小茴香醇 | 2217-02-9

• 物质功能分类: 香精与香料 - 合成香料 - 醇类香料
• 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: 小茴香醇
• 中文别名: (+)-葑醇；(1R)-1,3,3-三甲基双环[2.2.1]庚-2-醇；(1R)-endo-(+)-葑基醇；(+)-葑基醇
• 英文名称: (1R)-endo-(+)-fenchol
• 英文别名: (+)-fenchol；endo-fenchol；fenchyl alcohol；α-fenchol；(1R)-endo-(+)-fenchyl alcohol；(1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol；α-fenchyl alcohol；exo-fenchol
• CAS: 2217-02-9
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: IAIHUHQCLTYTSF-OYNCUSHFSA-N

物化性质

• 熔点：
  43-46 °C
• 沸点：
  201-202 °C(lit.)
• 密度：
  0.8389 (rough estimate)
• 闪点：
  165 °F
• 溶解度：
  氯仿（微溶）、乙醇（微溶）、甲醇（微溶）
• LogP：
  2.93 at 20℃ and pH6.37-6.5
• 物理描述：
  White to pale yellow crystals; Camphoraceous aroma
• 蒸汽压力：
  0.06 mmHg
• 稳定性/保质期：

  避免让氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• TSCA：
  Yes
• 安全说明：
  S22,S24/25
• 危险类别码：
  R36/38
• WGK Germany：
  2,3
• 海关编码：
  29061900
• 危险品运输编号：
  UN 1325 4.1/PG 2
• 储存条件：
  请将容器密封后存放在干燥、阴凉的地方，使用一个密封性好的储存器。

SDS

Name:	(1R)-endo-(+)-Fenchol 96% Material Safety Data Sheet
Synonym:	1,3,3-Trimethyl-2-norbornano
CAS:	2217-02-9

Section 1 - Chemical Product MSDS Name:(1R)-endo-(+)-Fenchol 96% Material Safety Data Sheet
Synonym:1,3,3-Trimethyl-2-norbornano

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2217-02-9	(1R)-endo-(+)-Fenchol	96	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.
Inhalation:
May cause respiratory tract irritation.
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 immediately.
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:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
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. Containers may explode when heated.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Use water spray to cool fire-exposed containers.

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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. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. 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. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat, sparks, and flame. 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 ventilation to keep airborne concentrations low.
Exposure Limits CAS# 2217-02-9: 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: Crystals
Color: Colorless Crystals
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 201 deg C @ 760.00mmHg
Freezing/Melting Point: 39.00 - 45.00 deg C
Autoignition Temperature: Not available.
Flash Point: 73 deg C ( 163.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H18O
Molecular Weight: 154.25

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong reducing agents, strong acids, acid chlorides, acid anhydrides.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2217-02-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1R)-endo-(+)-Fenchol - 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.
WGK (Water Danger/Protection)
CAS# 2217-02-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2217-02-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2217-02-9 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

毒性

毒性可安全用于食品（FDA，§172.515，2000）。

食品添加剂最大允许使用量及残留量标准

添加剂中文名称	允许使用该种添加剂的食品中文名称	添加剂功能	最大允许使用量（g/kg）	最大允许残留量（g/kg）
茴香醇	食品	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
小茴香醇	食品	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

化学性质

茴香醇有两种异构体：α-和β-。α-小茴香醇为无色至草黄色结晶，熔点40～45℃；β-小茴香醇在室温下为无色至淡黄色液体，沸点201～202℃，[α]D₂₀+10.5°±5°（乙醇中）。具有柑橘香调的樟脑样气味，并带有苦的白柠檬风味。微溶于水，易溶于乙醇。天然混合体存在于白云杉油和松树油等中。

用途

GB 2760—1996 规定为允许使用的食品用香料。

生产方法

由小茴香酮还原而得；也可由松萜烯制取。

反应信息

• 作为反应物：
  描述：

  小茴香醇 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 以95%的产率得到(1R)-1,3,3-三甲基二环[2.2.1]庚-2-酮
  参考文献：
  名称：

  醇和1,2-二醇的温和氧化剂：DMSO中的邻碘氧苯甲酸（IBX）

  摘要：

  邻碘氧苯甲酸（IBX）分别将伯醇和仲醇平滑氧化为醛和酮。1,2-二醇可转化为α-酮醇或α-二酮，而乙二醇CC键没有任何氧化裂解。IBX氧化很容易在室温下的DMSO溶液中进行，收率范围从良好到定量。

  DOI：

  10.1016/0040-4039(94)80038-3
• 作为产物：
  描述：

  (1R)-1,3,3-三甲基二环[2.2.1]庚-2-酮 在 氨 、 lithium 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.92h， 生成 小茴香醇
  参考文献：
  名称：

  碱金属-NH 3 -NH 4 +还原双环[2.2.1]庚-2-酮的内选择性和动力学控制

  摘要：

  还原5个双环[2.2.1]庚-2-酮（6），（9），（12），（15），（18）和母体双环[2.2.1]庚-5-烯-2-一种（21）通过将碱金属溶于NH 3和用NH 4 Cl饱和的助溶剂在每种情况下主要提供（83– <99％）相应的内醇（7），（10），（13），（16）），（19）和（22），并且由于这些内醇中的两种在热力学上更稳定[[ 7，（19）]和两个不太稳定的[（10），（13）]异构体，这些还原可能都是动力学控制的；酮（6），（9），（12），（15）和（21）中的这种内选择性和外氢交换之间存在相关性。

  DOI：

  10.1039/c39860001558
• 作为试剂：
  描述：

  (o-methoxyphenyl)methylphenylphosphine 在 四氯化碳 、 小茴香醇 作用下， 反应 24.0h， 以23%的产率得到
  参考文献：
  名称：

  [EN] CHIRAL PHOSPHORUS COMPOUNDS
  [FR] COMPOSES PHOSPHORES CHIRAUX

  摘要：

  一种立体选择性制备P-手性四配位磷化合物的方法，该方法包括将来自手性醇，手性胺或手性硫醇的第一反应物与包含P-手性三配位磷化合物的第二反应物在亲电试剂的存在下反应。

  公开号：

  WO2005118603A1

文献信息

• Diethylzinc-Mediated Radical 1,2-Addition of Alkenes and Alkynes
  作者：Xin Li、Songtao He、Qiuling Song

  DOI：10.1021/acs.orglett.1c00669

  日期：2021.4.16

  A novel diethylzinc-mediated radical 1,2-addition of perfluoroalkyl iodides to unactivated alkenes and alkynes is presented, which demonstrates a novel way to generate an ethyl difluoroacetate radical. This method is highly efficient and gives full conversions of the substrates, high yields of the products, and negligible byproducts and requires no column chromatography purifications. The mild conditions

  提出了一种新颖的由二乙基锌介导的全氟烷基碘与非活化烯烃和炔烃进行的1,2-基自由基加成反应，这表明了一种生成二氟乙酸乙酯基团的新方法。该方法非常高效，可实现底物的完全转化，产物的高收率和可忽略的副产物，并且不需要柱色谱法纯化。温和的条件使该协议能够表现出出色的官能团兼容性。
• 9-Azanoradamantane N-Oxyl (Nor-AZADO): A Highly Active Organocatalyst for Alcohol Oxidation
  作者：Masaki Hayashi、Yusuke Sasano、Shota Nagasawa、Masatoshi Shibuya、Yoshiharu Iwabuchi

  DOI：10.1248/cpb.59.1570

  日期：——

  A highly active organocatalyst for alcohol oxidation has been developed. 9-Azanoradamantane N-oxyl (Nor-AZADO 4), constituting an unhindered, stable nitroxyl radical, exhibits superior catalytic activity to 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and AZADOs in the oxidation of alcohols to their corresponding carbonyl compounds.

  已经开发出用于醇氧化的高活性有机催化剂。9-Azanoradamantane N-oxyl（Nor-AZADO 4）构成不受阻碍的稳定硝氧基自由基，在将醇氧化为2,2,6,6-四甲基哌啶-1-氧基（TEMPO）和AZADOs方面表现出优异的催化活性。它们相应的羰基化合物。
• Pyridine Alkaloid Derivatives of Dithiophosphoric Acids and Their Antimicrobial Evaluation
  作者：Ilyas S. Nizamov、Ildus D. Timushev、Ramazan Z. Salikhov、Ilnar D. Nizamov、Yevgeniy N. Nikitin、Marina P. Shulaeva、Oscar K. Pozdeev、Tatyana Yu. Voznesenskaya、Elvira S. Batyeva、Rafael A. Cherkasov

  DOI：10.14233/ajchem.2020.22381

  日期：2020.1.15

  series of (S)-(–)-nicotinium salts of cyclic dithiophosphoric acids were synthesized by the reactions of 5,5-dimethyl-2-mercapto-2-thiono-1,3,2-dioxaphosphorinane and 4-methyl-2-mercapto-2-thiono-1,3,2-dioxaphosphorinane with (S)-(–)-nicotine. Picolinic and nicotinic acids and potassium pyridine-3-carboxylate reacted with O,O-diterpenyl dithiophosphoric acids on the basis of (1R)-endo-(+)-fenchyl alcohol

  通过5,5-二甲基-2-巯基-2-硫代-1,3,2-二氧杂膦烷与4-甲基-二硫代磷酸反应合成了一系列新的环状二硫代磷酸(S)-(–)-烟鎓盐。 2-巯基-2-硫代-1,3,2-二氧杂膦烷与 (S)-(–)-尼古丁。吡啶甲酸和烟酸以及吡啶-3-羧酸钾与O,O-二萜基二硫代磷酸在(1R)-内-(+)-芬醇和(S)-(-)-薄荷醇的基础上反应，得到相应的2-羧基吡啶鎓、3-羧基吡啶鎓和吡啶鎓-3-羧酸二硫代磷酸钾。基于尼古丁和 O,O-二萜基二硫代磷酸盐的 (S)-(–)-nicotinium 4-methyl-2-mercapto-2-thiono-1,3,2-dioxaphosrinane 和盐的抗菌和抗真菌活性烟酰胺进行了评估。
• Photochemical Transformations with Iodine Azide after Release from an Ion‐Exchange Resin
  作者：Teresa Kösel、Göran Schulz、Gerald Dräger、Andreas Kirschning

  DOI：10.1002/anie.202003079

  日期：2020.7.20

  This report discloses the photochemical homolytic cleavage of iodine azide after its formation following release from polymer‐bound bisazido iodate(I) anions. A series of radical reactions are reported including the 1,2‐functionlization of alkenes and the unprecedented chemoselective oxidation of secondary alcohols in the presence of primary alcohols.

  该报告公开了叠氮化碘从聚合物结合的双碘叠氮碘酸盐（I）阴离子释放后形成后的光化学均裂。据报道发生了一系列自由基反应，包括烯烃的1,2-官能化以及在伯醇存在下仲醇前所未有的化学选择性氧化。
• A New Convenient Synthesis of Ethenyl Ethers
  作者：Elena Cabianca、Florence Chéry、Patrick Rollin、Sergio Cossu、Ottorino De Lucchi

  DOI：10.1055/s-2001-18757

  日期：——

  Addition-elimination of an alcohol to 1,2-bis(phenylsulfonyl)ethylene afforded β-alkoxyvinyl sulfones which were submitted to reductive elimination with 6% sodium amalgam to produce the corresponding ethenyl ethers in high yields and purity.

  醇对1,2-双(苯磺酰基)乙烯的加成-消除反应得到β-烷氧基乙烯基砜，再通过6%的钠汞齐进行还原消除，以高产率和高纯度生成相应的乙烯基醚。