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(+)-薄荷酮 | 3391-87-5

中文名称
(+)-薄荷酮
中文别名
(1S,4R)-对-薄荷烷-3-酮;(2R,5S)-2-异丙基-5-甲基环己酮
英文名称
l-menthone
英文别名
menthone;D-menthone;(2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-one
(+)-薄荷酮化学式
CAS
3391-87-5
化学式
C10H18O
mdl
——
分子量
154.252
InChiKey
NFLGAXVYCFJBMK-DTWKUNHWSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    209-210 °C(lit.)
  • 密度:
    0.893 g/mL at 20 °C(lit.)
  • 闪点:
    72 °C
  • 溶解度:
    氯仿(微溶)、乙醇(微溶)、甲醇(微溶)
  • LogP:
    2.625 (est)
  • 物理描述:
    colourless to pale yellowish liquid with a mint-like odour
  • 颜色/状态:
    Colorless, oily, mobile liq
  • 气味:
    Slight peppermint odor
  • 味道:
    Bitter
  • 分解:
    When heated to decomposition it emits acrid smoke and irritating fumes.
  • 折光率:
    INDEX OF REFRACTION: 1.4480-1.4520 @ 20 °C; SPECIFIC OPTICAL ROTATION: + OR - 2 DEG /DL-FORM/

计算性质

  • 辛醇/水分配系数(LogP):
    2.7
  • 重原子数:
    11
  • 可旋转键数:
    1
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.9
  • 拓扑面积:
    17.1
  • 氢给体数:
    0
  • 氢受体数:
    1

ADMET

代谢
酮类(例如香芹酮薄荷酮)被还原成二级醇,然后这些二级醇作为葡萄糖苷酸被排出体外。薄荷酮通过不对称还原转化为新薄荷醇,再通过葡萄糖苷酸结合转化为薄荷基葡萄糖苷酸。
...KETONES (EG CARVONE & MENTHONE) ARE REDUCED TO SECONDARY ALCOHOLS WHICH ARE THEN EXCRETED AS GLUCURONIDES. MENTHONE, ASYMMETRIC REDUCTION /TO/ NEO-MENTHOL, GLUCURONIDE CONJUGATION /TO/ MENTHYL GLUCURONIDE.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 副作用
神经毒素 - 其他中枢神经系统神经毒素
Neurotoxin - Other CNS neurotoxin
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
毒理性
  • 非人类毒性摘录
向大鼠胃内给予3毫摩尔/公斤的孟烯酮,可以抑制肝脏S-3-羟基-3-甲基戊二酸辅酶A还原酶的活性50%。
ADMIN OF 3 MMOL/KG MENTHONE, INTRAGASTRICALLY TO RATS INHIBITED HEPATIC S-3-HYDROXY-3-METHYLGLUTARYL-COA REDUCTASE BY 50%.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 非人类毒性摘录
四种植物(两种薰衣草、薄荷和桉树)的精油及其主要成分,即芳樟醇乙酸芳樟酯茴香酮薄荷酮、薄荷醇和桉树脑,在体外测试了对仓储食品中的害螨——长角扁谷盗的杀螨活性。进行了两种不同的程序来测试这些化合物的活性,一种是通过直接接触,另一种是通过吸入。在直接接触测试中,将每种未稀释物质的五种不同数量(6、2、1、0.5和0.25微升)涂抹在6厘米培养皿的内部表面,每个培养皿含有10只螨虫。通过吸入的活性测试使用了两种不同大小的培养皿:较小的6厘米培养皿,含有10只螨虫,上面覆盖有滤纸盘,并封闭在一个较大的9厘米培养皿中,其中含有6盎司2毫升的每种未稀释物质。在最高剂量下,两种薰衣草和薄荷的精油通过直接接触和吸入的方式杀死了100%的螨虫。桉树油活性最低。在精油成分中,薄荷醇显示出最高的活性,在直接接触时最低剂量(0.25微升)和吸入时6微升就能杀死100%的螨虫。然而,芳樟醇茴香酮薄荷酮也显示出良好的杀螨活性。与它所属的精油一样,桉树脑的活性最低。
Essential oils of four plants (two species of lavender, peppermint, and a eucalyptus) and some of their principal constituents, i.e., linalool, linalyl acetate, fenchone, menthone, menthol, and eucalyptol, were tested in vitro for their acaricidal activity against Tyrophagus longior, a mite species that is a pest in stored food. Two different procedures were carried out to test the activity of these compounds by direct contact and by inhalation. In the direct contact assays five different quantities of each undiluted substance (6, 2, 1, 0.5, and 0.25 ul) were spread on the internal surface of 6-cm petri dishes, each containing 10 mites. The activity by inhalation was tested using two petri dishes of different sizes: the smaller one (6 cm), containing 10 mites, was covered with a filter paper disk and enclosed in a bigger dish (9 cm) containing 6 oz 2 mul of each undiluted substance. At the highest doses, the essential oils of the two lavender species and of peppermint killed 100% of the mites, both by direct contact and by inhalation. Eucalyptus oil was the least active. Among the essential oil constituents, menthol showed the highest activity, killing 100% of the mites at the lowest dose (0.25 ul) by direct contact and at 6 ul by inhalation. However, linalool, fenchone, and menthone also showed good acaricidal activity. Eucalyptol, like the essential oil of which it is the principal constituent, had the lowest activity.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 非人类毒性摘录
Menthone是薄荷油的一个组成部分,它被口服给予10只雄性和10只雌性大鼠,剂量平分别为0、200、400和800 mg/kg体重/天,持续28天。在第19天之后,最高剂量组的雌性大鼠的剂量降低到了400 mg/kg体重。对血浆的分析显示,肌酐含量随着剂量的增加而剂量依赖性地减少,碱性磷酸酶活性和胆红素随着剂量的增加而剂量依赖性地增加。肝脏和脾脏的相对重量增加了。在两个最高剂量组的动物的小脑白质中,组织病理学上观察到了类似囊肿的空间。在这项研究中,Menthone的无效应平低于200 mg/kg体重/天。
Menthone, a component of peppermint oil, was given p.o. to groups of 10 male and 10 female rats at dose levels of 0, 200, 400 and 800 mg/kg bw/day, respectively, for 28 days. After 19 days the dose was reduced to 400 mg/kg bw in the female group receiving the highest dose. Analyses of plasma showed a dose-dependent decrease in creatinine content and a dose-dependent increase in alkaline phosphatase activity and bilirubin. The relative weights of liver and spleen were increased. Cyst-like spaces were seen histopathologically in the white matter of the cerebellum of the two highest dose groups. The no-effect level for menthone in this study was lower than 200 mg/kg bw/day.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 非人类毒性摘录
Menthone 对兔子的皮肤有轻微的刺激性,且在兔子身上急性皮肤毒性较低。在一项使用稀释溶液的志愿者研究中,没有发现致敏潜力的证据。在大鼠身上,Menthone 显示出中等到低度的急性口服毒性。在重复口服给药后,Menthone 导致大鼠肝脏、肾脏和脾脏的重量增加。在细菌沙门氏菌(Ames试验)中报告了致突变活性。
Menthone was a mild skin irritant and of low acute dermal toxicity in rabbits. No evidence of sensitizing potential was found in a volunteer study with a dilute solution. In rats, menthone demonstrated a moderate to low acute oral toxicity. On repeated oral administration, menthone produced increases in liver, kidney and spleen weights of rats. Mutagenic activity was reported in the bacterium Salmonella typhimurium (Ames test).
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 安全说明:
    S23,S24/25
  • WGK Germany:
    3
  • 海关编码:
    2914299000
  • 储存条件:
    2-8°C

SDS

SDS:a082f4474c6254d4f0af558afdeb79ab
查看

SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : (+)-Menthone
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. : 3391-87-5
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
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

SECTION 3: Composition/information on ingredients
Substances
Synonyms : (1S,4R)-p-Menthan-3-one
(2R,5S)-2-Isopropyl-5-methylcyclohexanone
Formula : C10H18O
Molecular Weight : 154,25 g/mol
CAS-No. : 3391-87-5
EC-No. : 222-227-6
No components need to be disclosed according to the applicable regulations.

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
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
For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large
fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or
spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of
water.
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
Avoid breathing vapours, mist or gas. Remove all sources of ignition. 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 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)
A part 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
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).
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: clear, liquid
Colour: colourless
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 209 - 210 °C - lit.
boiling range
g) Flash point 72 °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 0,893 g/cm3 at 20 °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 agents
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
no data available
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.

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. Contact a licensed
professional waste disposal service to dispose of this material.
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

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    (+)-薄荷酮葡萄糖 、 (-)-menthone:(+)-neomenthol reductase 、 glucose dehydrogenase from Pseudomonas sp 、 nicotinamide adenine dinucleotide phosphate 作用下, 以 乙醇 为溶剂, 反应 10.0h, 以63%的产率得到(1Alpha,2Alpha,5β)-(+-)-5-甲基
    参考文献:
    名称:
    确定短链脱氢酶/还原酶中酮还原和“烯”还原之间的机制转换。
    摘要:
    薄荷精油生物合成途径的三种酶具有高度同源性,即酮还原酶(-)-薄荷酮:(-)-薄荷醇还原酶和(-)-薄荷酮:(+)-新薄荷醇还原酶,以及“烯”还原酶异哌酮还原酶. 我们在最后两个中发现了一种罕见的催化残基取代,并进行了比较晶体结构分析和残基交换诱变,以研究这是否决定了反应结果。结果是天然活性的完全丧失以及烯还原和酮还原之间的转换。这表明催化谷氨酸与酪氨酸残基在确定 α,β-不饱和烯烃还原结果中的重要性,因为底物占据不同的结合构象,也可能与两个残基的相对酸度有关。
    DOI:
    10.1002/anie.201603785
  • 作为产物:
    描述:
    (+)-香茅醛 在 1.206wt% of ruthenium and 1.516wt% of copper supported metal organic framework 作用下, 10.0 ℃ 、300.01 kPa 条件下, 反应 15.0h, 以99.87%的产率得到
    参考文献:
    名称:
    一种由R-香茅醛制备L-薄荷酮的方法
    摘要:
    本发明公开了一种由R‑香茅醛制备L‑薄荷酮的方法,在Ru‑Cu‑MOF催化剂存在下将R‑香茅醛环化制备L‑薄荷酮,所述反应条件温和,反应对映选择性为90%~99.5%,转化率可达到95‑99.9%,薄荷酮ee值可达到90~99.9%。
    公开号:
    CN110903173B
  • 作为试剂: