β-紫罗兰醇 | 22029-76-1

• 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: β-紫罗兰醇
• 中文别名: 4-(2,6,6-三甲基环己烯基-1-基)-3-丁烯-2-醇；4-(2,6,6-三甲基-1-环己烯-1-基)-3-丁烯-2-醇
• 英文名称: β-ionol
• 英文别名: β-Jonol；beta-Ionol；4-(2,6,6-Trimethylcyclohexen-1-yl)but-3-en-2-ol
• CAS: 22029-76-1
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: CNOPDZWOYFOHGN-UHFFFAOYSA-N

物化性质

• 沸点：
  107 °C3 mm Hg(lit.)
• 密度：
  0.928 g/mL at 20 °C(lit.)
• 闪点：
  93.4 °C
• LogP：
  4.33
• 稳定性/保质期：

  存在于烟叶中。

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.692
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 安全说明：
  S23,S24/25
• WGK Germany：
  2

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: β-Ionol
Product name
CAS-No. : 22029-76-1
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-ol
beta-Ionol
Formula : C13H22O
Molecular Weight : 194,31 g/mol

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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
Flush eyes with water as a precaution.
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
Indication of any immediate medical attention and special treatment needed
no data available

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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.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid breathing vapors, mist or gas. Remove all sources of ignition. Beware of vapours accumulating to
form explosive concentrations. Vapours can accumulate in low areas.
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.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid inhalation of vapour or mist.
Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic
charge.
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.
Store under inert gas. Air sensitive.
Specific end uses
no data available

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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
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.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
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).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: liquid
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 107 °C at 4 hPa
boiling range
g) Flash point 93 °C - closed cup
h) Evaporation 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 0,928 g/mL at 20 °C
n) Water solubility insoluble
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition 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

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks.
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
LD50 Dermal - rabbit - > 5.000 mg/kg
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
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
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: EM9630000

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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
no data available
Other adverse effects
no data available

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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.

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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

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

毒性

GRAS(FEMA)。

使用限量

FEMA(mg/kg)：

• 无醇饮料：1.0
• 冷冻乳品、乳制品、水果冰品、仿乳制品：1.5
• 凝胶品、布丁、糖食、糖霜、果酱、果冻：2.0
• 软糖：2.5
• 焙烤制品：3.0
• 硬糖：4.0
• 胶姆糖：5.0

化学性质

无色透明液体，沸点107℃(400Pa)，具有甜的花香和香酯暖香气，不溶于水但溶于油脂。天然存在于葡萄和草莓中。

用途

GB 2760～1996 规定其为允许使用的食品用香料，适用于配制玫瑰、薰衣草等香精。

生产方法

• 烟草提取：FC，第18号。
• 合成：通过β-紫罗兰酮还原获得。

反应信息

• 作为反应物：
  描述：

  β-紫罗兰醇 在 manganese(IV) oxide 、 正丁基锂 、 diazabicyclononane 、 水 、 silica gel 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 10.5h， 生成 视黄醛
  参考文献：
  名称：

  Pardoen, J. A.; Mulder, P. P. J.; Berg, E. M. M. van den, Canadian Journal of Chemistry, 1985, vol. 63, p. 1431 - 1435

  摘要：

  DOI：
• 作为产物：
  描述：

  beta-紫罗酮 在 C₂₉H₃₄BNOP₂Ru 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 以91%的产率得到β-紫罗兰醇
  参考文献：
  名称：

  以iPrOH或EtOH为氢源的α，β-不饱和羰基化合物的选择性无碱转移加氢

  摘要：

  商业上可买到的Ru‐MACHO TM ‐ BH是一种活性催化剂，可用于多个官能团的加氢和醇的脱氢。在此，我们报道了该催化剂在羰基化合物的无碱转移加氢中的新应用。即使使用α，β-不饱和羰基化合物作为底物，Ru‐MACHO TM ‐ BH在此转化过程中也被证明具有很高的活性和选择性。在很短的反应时间后，在温和的温度下，催化剂的负载量低至0.1-0.5 mol％，从而以优异的收率获得了相应的脂肪族，芳香族和烯丙基醇。这个协议可以容忍我PrOH和EtOH为氢源。此外，在不损失活性或选择性的情况下，可进行放大至几克的量。提出了一种外球机理，巴豆醛和1-苯基-丁-2-烯酮的计算动力学和热力学与实验完全吻合。

  DOI：

  10.1002/chem.201705423

文献信息

• HYDROGENATION OF ESTERS OR CARBONYL GROUPS WITH PHOSPHINO-OXIDE BASED RUTHENIUM COMPLEXES
  申请人：Saudan Lionel

  公开号：US20110190523A1

  公开（公告）日：2011-08-04

  The present invention relates to the field of catalytic hydrogenation and, more particularly, to the use of specific ruthenium catalysts or pre-catalysts in hydrogenation processes for the reduction of ketones, aldehydes, esters or lactones into their corresponding alcohols or diols respectively. The preferred catalysts are ruthenium complexes comprising a ligand of the type (N—N) type and a ligand of the type (P—PO).

  本发明涉及催化加氢领域，更具体地涉及在加氢过程中使用特定的钌催化剂或前驱体，用于将酮、醛、酯或内酯还原为相应的醇或二醇。首选催化剂是包含(N—N)型配体和(P—PO)型配体的钌配合物。
• Cyclopentadienyl–NHC Iron Complexes for Solvent‐Free Catalytic Hydrosilylation of Aldehydes and Ketones
  作者：David Bézier、Fan Jiang、Thierry Roisnel、Jean‐Baptiste Sortais、Christophe Darcel

  DOI：10.1002/ejic.201100762

  日期：2012.3

  Seven cyclopentadienyl-NHC piano-stool iron complexes were prepared and studied in the catalytic hydrosilylation of aldehydes and ketones under visible light irradiation. A significant acceleration of the rate was observed when the reactions were carried out under solvent-free conditions. Single-crystal X-ray structural analyses were performed for complexes 5 and 7.

  制备了七种环戊二烯基-NHC钢琴-凳铁配合物，并研究了可见光照射下醛和酮的催化氢化硅烷化反应。当反应在无溶剂条件下进行时，观察到速率显着加快。对配合物 5 和 7 进行了单晶 X 射线结构分析。
• Reduction of Carbonyl Compounds to their Corresponding of Alcohols with [Zn(BH4)2(2-MeOpy)] & [Zn(BH4)2(2-Mepy)] as New Reducing Agents (A Comparison Study)
  作者：BEHROOZ KHEZRI、FARNAZ NAJAF GHADIMI、CHONUR NEVISANDEH KARASHI、DAVOOD SETAMDIDEH

  DOI：10.13005/ojc/290233

  日期：2013.6.30

  The reduction of a variety of carbonyl compounds was efficiently carried out with (Zn(BH4)2(2-MeOpy)) and (Zn(BH4)2(2-Mepy)) as new reducing agents. The reduction reactions were performed to give the corresponding alcohols derivatives in perfect yields.

  使用（Zn（BH4）2（2-MeOpy））和（Zn（ ）2（2-Mepy））作为新的还原剂，可以有效地还原各种羰基化合物。进行还原反应以完美的产率得到相应的醇衍生物。
• Versatile Iridicycle Catalysts for Highly Efficient and Chemoselective Transfer Hydrogenation of Carbonyl Compounds in Water
  作者：Dinesh Talwar、Xiaofeng Wu、Ourida Saidi、Noemí Poyatos Salguero、Jianliang Xiao

  DOI：10.1002/chem.201403701

  日期：2014.9.26

  Cyclometalated iridium complexes are shown to be highly efficient and chemoselective catalysts for the transfer hydrogenation of a wide range of carbonyl groups with formic acid in water. Examples include α‐substituted ketones (α‐ether, α‐halo, α‐hydroxy, α‐amino, α‐nitrile or α‐ester), α‐keto esters, β‐keto esters and α,β‐unsaturated aldehydes. The reduction was carried out at substrate/catalyst ratios of

  环金属化铱配合物被证明是高效的化学选择催化剂，可用于在水中用甲酸转移多种羰基的加氢反应。实例包括α-取代的酮（α-醚，α-卤代，α-羟基，α-氨基，α-腈或α-酯），α-酮酸酯，β-酮酸酯和α，β-不饱和醛。在pH 4.5下，还原反应的底物/催化剂比例最高为50000，并且不需要有机溶剂。该方案为合成β-官能化的仲醇（例如β-羟基醚，β-羟胺和β-羟基卤化物）提供了一种实用，简便且有效的方法，它们是医药，精细化工，香料和农业化学合成中的重要中间体。
• Rabbit 3-hydroxyhexobarbital dehydrogenase is a NADPH-preferring reductase with broad substrate specificity for ketosteroids, prostaglandin D2, and other endogenous and xenobiotic carbonyl compounds
  作者：Satoshi Endo、Toshiyuki Matsunaga、Atsuko Matsumoto、Yuki Arai、Satoshi Ohno、Ossama El-Kabbani、Kazuo Tajima、Yasuo Bunai、Shigeru Yamano、Akira Hara、Yukio Kitade

  DOI：10.1016/j.bcp.2013.08.024

  日期：2013.11

  for NADP(H) over NAD(H) at a physiological pH of 7.4. In the NADPH-linked reduction, 3HBD showed broad substrate specificity for a variety of quinones, ketones and aldehydes, including 3-, 17- and 20-ketosteroids and prostaglandin D(2), which were converted to 3alpha-, 17beta- and 20alpha-hydroxysteroids and 9alpha,11beta-prostaglandin F(2), respectively. Especially, alpha-diketones (such as isatin

  3-羟基己异巴比妥脱氢酶（3HBD）催化将NAD（P）（+）链接的3-羟基己异巴比妥氧化为3-羟基己异巴比妥。该酶被认为是异生物醇和某些羟基类固醇的脱氢酶，但其生理功能仍然未知。我们已经纯化了兔3HBD，分离了其cDNA，并检查了其对辅酶和底物的特异性，反应方向性和组织分布。3HBD是醛酮还原酶（AKR）超家族的成员（AKR1C29），并且在7.4的生理pH值下，NADP（H）优于NAD（H）。在与NADPH相关的还原反应中，3HBD对多种醌，酮和醛（包括3-，17-和20-酮类固醇和前列腺素D（2））显示出广泛的底物特异性，它们被转化为3alpha-，17beta-和20alpha -羟基类固醇和9alpha，11beta-前列腺素F（2），分别。特别是，α-二酮（如isatin和diacetyl）和脂质过氧化衍生的醛（如4-oxo-和4-hydroxy-2-nonenals）是显示低K（m）值（0