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桉叶油醇

桉叶油醇用途

Eucalyptol 是 5-HT3 受体, 钾通道, TNF-α 和 IL-1β 的抑制剂。

桉叶油醇名称

[ CAS 号 ]:
470-82-6

[ 中文名 ]:
桉叶油素

[ 英文名 ]:
Cineole

[中文别名 ]:

[英文别名 ]:

2-Oxa-1,3,3-trimethylbicyclo(2.2.2)octane
eucalyptol (cineole)
Terpan
2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-
2,2,4-trimethyl-3-oxabicyclo[2.2.2]octane
Eucapur
Zineol
Eukalyptol [Czech]
p-Menthane, 1,8-epoxy-
Eucalyptol

桉叶油醇生物活性

[ 描述 ]:

Eucalyptol 是 5-HT3 受体, 钾通道, TNF-α 和 IL-1β 的抑制剂。

[ 相关类别 ]:

信号通路 >> G 蛋白偶联受体/G 蛋白 >> 5-HT受体

信号通路 >> 神经信号通路 >> 5-HT受体

信号通路 >> 免疫及炎症 >> 白细胞介素相关

信号通路 >> 跨膜转运 >> 钾通道

信号通路 >> 细胞凋亡 >> TNF受体

研究领域 >> 神经疾病

天然产物 >> 萜类化合物和糖苷

[ 靶点 ]

5-HT3 Receptor

IL-1β

TNF-α

potassium channel

[体外研究]

桉油精抑制表达5-HT3受体的卵母细胞中5-HT诱发的电流,IC50为258μM[1]。桉叶素(Cin)处理以剂量依赖性方式显着降低Aβ25-35处理细胞中的ROS水平。桉叶油素处理以剂量依赖性方式显着降低Aβ25-35处理细胞中的NO水平(p <0.05和p <0.01)。与Aβ25-35处理的PC12细胞相比,桉油醇处理还以剂量依赖性方式显着降低Aβ25-35处理细胞中的IL-1β水平(p <0.05和p <0.01)。与Aβ25-35处理的细胞相比,桉油素以剂量依赖性方式减弱IL-6水平(p <0.05和p <0.01)[3]。

[体内研究]

结果显示,在处理的第7天至第50天,以最高剂量500和1000mg/kg用桉叶素(CIN)处理的雄性和雌性大鼠显示出比对照组更低的体重。在治疗的第一周,给予桉油精显着降低雄性大鼠(Eucalyptol 500和1000mg/kg)和雌性大鼠(Eucalyptol 1000mg/kg)的体重增加。然而,这种减少之后是用第二周的所有剂量治疗直至治疗结束的大鼠雄性和雌性的体重增加。对于雄性大鼠,平均红细胞体积(MCV)(桉叶素1000 mg/kg)显着增加6.93％,血小板计数(Eucalyptol 500和1000 mg/kg)分别显着增加43.54和38.98％并且减少平均红细胞血红蛋白浓度(MCHC)(Eucalyptol 500和1000 mg/kg)和平均血小板体积(MPV)分别为6.74和6.67％,分别为10.40,10.60和15.73％(Eucalyptol 100,500和1000 mg/kg),与对照组相比[4]。

[细胞实验]

桉树脑（Cineole）的保护剂量通过MTT染料摄取法测定。简而言之，将细胞（每孔1×104）接种在96孔组织培养板中，并使其在37℃的CO 2培养箱中粘附24小时。细胞在指定的时间段内分化。此后，在不同实验中用含有桉叶油素（0至10μM）的培养基替换培养基，持续最多24小时。将4μL/孔的四唑溴化物盐（5mg / mL PBS中的原液）加入100mL细胞悬浮液中，并将板温育4小时。在孵育期结束时，小心取出反应混合物，通过上下吸移数次向每个孔中加入200μLDMSO，直至内容物均匀化。将板在摇床上在室温下保持10分钟，然后使用酶标仪在550nm处读数[3]。

[动物实验]

瑞士小鼠用于该实验。将动物随机分成两组（n = 5）并禁食过夜，自由饮水。组对照接受1％吐温-80水溶液（0.1mL / 10g），另一组用桉油精单次2000mg / kg剂量口服给药。在口服治疗后30,60,120,180和240分钟观察动物，每天观察14天。每天记录行为变化，体重，食物和水消耗，临床毒性或死亡迹象[4]。

[参考文献]

[1]. Jarvis GE, et al. Noncompetitive Inhibition of 5-HT3 Receptors by Citral, Linalool, and Eucalyptol Revealed by Nonlinear Mixed-Effects Modeling. J Pharmacol Exp Ther. 2016 Mar;356(3):549-62.

[2]. Zeraatpisheh Z, et al. Eucalyptol induces hyperexcitability and epileptiform activity in snail neurons by inhibiting potassium channels. Eur J Pharmacol. 2015 Oct 5;764:70-8.

[3]. Khan A, et al. 1,8-cineole (eucalyptol) mitigates inflammation in amyloid Beta toxicated PC12 cells: relevance to Alzheimer's disease. Neurochem Res. 2014 Feb;39(2):344-52.[3]

[4]. Caldas GF, et al. Repeated-doses and reproductive toxicity studies of the monoterpene 1,8-cineole (eucalyptol) in Wistar rats. Food Chem Toxicol. 2016 Nov;97:297-306.

[相关活性小分子]

桉叶油醇物理化学性质

[ 密度 ]:
0.9±0.1 g/cm3

[ 沸点 ]:
174.0±8.0 °C at 760 mmHg

[ 熔点 ]:
1.5ºC

[ 分子式 ]:
C₁₀H₁₈O

[ 分子量 ]:
154.249

[ 闪点 ]:
50.9±15.3 °C

[ 精确质量 ]:
154.135757

[ PSA ]:
9.23000

[ LogP ]:
2.82

[ 外观性状 ]:
无色液体

[ 蒸汽压 ]:
1.6±0.3 mmHg at 25°C

[ 折射率 ]:
1.461

[ 储存条件 ]:
库房通风低温干燥,与氧化剂、酸,碱类分开存放

[ 稳定性 ]:
Stable. Flammable. Incompatible with acids, bases, strong oxidizing agents.

[ 水溶解性 ]:
水溶性：实际上不溶；水溶解度：3.5 g/l 21 °C；混溶：氯仿,醇,乙醚

桉叶油醇MSDS

详细MSDS(安全技术说明书)

桉叶油醇毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OS9275000

CHEMICAL NAME :: p-Menthane, 1,8-epoxy-

CAS REGISTRY NUMBER :: 470-82-6

LAST UPDATED :: 199710

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C10-H18-O

MOLECULAR WEIGHT :: 154.28

WISWESSER LINE NOTATION :: T66 A B AOTJ B1 B1 F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2480 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - coma

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1070 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - convulsions or effect on seizure threshold

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1500 mg/kg

TOXIC EFFECTS :: Skin and Appendages - dermatitis, other (after systemic exposure)

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 2250 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory stimulation

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 2 gm/kg

SEX/DURATION :: female 19-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - biochemical and metabolic

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 200 mg/L

REFERENCE :: EMMUEG Environmental and Molecular Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.10- 1987- Volume(issue)/page/year: 10(Suppl 10),1,1987 *** REVIEWS *** TOXICOLOGY REVIEW DPIRDU Dangerous Properties of Industrial Materials Report. (Van Nostrand Reinhold, 115 Fifth Ave., New York, NY 10003) V.1- 1981- Volume(issue)/page/year: 2(4),10,1982 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 19540 No. of Facilities: 1103 (estimated) No. of Industries: 11 No. of Occupations: 23 No. of Employees: 5213 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 19540 No. of Facilities: 4397 (estimated) No. of Industries: 48 No. of Occupations: 57 No. of Employees: 83399 (estimated) No. of Female Employees: 20158 (estimated)

桉叶油醇安全信息

[ 符号 ]:

GHS02

[ 信号词 ]:
Warning

[ 危害声明 ]:
H226

[ 警示性声明 ]:
P210-P370 + P378

[ 个人防护装备 ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ 危害码 (欧洲) ]:
Xi:Irritant

[ 风险声明 (欧洲) ]:
R10;R37/38;R41

[ 安全声明 (欧洲) ]:
S26-S39

[ 危险品运输编码 ]:
UN 1993

[ WGK德国 ]:
2

[ RTECS号 ]:
OS9275000

[ 包装等级 ]:
III

[ 危险类别 ]:
3.0

桉叶油醇合成路线

详细合成路线

桉叶油醇上下游产品

桉叶油醇上游产品

桉叶油醇下游产品

桉叶油醇制备

1、桉树脑广泛存在于天然芳香油中，为桉叶油的主要成分。桉树脑可以芳香油中单离制得。例如将桉叶油分馏，收集175-180℃馏分，稍加精制即可。如需制造纯度较高的产品，可将芳香油中分馏得到的桉树脑加以冷却，通入HCI干燥。分离出盐酸及桉树脑结晶，用热水分解结晶，再经精馏即得纯粹的桉树脑。合成法是将萜品转化成酸，再脱水而得。

2、由桉叶油、蓝桉油等含桉叶醇较多的精油，取170～180℃精馏分，经冷冻或在冷冻下分馏单离而得。

精制方法：将桉树脑与间苯二酚、邻苯二酚等生成的加成物用石油醚重结晶后，用水蒸气蒸馏法精制。也可将桉树脑用等体积的石油醚稀释，然后用溴化氢饱和，过滤出沉淀，用少量石油醚洗涤后放入水中搅拌，桉树脑即可再生。

3. 烟草：BU，9；OR，26；FC，18。

桉叶油醇文献

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J. Insect Physiol. 78 , 33-46, (2015)

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