明提供了一种治疗疾病的方法，包括向患者施用单萜或倍半萜的异构体或类似物（或其衍生物）的治疗有效量，例如异壬醇。本发明还提供了一种治疗疾病的方法，包括向患者施用单萜或倍半萜的异构体或类似物的衍生物的治疗有效量，例如异壬醇氨基甲酸酯。该衍生物可以是与化疗药物等治疗剂结合的异壬醇。给药途径可以有所不同，包括吸入、鼻内、口服、经皮、静脉、皮下或肌肉注射。

表征谱图