(1S)-菊酸内酯 | 14087-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: (1S)-菊酸内酯
• 中文别名: (1S)-菊酸查尔酮
• 英文名称: 4,4,7,7-Tetramethyl-3-oxabicyclo<4.1.0>heptan-2-on
• 英文别名: 4,4,7,7-tetramethyl-3-oxabicyclo<4.1.0>heptan-2-one；(+/-)-Dihydrochrysanthemolactone；(+/-)-4,4,7,7-tetramethyl-3-oxa-norcaran-2-one；(+/-)-4,4,7,7-Tetramethyl-3-oxa-norcaran-2-on；(1S)-Chrysanthemolactone；(1S,6R)-4,4,7,7-tetramethyl-3-oxabicyclo[4.1.0]heptan-2-one
• CAS: 14087-71-9
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: XAKBEOUVVTWXNF-RNFRBKRXSA-N

物化性质

• 熔点：
  80-83 °C
• 沸点：
  257.18°C (rough estimate)
• 密度：
  0.9812 (rough estimate)
• LogP：
  1.720 (est)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2932209090

SDS

Name:	(1S)-Chrysanthemolactone 99+% Material Safety Data Sheet
Synonym:	(1S,3R)-4,4,7,7-Trimethyl-3-Oxabicyclo[4.1.0]Heptan-2-One
CAS:	14087-71-9

Section 1 - Chemical Product MSDS Name:(1S)-Chrysanthemolactone 99+% Material Safety Data Sheet
Synonym:(1S,3R)-4,4,7,7-Trimethyl-3-Oxabicyclo[4.1.0]Heptan-2-One

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
14087-71-9	(1S)-Chrysanthemolactone	99+%	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. 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.
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.
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:

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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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Use agent most appropriate to extinguish fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

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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# 14087-71-9: 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 and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: yellow-beige
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 80.00 - 83.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: practically insoluble
Specific Gravity/Density:
Molecular Formula: C10H16O2
Molecular Weight: 168.24

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 14087-71-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1S)-Chrysanthemolactone - 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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 14087-71-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 14087-71-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 14087-71-9 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

反应信息

• 作为反应物：
  描述：

  (1S)-菊酸内酯 生成 4,5-二氢-5,5-二甲基-4-(2-甲基-1-丙烯基)呋喃-2(3H)-酮
  参考文献：
  名称：

  菊花羧酸。III.-菊酸的内酯化

  摘要：

  (±)-cis-Chrysanthemic acid 在沸腾的稀硫酸中很容易内酯化为结晶的 (±)-cis-dihydrochrysanthemo-δD-内酯。内酯环通过碱水解开环，得到(±)-顺-δD-羟基二氢菊酸的衍生物。用甲醇硫酸打开内酯环主要得到(±)-顺-±-甲氧基二氢菊酸甲酯和(±)-顺-菊酸甲酯。相反，(±)-反-菊酸在类似条件下转化为结晶的(±)-反-δ-羟基二氢菊酸。讨论了这些反应的机制及其对除虫菊测定的 Seil 和 Wilcoxon-Holaday 方法的影响。在 300°C 下加热。在密封管中，(±)-cis-和 (±)-trans-菊酸和 (±)-cis-dihydrochrysanthemo-δ-内酯被转化为异构结晶内酯，(±)-pyrocin。这表明氧化降解不是二氢菊花-内酯，而是 (±)-β-异丁烯基异己基-σ-内酯。这些内酯对家蝇基本上无毒。

  DOI：

  10.1002/jsfa.2740020909
• 作为产物：
  描述：

  methyl 2-acetyl-3-methylbut-2-enoate 在 palladium on activated charcoal manganese(IV) oxide 、 aluminum oxide 、 正丁基锂 、 氢气 、 sodium hydride 、 potassium n-butoxide 、 一水合肼 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 、 苯 为溶剂， 反应 16.5h， 生成 (1S)-菊酸内酯
  参考文献：
  名称：

  立体定向环丙烯酸合成顺-菊基甲基酯2。绕过重氮烷的方法（1）。

  摘要：

  描述了通过环丙烯的催化氢化的立体定向合成顺式菊酸酯。所需的前体，3H吡唑，通过新颖的二价阴离子反应和MnO这里获得2一个Δ的脱氢2 -吡唑啉，而不是更笨重diazoaddition方法。

  DOI：

  10.1016/s0040-4039(00)87119-1

文献信息

• (+)-Trans-chrysanthemic acid from (+)-Δ3-carene
  作者：R. Sobti、Sukh Dev

  DOI：10.1016/s0040-4020(01)97467-8

  日期：1974.1

  A new and more efficient route for the conversion of the readily available (+)-Δ3-carene into (+)-trans-chrysanthemic acid is described.

  为容易获得的转化新的和更有效的路由（+） - Δ 3 -carene成（+） -反式-chrysanthemic酸进行说明。
• Electrooxidative cleavage of carbon-carbon bonds. 2. Double cleavage of .alpha.,.beta.-epoxy alkanones and enantiospecific syntheses of chiral methyl trans- and cis-chrysanthemates from (+)- and (-)-carvones
  作者：Sigeru Torii、Tsutomu Inokuchi、Ryu Oi

  DOI：10.1021/jo00160a002

  日期：1983.6
• The chrysanthemumcarboxylic acids. V.—hydration of the chrysanthemic acids
  作者：S. H. Harper、R. A. Thompson

  DOI：10.1002/jsfa.2740030508

  日期：1952.5

  AbstractIn boiling dilute sulphuric acid hydration of (±)‐trans‐chrysanthemic acid occurs to give the crystalline (±)‐trans‐δ‐hydroxydihydrochrysanthemic acid. In like manner (+)‐and (‐)‐trans‐chrysanthemic acids yield the crystalline (‐)‐ and (+)‐trans‐δ‐hydroxy‐dihydrochrysanthemic acids respectively. No racemization occurs as the recovered ( + )‐and ( ‐ )‐trans‐chrysanthemic acids have unchanged specific rotation.The lactonization of (±)‐cis‐chrysanthemic acid to (±)‐cis‐dihydrochrysanthemo‐δ‐lactone in boiling dilute sulphuric acid is shown to be reversible and to constitute an example of lacto‐enoic tautomerism. ( + )‐ and ( ‐ )‐cis‐Chrysanthemic acids are similarly lactonized to the crystalline (+)‐ and (‐)‐cis‐dihydrochrysanthemo‐δ‐lactones. The latter lactone is not identical with (‐)‐pyrocin, whose structure is confirmed as (‐)‐β‐isobutenyliso‐hexano‐γ‐lactone.
• Crammer, Bernard; Goldschmidt, Zeev; Ikan, Raphael, Journal of the Chemical Society. Perkin transactions I, 1984, # 5, p. 887 - 891
  作者：Crammer, Bernard、Goldschmidt, Zeev、Ikan, Raphael、Cohen, Shmuel

  DOI：——

  日期：——
• Lochynski, S.; Jarosz, B.; Walkowicz, M., Journal fur praktische Chemie (Leipzig 1954), 1988, vol. 330, # 2, p. 284 - 288
  作者：Lochynski, S.、Jarosz, B.、Walkowicz, M.、Piatkowski, K.

  DOI：——

  日期：——