桃金娘烯醇 | 515-00-4

• 物质功能分类: 原料药 - 呼吸系统用药 - 祛痰药
• 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: 桃金娘烯醇
• 中文别名: 6,6-二甲基二环[3.1.1]庚-2-烯-2-甲醇
• 英文名称: myrtenol
• 英文别名: (6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methanol；2-pinen-10-ol；6,6-dimethyl-bicyclo[3.1.1]hept-2-ene-2-methanol；6,6-dimethyl-2-oxymethyl-bicyclo[3.1.1]hept-2-ene；(6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl)methanol
• CAS: 515-00-4
• 化学式: C₁₀H₁₆O
• mdl: MFCD00137970
• 分子量: 152.236
• InChiKey: RXBQNMWIQKOSCS-UHFFFAOYSA-N

物化性质

• 沸点：
  221-222 °C(lit.)
• 密度：
  0.954 g/mL at 25 °C(lit.)
• 闪点：
  89 °C
• 溶解度：
  Insoluble in water, soluble in alcohol and oils, not in Propylene glycol.
• LogP：
  3.22
• 物理描述：
  Colourless or pale straw-coloured liquid; Warm-herbaceous, slightly woody and discretely medicinal-camphoraceous odour of moderate to poor tenacity
• 折光率：
  1.490-1.500
• 保留指数：
  1212.8;1198;1204;1193;1196;1237;1202;1192;1195;1202.9;1193;1196;1196;1194;1194;1196;1194;1194;1195;1242;1214;1199.4;1201.3;1202.1;1191;1195;1194;1193;1194;1203;1195;1194;1198;1197;1218;1202;1194;1194;1196;1196;1196;1160;1194;1199;1194;1204;1196;1194;1194;1206;1206;1192;1193;1191;1191;1191;1191;1198;1187;1189;1193;1182;1189;1194;1195;1194;1191;1194;1191;1191;1195;1194;1206;1201;1191;1193;1194;1190;1152;1191;1201;1194;1208;1197;1207;1191;1196;1202;1209;1214;1196;1200;1202;1195;1199;1192;1201;1201;1196;1206;1195;1194;1194;1196;1207;1196;1191;1194;1196;1196;1190;1197;1170;1198;1198;1200;1197;1170;1196;1194;1196;1192;1196;1195.1;1169;1170;1198;1194;1208;1181;1181;1196;1198;1194;1198;1198;1196;1194;1196;1196;1194;1195;1197;1198;1195;1193;1188;1202;1202;1196;1200;1195;1200;1194;1193;1216;1197;1165;1192;1196;1203;1198;1195;1212;1176;1199;1191;1195;1196;1203;1196;1194;1224;1194;1179;1194;1197;1194;1195;1194;1194;1194;1178;1179;1194;1194;1193;1194;1188.3;1194;1201;1189;1198;1194;1196;1195;1194;1195;1150;1194;1194;1191;1192;1191
• 稳定性/保质期：
  1. 按照规格使用和贮存，不会发生分解，避免与氧化物接触。 2. 存在于烤烟烟叶中。 3. 以游离态和乙酸酯的形式存在于桉树油和桃金娘油中。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2906199090
• 储存条件：
  储存于阴凉、干燥、通风良好的库房中。远离火种和热源，并防止阳光直射。包装需密封保存。与酸类及食用化学品分开存放，切忌混储。存储区域应备有合适的材料以处理泄漏物。

SDS

Name:	(-)-Myrtenol 97+% Material Safety Data Sheet
Synonym:	(-)-Pin-2-ene-10-ol; Bicyclo[3.1.1]hept-2-ene-, 6,6-dimethyl-2-(hydroxymethyl)-; Bicyclo[3.1.1]hept-2-ene-2-methanol, 6,6-dimethyl-
CAS:	515-00-4

Section 1 - Chemical Product MSDS Name:(-)-Myrtenol 97+% Material Safety Data Sheet
Synonym:(-)-Pin-2-ene-10-ol; Bicyclo[3.1.1]hept-2-ene-, 6,6-dimethyl-2-(hydroxymethyl)-; Bicyclo[3.1.1]hept-2-ene-2-methanol, 6,6-dimethyl-

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
515-00-4	(-)-Myrtenol	>97	208-193-5

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

---

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. 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.

---

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:

---

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 agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

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.

---

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.

---

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# 515-00-4: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Clear liquid
Color: clear, colorless
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: viscous
Boiling Point: 221 - 222 deg C
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: 89 deg C ( 192.20 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: .9820 g/cm3
Molecular Formula: C10H16O
Molecular Weight: 152.24

---

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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 515-00-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(-)-Myrtenol - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

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.

---

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# 515-00-4: No information available.
Canada
CAS# 515-00-4 is listed on Canada's DSL List.
CAS# 515-00-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 515-00-4 is listed on the TSCA inventory.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

桃金娘烯醇 简介

桃金娘烯醇存在于精油中。它能抑制粘液分泌、减少粘液沉积并改变其粘弹性，具有良好的祛痰作用，可用于治疗呼吸道疾病，是一种重要的医药原料。此外，桃金娘烯醇作为一种广泛用途的香料，并且是重要的精细化工中间体，可以进一步合成如紫苏醛和紫苏葶等更高级的香料。

理化性质

桃金娘烯醇以游离态和乙酸酯的形式存在于桉树油和桃金娘油中。它具有草香、木香和樟脑样的香气，其乙酸酯则散发愉快清新草香。为无色液体，沸点在221～224℃（101kPa），相对密度约为0.978，折射率为1.496。由β-蒎烯经环氧化后再催化异构取得，可用于薰衣草、柑橘型香精。通过将β-蒎烯氯化、成酯、水解制取桃金娘烯醇，再进行选择性氧化可合成桃金娘烯醛（Myrtenal）。桃金娘烯醛是一种广泛用途的香料，并且是重要的精细化工中间体，可用于合成如甜味剂紫苏葶等。

应用

桃金娘烯醇作为一种重要的双环单萜烯醇，具有檀木香和清凉薄荷香，香气柔和。作为食用香料，它可用于可乐、薰衣草和柑橘型香精中，是优良的和合剂与修饰剂；此外，桃金娘烯醇还可用作杀虫剂。其乙酸酯散发愉快而清新的草香，能很好地与其他精油如迷迭香、香紫苏、薰衣草等和合。以桃金娘烯醇为主要成分的标准桃金娘油具有突出的净化功能，温和不刺激，并有明显的杀菌效果，良好的收敛作用，常被添加于皮肤保养产品。

在医药工业中，桃金娘烯醇适用于急性和慢性鼻炎及鼻窦炎、气管炎和支气管炎等疾病的治疗，尤其在鼻功能手术后的术后治疗和支气管扩张、慢性阻塞性肺病方面效果显著。作为反应中间体，桃金娘烯醇可用于合成桃金娘烯醛、紫苏醇、紫苏醛和紫苏葶等精细化学品。

食品添加剂最大允许使用量与残留量标准

• 添加剂中文名称：桃金娘烯醇
• 允许使用该种添加剂的食品中文名称：所有食品均可
• 添加剂功能：食品用香料，用于配制香精的各香料成分不得超过在GB 2760中的最大允许使用量和最大允许残留量

生产方法包括：

1. 烟草：FC，18。
2. 将β-蒎烯氯化、成酯、水解制取桃金娘烯醇。
3. 光敏氧化后还原得到桃金娘烯醇。
4. β-蒎烯环氧化反应后再异构化，是合成通用方法。

反应信息

• 作为反应物：
  描述：

  桃金娘烯醇 在 ortho-tungstic acid 十二/十四烷基二甲基氧化胺 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 以85%的产率得到myrtenol epoxide
  参考文献：
  名称：

  钨酸在缓冲介质中用30％过氧化氢对烯丙基和均烯丙基醇进行立体选择性氧化

  摘要：

  钨酸催化的烯丙醇过氧化氢环氧化可提供与VO（acac）2 / tBuOOH体系相同的主要非对映异构体，且具有相当的立体选择性。相反，均烯丙基醇的环氧化似乎立体选择性低得多。

  DOI：

  10.1016/s0040-4039(00)84080-0
• 作为产物：
  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

文献信息

• DERMATOLOGICAL COMPOSITIONS AND METHODS
  申请人：——

  公开号：US20020141952A1

  公开（公告）日：2002-10-03

  Disclosed are methods and compositions for regulating the melanin content of mammalian melanocytes; regulating pigmentation in mammalian skin, hair, wool or fur; treating or preventing various skin and proliferative disorders; by administration of various compounds, including alcohols, diols and/or triols and their analogues.

  公开了用于调节哺乳动物黑素细胞的黑色素含量的方法及组合物；通过施用包括醇、二醇和/或三醇及其类似物在内的各种化合物，来调节哺乳动物皮肤、毛发、羊毛或毛皮的色素沉着；以及治疗或预防各种皮肤和增殖性障碍。
• 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。
• Unique catalysis of gold nanoparticles in the chemoselective hydrogenolysis with H2: cooperative effect between small gold nanoparticles and a basic support
  作者：Akifumi Noujima、Takato Mitsudome、Tomoo Mizugaki、Koichiro Jitsukawa、Kiyotomi Kaneda

  DOI：10.1039/c2cc32850j

  日期：——

  Gold nanoparticles on hydrotalcite act as a heterogeneous catalyst for the chemoselective hydrogenolysis of various allylic carbonates to the corresponding terminal alkenes using H2 as a clean reductant. The combination of gold nanoparticles and basic supports elicited significantly unique and selective catalysis in the hydrogenolysis.

  金纳米颗粒在水滑石上作为异质催化剂，用于选择性氢解各种烯丙基碳酸盐，生成相应的末端烯烃，以H2作为清洁还原剂。金纳米颗粒与碱性载体的结合显著引发了独特的选择性氢解催化作用。
• Cosmetic compositions
  申请人：Symrise AG

  公开号：EP2745878A1

  公开（公告）日：2014-06-25

  Suggested is a cosmetic compositions comprising (a) a crosspolymer obtained from copolymerisation of at least two different polyols and at least one dicarboxylic acid and (b) at least one fragrance.

  建议的是一种化妆品组合物，包括 (a) 由至少两种不同的多元醇和至少一种二羧酸共聚得到的交联聚合物，以及 (b) 至少一种香料。

表征谱图