homoterpenylmethylketone | 4436-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: homoterpenylmethylketone
• 英文别名: 5,5-dimethyl-4-(3-oxobutyl)-2(3H)-dihydrofuranone；5,5-dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone；Homoterpenyl methyl ketone；5,5-dimethyl-4-(3-oxo-butyl)-dihydro-furan-2-one；(+/-)-3-(α-hydroxy-isopropyl)-6-oxo-heptanoic acid-lactone；(+/-)-3-(α-Hydroxy-isopropyl)-6-oxo-heptansaeure-lacton；2(3H)-Furanone, dihydro-5,5-dimethyl-4-(3-oxobutyl)-；5,5-dimethyl-4-(3-oxobutyl)oxolan-2-one
• CAS: 4436-81-1
• 化学式: C₁₀H₁₆O₃
• mdl: MFCD00022486
• 分子量: 184.235
• InChiKey: AWQSAIIDOMEEOD-UHFFFAOYSA-N

物化性质

• 沸点：
  278.19°C (rough estimate)
• 密度：
  1.0683 (rough estimate)
• 保留指数：
  1558.3

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932209090

SDS

---

Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 4-HYDROXY-4-METHYL-3-(3-OXOBUTYL)-
VALERIC ACID GAMMA-LACTONE
CAS-No. : 4436-81-1
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 [EU-GHS/CLP]
Acute toxicity, Oral (Category 4)
Eye irritation (Category 2)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. Irritating to eyes.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H319 Causes serious eye irritation.
Precautionary statement(s)
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
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
R36 Irritating to eyes.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
Other hazards - none

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C10H16O3
Molecular Weight : 184,24 g/mol
Component Concentration
4-HYDROXY-4-METHYL-3-(3-OXOBUTYL)-VALERIC ACID GAMMA-LACTONE
CAS-No. 4436-81-1 -

---

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
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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Indication of immediate medical attention and special treatment needed
no data available

---

Section 5. FIRE-FIGHTING 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
Precautions for fire-fighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

---

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. 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 formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

---

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
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use
respirators and components tested and approved under appropriate government standards such as
NIOSH (US) or CEN (EU).

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting/freezing point no data available
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
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 no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 0,341
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

---

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

---

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 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 Harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Additional Information
RTECS: Not available

---

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

---

Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional
waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent
and burn in a chemical incinerator equipped with an afterburner and scrubber.
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 users
no data available

---

---

SECTION 15 - REGULATORY INFORMATION
N/A

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  homoterpenylmethylketone 在 potassium permanganate 作用下， 生成 citric acid
  参考文献：
  名称：

  Hueckel; Nerdel, Justus Liebigs Annalen der Chemie, 1937, vol. 528, p. 57,64

  摘要：

  DOI：
• 作为产物：
  描述：

  α-Terpineolnitrosochlorid 在 甲醇 、 乙醚 、 mineral acid 、 羟胺 、 亚硝酸 作用下， 生成 homoterpenylmethylketone
  参考文献：
  名称：

  Cusmano; Linari, Gazzetta Chimica Italiana, 1912, vol. 42 I, p. 6

  摘要：

  DOI：

文献信息

• Development of isoindoline nitroxides for EPR oximetry in viable systems
  作者：J. Shen、S. Bottle、N. Khan、O. Grinberg、D. Reid、A. Micallef、H. Swartz

  DOI：10.1007/bf03166117

  日期：2002.9

  Nitroxides are widely used as biophysical probes to study molecular motion, intracellular oxygen, pH, transmembrane potential, and cellular redox metabolism, etc. They may be rapidly metabolized to hydroxylamines by cells, which limits their use in viable systems. In this study, we have characterized relevant properties in cells of several isoindoline nitroxides that have been prepared to have different

  氮氧化物被广泛用作生物物理探针来研究分子运动、细胞内氧、pH、跨膜电位和细胞氧化还原代谢等。它们可能会被细胞迅速代谢为羟胺，这限制了它们在可行系统中的应用。在这项研究中，我们表征了几种异吲哚啉氮氧化物在细胞中的相关特性，这些化合物已制备成具有不同的物理化学特性：1,1,3,3-四甲基异吲哚啉-2-yloxyl (TMIO) 及其类似物 5-carboxy-1， 1,3,3-四甲基异吲哚啉-2-yloxyl (CTMIO), 5-(N,N,N-trimethylammonio)-1,1,3,3-四甲基异吲哚啉-2-yloxyl iodide (QATMIO) 和 2-羟基- 1,1,3,3-四甲基异二氢吲哚盐酸盐 (TMIOH.HCl)。在 CHO 细胞中用 1-oxyl-2、2、6、6-四甲基-4-哌啶酮（Tempone）和3-羧基-2,2,5,5-四甲基-吡咯烷-1-氧基（PCA）。通过
• Terpenoids Biotransformation in Mammals III: Biotransformation of α-Pinene, β-Pinene, Pinane, 3-Carene, Carane, Myrcene, and p-Cymene in Rabbits
  作者：T. Ishidax、Y. Asakawa、T. Takemoto、T. Aratani

  DOI：10.1002/jps.2600700417

  日期：1981.4

  The biotransformation of (+)-, (-)-, and (+-)-alpha-pinenes, (-)-beta-pinene (nopinene), (-)-cis-pinane, (+)-3-carene, (-)-cis-carane, myrcene, and p-cymene in rabbits was investigated. The major metabolites were as follows: (-)-trans-verbenol from (+)-, (-)-, and (+/-)-alpha-pinenes; (-)-10-pinanol and (-)-1-p-menthene-7,8-diol from (-)-beta-pinene; (-)-alpha-terpineol and (-)-trans-sobrerol from

  （+）-，（-）-和（+-）-α-pine烯，（-）-β-pine烯（nopinene），（-）-顺-pin烷，（+）-3-carene，研究了兔体内的（-）-顺式香菜烷，月桂烯和对伞花烃。主要代谢物如下：（+）-，（-）-和（+/-）-α-pine烯的（-）-反式马鞭草酚；（-）-β-pine烯的（-）-10-pin醇和（-）-1-对-薄荷烯-7,8-二醇; （-）-顺式pin烷的（-）-α-松油醇和（-）-反式-细柏油；（-）-m-mentha-4,6-dien-8-ol，3-caren-9-ol，（-）-3-carene-9-羧酸和3-carene-9,10-二羧酸来自（+）-3-carene; （-）-顺式-戊烷中的9,10-二羧酸环烷; 和来自对-异丙基的月桂烯-3（10）-二醇，月桂烯-1,2-二醇，尿萜萜和对-异丙基-9-羧酸。这些新陈代谢包括烯丙基氧化，环氧化，立体选择性的
• Non-heme iron catalysis in C C, C–H, and CH2 oxidation reactions. Oxidative transformations on terpenoids catalyzed by Fe(bpmen)(OTf)2
  作者：David Clemente-Tejeda、Alejandro López-Moreno、Francisco A. Bermejo

  DOI：10.1016/j.tet.2013.02.013

  日期：2013.4

  The oxidation of terpene olefins with hydrogen peroxide in the presence of the non-hemo catalyst 5a afforded mixtures of epoxides whose composition was dependent upon the oxidation protocol used in each case. With terpenoid enones, the mixtures obtained evolved from clean epoxidation of α-ionone 23 to the clean allylic oxidation of damascone 28 due to the progressive deactivation of the electron density

  在非血液催化剂5a的存在下用过氧化氢氧化萜烯，得到环氧化物的混合物，其组成取决于每种情况下使用的氧化方案。对于萜类烯酮，由于在该系列中存在的双键上的电子密度的逐渐失活，获得的混合物从α-紫罗兰酮23的纯环氧化演变成大马士革28的纯烯丙基氧化。 双环和三环萜类化合物的氧化提供了从环氧化到烯烃降解，亚甲基和亚甲基活化产物的氧化产物。可能最吸引人的结果是由三环醚45合成马格努斯内酯46，收率为88％，转化率为100％。
• Etudes sur les mati�res v�g�tales volatiles XVII. Sur la synth�se dud,l-?4-car�ne � partir de la pip�rit�none
  作者：Y. R. Naves、G. Papazian

  DOI：10.1002/hlca.19420250520

  日期：1942.8.1

  L'identité de l'hydrocarbure obtenu par réduction Wolff-Kishner de l'hydrazone de la pipériténone comme d,l-Δ4-carène est confirmée par la caractérisation des produits de son oxydation: l'acide d,l-cis-1,1-diméthyl-2[γ-oxobutyl]-cyclopropane-carboxylique-(3) et les acides d,l-caroniques.

  L'identitéDE L'hydrocarbure obtenu PAR减小沃尔夫- Kishner DE L'腙德拉pipériténoneCOMME d，L -Δ 4 -carèneESTconfirmée面值拉caractérisationDES PRODUITS德子oxydation：L'acide d，L -顺式，1-二癸基-2 [γ-氧丁基]-环丙烷-羧基-（3）等酸d，1- caroniques。
• The Synthesis of Carvone from α-Terpinyl Acetate
  作者：Takayuki Suga

  DOI：10.1246/bcsj.31.569

  日期：1958.5

  (1) Oxidation of dl-α-terpineol with tert-butyl chromate yeilded 8-hydroxypiperitone, which has not previously been described, 8-hydroxycarvotanacetone and homoterpenyl methyl ketone. In this case the oxidative fission of the double bond in the ring took place to a remarkable extent.(2) Oxidation of dl-α-terpinyl acetate with tert-butyl chromate gave 8-acetoxypiperitone, 8-acetoxycarvotanacetone, (neither have previously been described) and homoterpenyl methyl ketone. In this oxidation the cleavage of the ethylenic linkage was suppressed, and the yield of 8-acetoxycarvotanacetone was relatively good.Moreover, the effects of the solvent, acetic acid, benzoyl peroxide, air and the reaction temperature, on the yield of 8-acetoxycarvotanacetone wre investigated.(3) 8-acetoxycarvotanacetone was converted into dl-carvone when acetic acid was eliminated by pyrolysis.(4) The synthesis of carvone from α-terpinyl acetate was attiained through the intermeidate of 8-acetoxycarvotanacetone The overall of carvone from α-terpinyl acetate was 28% mole%.

  (1) 用铬酸叔丁酯氧化 dl-α-松油醇，产生了以前从未描述过的 8-羟基哌啶酮、8-羟基香芹烷丙酮和均三萜甲基酮。(2)用铬酸叔丁酯氧化醋酸 dl-α-叔品酯，可得到 8-乙酰氧基哌啶酮、8-乙酰氧基香芹酮（以前均未描述过）和均质甲基酮。此外，还研究了溶剂、醋酸、过氧化苯甲酰、空气和反应温度对 8-acetoxycarvotanacetone 收率的影响。(4) 通过 8-acetoxycarvotanacetone 的中间产物获得了由α-松油基乙酸酯合成卡酮的方法。

表征谱图