2,6,6-三甲基-1-环己烯基乙醛 | 472-66-2

• 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 - 有机氧化合物
• 中文名称: 2,6,6-三甲基-1-环己烯基乙醛
• 中文别名: 2,6,6-三甲基-1-环己烯-1-乙醛；Β-环高柠檬醛；乙位环高柠檬醛；β-环高柠檬醛
• 英文名称: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde
• 英文别名: 2,6,6-trimethyl-1-cyclohexene-1-acetaldehyde；β-cyclohomocitral；2-(2,6,6-trimethylcyclohex-1-en-1-yl)acetaldehyde；β-homocyclocitral；2-(2,6,6-trimethylcyclohexen-1-yl)acetaldehyde
• CAS: 472-66-2
• 化学式: C₁₁H₁₈O
• mdl: MFCD00012057
• 分子量: 166.263
• InChiKey: VHTFHZGAMYUZEP-UHFFFAOYSA-N

物化性质

• 沸点：
  58-59 °C/0.4 mmHg (lit.)
• 密度：
  0.941 g/mL at 25 °C (lit.)
• 闪点：
  191 °F
• LogP：
  3.94
• 物理描述：
  A clear, colourless to pale yellow liquid; herbaceous aroma.
• 溶解度：
  Insoluble in water, soluble in fat
• 折光率：
  1.480-1.487
• 保留指数：
  1236;1237.3;1235
• 稳定性/保质期：
  1. 常温常压下稳定，为浅黄色液体，多溶于乙醇、丙二醇等试剂。
  2. 具有木香、青香、壤香、樟脑香以及玫瑰香气。
  3. 存在于主流烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.727
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2912299000
• 安全说明：
  S26,S36
• WGK Germany：
  3
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  常温、密闭、避光、存放在通风干燥处。

SDS

---

SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 472-66-2
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Skin irritation (Category 2), H315
Eye irritation (Category 2), H319
Specific target organ toxicity - single exposure (Category 3), H335
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xi Irritant R36/37/38
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing vapours.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
Other hazards - none

---

SECTION 3: Composition/information on ingredients
Substances
: β-Homocyclocitral
Synonyms
Formula : C11H18O
Molecular Weight : 166,26 g/mol
CAS-No. : 472-66-2
EC-No. : 207-454-0
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde
CAS-No. 472-66-2 Skin Irrit. 2; Eye Irrit. 2; STOT <= 100 %
EC-No. 207-454-0 SE 3; H315, H319, H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde
CAS-No. 472-66-2 Xi, R36/37/38 <= 100 %
EC-No. 207-454-0
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

---

SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with
water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

---

SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

---

SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid breathing vapours, mist or gas. Ensure adequate ventilation.
Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to
form explosive concentrations. Vapours can accumulate in low areas.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and
place in container for disposal according to local regulations (see section 13). Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

---

SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist.
Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic
charge.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Recommended storage temperature: 2 - 8 °C
Store under inert gas.
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

---

SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

---

SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: liquid
Colour: yellow
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and 58 - 59 °C at 0,5 hPa - lit.
boiling range
g) Flash point 88 °C - closed cup
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density 0,941 g/cm3 at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

---

SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks.
Incompatible materials
Strong oxidizing agentsStrong oxidizing agents, Strong bases, Strong acids
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

---

SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

---

SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

---

SECTION 13: Disposal considerations
Waste treatment methods
Product
This combustible material may be burned in a chemical incinerator equipped with an afterburner and
scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

---

SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

---

---

SECTION 15 - REGULATORY INFORMATION
N/A

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备方法：在乙醇钠的存在下，将柠檬醛与氯代醋酸乙酯进行缩合反应（Darzen Glycidic Ester Cordensation），随后加碱水解、脱羧，再加酸环化得到产物。

合成制备方法：同样在乙醇钠的存在下，先将柠檬醛与氯代醋酸乙酯进行缩合反应（Darzen Glycidic Ester Cordensation），然后依次进行加碱水解、脱羧和加酸环化，最终得到产物。

用途简介：该产品广泛应用于日化、烟草、食品等行业，是一种新型的广谱型合成香料。

用途：此产品适用于日化、烟草、食品等众多行业，属于一种新型的广谱型合成香料。

反应信息

• 作为反应物：
  描述：

  2,6,6-三甲基-1-环己烯基乙醛 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 γ-Homocyclogeranyl acetate
  参考文献：
  名称：

  Julia,M. et al., Bulletin de la Societe Chimique de France, 1960, p. 1732 - 1734

  摘要：

  DOI：
• 作为产物：
  描述：

  1-乙炔基-2,2,6-三甲基环己醇 在 vanadium tri-n-propoxide 、 苯甲酸 、 三苯基硅醇 作用下， 以 various solvent(s) 为溶剂， 以81%的产率得到2,6,6-三甲基-1-环己烯基乙醛
  参考文献：
  名称：

  （±）多边形的全部合成，由德·德·德雷门宁（de la drimenine）和德·德·德·德蒙尼（de la drimenine）合成，

  摘要：

  1，3，3-三甲基-2-乙烯基-1-环己烯的1,3,3-三甲基-2-乙烯基-1-环己烯的Diels-Alder加合物在动力学或热力学控制下通过碱进行异构化与二甲基乙炔二羧酸酯反应生成两种异构体，这些异构体在催化氢化后可提供高收率的原料用于合成反式和顺式drimanes。描述了由这些异构体之一的短的全合成（±）-多聚体和（±）-豆蔻碱。

  DOI：

  10.1016/s0040-4020(01)91850-2

文献信息

• [EN] PROTEIN TYROSINE PHOSPHATASE INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE PROTÉINE TYROSINE PHOSPHATASE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：CALICO LIFE SCIENCES LLC

  公开号：WO2020186199A1

  公开（公告）日：2020-09-17

  Provided herein are compounds, compositions, and methods useful for inhibiting protein tyrosine phosphatase, e.g., protein tyrosine phosphatase non-receptor type 2 (PTPN2) and/or protein tyrosine phosphatase non-receptor type 1 (PTPN1), and for treating related diseases, disorders and conditions favorably responsive to PTPN 1 or PTPN2 inhibitor treatment, e.g., a cancer or a metabolic disease.

  本文提供了用于抑制蛋白酪氨酸磷酸酶的化合物、组合物和方法，例如蛋白酪氨酸磷酸酶非受体型2（PTPN2）和/或蛋白酪氨酸磷酸酶非受体型1（PTPN1），以及用于治疗对PTPN1或PTPN2抑制剂治疗有良好反应的相关疾病、紊乱和状况的方法，例如癌症或代谢性疾病。
• Propylphosphonic Anhydride (T3P®): A Remarkably Efficient Reagent for the One-Pot Transformation of Aromatic, Heteroaromatic, and Aliphatic Aldehydes to Nitriles
  作者：John Augustine、Rajendra Atta、Balakrishna Ramappa、Chandrakantha Boodappa

  DOI：10.1055/s-0029-1218388

  日期：2009.12

  Propylphosphonic anhydride has been demonstrated to be an efficient reagent for the transformation of aromatic, heteroaromatic, and aliphatic aldehydes to respective nitriles in excellent yields. This procedure offers simple and one-pot access to nitriles and highlights the synthetic utility of T3P® as a versatile reagent in organic chemistry.

  三丙基膦酐已被证明是一种高效的试剂，可将芳香族、杂芳香族和脂肪族醛分别转化为相应的腈，产率极佳。这一过程提供了简单且一步制备腈的方法，并强调了T3P®作为一种多功能试剂在有机化学中的合成应用价值。
• Iron-Catalyzed Intramolecular Allylic C–H Amination
  作者：Shauna M. Paradine、M. Christina White

  DOI：10.1021/ja211600g

  日期：2012.2.1

  A highly selective C-H amination reaction under iron catalysis has been developed. This novel system, which employs an inexpensive, nontoxic [Fe(III)Pc] catalyst (typically used as an industrial ink additive), displays a strong preference for allylic C-H amination over aziridination and all other C-H bond types (i.e., allylic > benzylic > ethereal > 3° > 2° ≫ 1°). Moreover, in polyolefinic substrates

  已开发出铁催化下的高选择性 CH 胺化反应。这种新型系统采用廉价、无毒的 [Fe(III)Pc] 催化剂（通常用作工业油墨添加剂），显示出对烯丙基 CH 胺化的强烈偏好，而不是氮丙啶化和所有其他 CH 键类型（即，烯丙基 > 苄基> 空灵 > 3° > 2° ≫ 1°）。此外，在聚烯烃基材中，位点选择性可以通过烯丙基 CH 键的电子和空间特性来控制。尽管该反应显示为通过逐步机制进行，但 CH 胺化 3° 脂肪族 CH 键的立体保留性质表明，这是一个非常快速的自由基回弹步骤。
• Synthesen in der Carotinoid-Reihe. 3. Mitteilung. Die Synthese von 3,4; 3′,4′-Bisdehydro-β-carotin und 3,4-Monodehydro-β-carotin
  作者：O. Isler、H. Lindlar、M. Montavon、R. Rüegg、P. Zeller

  DOI：10.1002/hlca.19560390130

  日期：——

  3,4;3′,4′-Bisdehydro-β-carotene and 3,4-monodehydro-β-carotene are synthesized by building up the C40skeleton following the scheme C19 + C2 + C19 = C40. The synthesis of the symmetrical 3,4;3′,4′-bisdehydro-β-carotene is based on the use of two units of dehydro-β-C19-aldehyde. The asymmetrical 3,4-monodehydro-β-carotene is formed from one unit each of dehydro-β-C19-aldehyde and β-C19-aldehyde. 3,4;3′

  通过按照方案C 19 + C 2 + C 19＝ C 40构筑C 40骨架，合成了3,4; 3'，4'-双氢-β-胡萝卜素和3,4-单氢-β-胡萝卜素。的对称3,4-合成; 3'，4'-bisdehydro-β胡萝卜素是基于使用的脱氢-β-C的两个单元19 -醛。非对称3,4- monodehydro-β胡萝卜素从一个单元中的每个的脱氢-β-C形成19 -醛和β-C 19 -醛。3,4; 3'，4'-双去氢-β-胡萝卜素比3,4-单去氢-β-胡萝卜素形成更亮的红色溶液。在生长试验中，前者显示出38％的β-胡萝卜素活性，而后者显示了75％的β-胡萝卜素活性。
• [EN] OPSIN-BINDING LIGANDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] LIGANDS LIANT L'OPSINE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：BIKAM PHARMACEUTICALS INC

  公开号：WO2013081642A1

  公开（公告）日：2013-06-06

  Compounds and compositions are disclosed that are useful for treating ophthalmic conditions caused by or related to production of toxic visual cycle products that accumulate in the eye, such as dry adult macular degeneration, as well as conditions caused by or related to the misfolding of mutant opsin proteins and/or the mis-localization of opsin proteins. Compositions of these compounds alone or in combination with other therapeutic agents are also described, along with therapeutic methods of using such compounds and/or compositions. Methods of synthesizing such agents are also disclosed.

  揭示了用于治疗由于或与在眼睛中积聚的有毒视觉循环产物有关的眼科疾病的化合物和组合物，例如干性成人黄斑变性，以及由于或与突变视蛋白的错误折叠和/或视蛋白的错误定位有关的疾病。还描述了这些化合物单独或与其他治疗剂的组合物，以及使用这些化合物和/或组合物的治疗方法。还揭示了合成这些药剂的方法。

表征谱图