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(-)-薄荷醇

(-)-薄荷醇用途

(-)-Menthol 是薄荷油的关键成分,(-)-Menthol 结合并激活瞬瞬时受体电位 M8 (TRPM8),TRPM8 是 Ca2+-可渗透的非选择性阳离子通道,最终增加 [Ca2+]i[1]。具有抗肿瘤活性[1]。

(-)-薄荷醇名称

[ CAS 号 ]:
2216-51-5

[ 中文名 ]:
L-薄荷醇

[ 英文名 ]:
L-Menthol

[中文别名 ]:

[英文别名 ]:

(-)-(1R,3R,4S)-Menthol
(−)-menthol
(-)-trans-p-Methan-cis-3-ol
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol
L-Menthol
(-)-(1R,2S,5R)-Menthol
(1R)-(-)-Menthol
DL-Menthol
(-)-p-Menthan-3-ol
MFCD00062979

(-)-薄荷醇生物活性

[ 描述 ]:

[ 相关类别 ]:

信号通路 >> 跨膜转运 >> TRP频道

研究领域 >> 癌症

[ 靶点 ]

TRPM8[1]

[体外研究]

(-)-薄荷醇(薄荷醇)本身不具有抗增殖活性,但能够增强LNCaP细胞中1α,25(OH)2D3介导的生长抑制。在高(-)-浓度超过1.6 mM的薄荷醇时,细胞开始从培养皿中分离[1]。 (-)-薄荷醇(0.8mM)可以通过跨膜流入或储存释放途径增加[Ca2 +] i。单独的(-)-薄荷醇中[Ca2 +] i的峰值增加为102.3±39nM(n = 3),1α,25(OH)2D3与(-)-薄荷醇的组合为124.5±51nM(n = 3)分别为[1]。 1α,25(OH)2D3与(-)-薄荷醇(0.8mM)的组合协同调节bcl-2和p21表达[1]。

[参考文献]

[1]. Park EJ, et al. Menthol Enhances an Antiproliferative Activity of 1alpha,25-Dihydroxyvitamin D(3) in LNCaP Cells. J Clin Biochem Nutr. 2009 Mar;44(2):125-30.

[相关活性小分子]

辣椒碱 | 辣椒平 | 5-(N-乙基-N-异丙基)阿米洛利 | 氯化二亚苯基碘鎓 | 2-(1,3-二甲基-2,6-二氧代-2,3-二氢-1H-嘌呤-7(6H)-基)-N-(4-异丙基苯基)乙酰胺 | 1-[2-(4-甲氧基)-2-[3-(4-甲氧基苯基)丙氧基]乙基]咪唑 | HC-067047 | AMG9810 | GSK1016790A | SAR7334 | PF-4840154 | RN-1734 | AMG 517 | 3-(4-氯苯基)-N-(3-甲氧基苯基)-2-丙烯酰胺 | 冰素

(-)-薄荷醇物理化学性质

[ 密度 ]:
0.9±0.1 g/cm3

[ 沸点 ]:
215.4±8.0 °C at 760 mmHg

[ 熔点 ]:
41-43ºC

[ 分子式 ]:
C₁₀H₂₀O

[ 分子量 ]:
156.265

[ 闪点 ]:
93.3±0.0 °C

[ 精确质量 ]:
156.151413

[ PSA ]:
20.23000

[ LogP ]:
3.20

[ 外观性状 ]:
白色晶体

[ 蒸汽压 ]:
0.0±0.9 mmHg at 25°C

[ 折射率 ]:
1.457

[ 储存条件 ]:
室温，干燥，密封

[ 水溶解性 ]:
insoluble

(-)-薄荷醇MSDS

详细MSDS(安全技术说明书)

(-)-薄荷醇毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OT0700000

CHEMICAL NAME :: l-Menthol

CAS REGISTRY NUMBER :: 2216-51-5

LAST UPDATED :: 199701

DATA ITEMS CITED :: 16

MOLECULAR FORMULA :: C10-H20-O

MOLECULAR WEIGHT :: 156.30

WISWESSER LINE NOTATION :: L6TJ AY1&1 DQ D1 -L

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3300 mg/kg

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

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 700 mg/kg

TOXIC EFFECTS :: Behavioral - general anesthetic Behavioral - altered sleep time (including change in righting reflex) Lungs, Thorax, or Respiration - respiratory depression

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1 gm/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3400 mg/kg

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

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6600 mg/kg

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

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 gm/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 800 mg/kg

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

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 800 mg/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 :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 34 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - respiratory depression

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >5 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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 2 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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 4 gm/kg

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

MUTATION DATA

TYPE OF TEST :: DNA repair

TEST SYSTEM :: Bacteria - Bacillus subtilis

DOSE/DURATION :: 10 mg/disc

REFERENCE :: OIGZDE Osaka-shi Igakkai Zasshi. Journal of Osaka City Medical Association. (Osaka-shi Igakkai, c/o Osaka-shiritsu Daigaku Igakubu, 1-4-54 Asahi-cho, Abeno-ku, Osaka, 545, Japan) V.24- 1975- Volume(issue)/page/year: 34,267,1985 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X6896 No. of Facilities: 499 (estimated) No. of Industries: 5 No. of Occupations: 27 No. of Employees: 43996 (estimated) No. of Female Employees: 34625 (estimated)

(-)-薄荷醇安全信息

[ 符号 ]:

GHS05, GHS07

[ 信号词 ]:
Danger

[ 危害声明 ]:
H315-H318-H335

[ 警示性声明 ]:
P261-P280-P305 + P351 + P338

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xi:Irritant

[ 风险声明 (欧洲) ]:
R36/37/38;R41

[ 安全声明 (欧洲) ]:
S26-S37/39

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
2

[ RTECS号 ]:
OT0700000

[ 海关编码 ]:
29061100

(-)-薄荷醇合成路线

详细合成路线

(-)-薄荷醇上下游产品

(-)-薄荷醇上游产品

(-)-薄荷醇下游产品

(-)-薄荷醇制备

薄荷醇可由天然薄荷原油提纯也可用合成法制取。唇形科植物薄荷的地上部分（茎；枝；叶和花序）经水蒸气蒸馏所得的精油称薄荷原油，得油率为0.5-0.6。合成薄合脑的方法有多种。1.从香茅醛中制造利用香茅醛易环化成异胡薄荷醇的性质，将右旋香茅醛用酸催化剂（如硅胶）环化成左旋异胡薄荷醇，分出左旋异胡薄荷醇，氢化生成左旋薄荷。其立体导师构体经热裂解可部分地遭到转变成右旋香茅醛，再循环使用。2.从百里酚中制造在间甲酚铝存在，对间甲酚进行烷基化反应生成百里酚。经催化加氢得所有四对薄荷醇立体异构体（即消旋薄荷醇；消旋新薄荷醇；消旋异薄荷醇和消旋新异薄荷醇）。将其进行蒸馏，取消旋薄荷醇馏分，制造酯后反复重结晶，进行异构体的分离和光学拆分。分离出来的左旋薄荷醇酯，经皂化后得薄荷脑。

(-)-薄荷醇海关

[ 海关编码 ]: 2906199090

[ 中文概述 ]:
2906199090. 其他环烷醇，环烯醇及环萜烯醇. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:5.5%. 普通关税:30.0%

[ 申报要素 ]: 品名, 成分含量, 用途

[ Summary ]:
2906199090. cyclanic, cyclenic or cyclotherpenic alcohols. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:5.5%. General tariff:30.0%

(-)-薄荷醇文献

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Surfactants, aromatic and isoprenoid compounds, and fatty acid biosynthesis inhibitors suppress Staphylococcus aureus production of toxic shock syndrome toxin 1.

Antimicrob. Agents Chemother. 53 , 1898-906, (2009)

Menstrual toxic shock syndrome is a rare but potentially life-threatening illness manifest through the actions of Staphylococcus aureus toxic shock syndrome toxin 1 (TSST-1). Previous studies have sho...

Effects of Menthol on Nicotine Pharmacokinetic, Pharmacology and Dependence in Mice.

PLoS ONE 10 , e0137070, (2015)

Although menthol, a common flavoring additive to cigarettes, has been found to impact the addictive properties of nicotine cigarettes in smokers little is known about its pharmacological and molecular...

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