芝麻酚

芝麻酚用途

【用途一】
用作抗氧剂、医药中间体及化妆品添加剂
【用途二】
广泛用于制备防霉抗菌剂、抗癌、抗高血压药品、高档洗发香波的头发调理剂等一系列精细化学品，是昂贵的化学、医药中间体原料，具有较好地开发利用价值和应用前景。还是抗癌药物和农药增效剂合成的重要中间体，还作为抗高血压和脑血管疾病药物的中间体。

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芝麻酚名称

[ CAS 号 ]:
533-31-3

[ 中文名 ]:
芝麻酚

[ 英文名 ]:
Sesamol

[中文别名 ]:

[英文别名 ]:

5-Benzodioxolol
MFCD00005827
5-Hydroxy-1,3-benzodioxole
EINECS 208-561-5
Phenol, 3,4- (methylenedioxy)-
Sesamol
4,5-methylenedioxyphenol
3,4-Methylenedioxyphenol
1-hydroxy-3,4-methylenedioxybenzene
4-hydroxy-1,2-methylenedioxy-benzene

芝麻酚生物活性

[ 描述 ]:

Sesamol 是芝麻油的主要成分,Sesamol 是一种自由基清除剂,在 DPPH 实验中,IC50 为 5.95±0.56 μg/mL。具有抗氧化活性[1]。抗肿瘤活性[2]。

[ 相关类别 ]:

信号通路 >> 其他 >> 其他

研究领域 >> 癌症

天然产物 >> 酚类

[体外研究]

Sesamol也被证明是脂质过氧化的经典抑制剂[1]。芝麻酚(0-1mM)有效诱导人肝细胞肝癌(HepG2)细胞凋亡。 Sesamol抑制细胞增殖并诱导HepG2细胞内在和外在的细胞凋亡。 Sesamol治疗通过诱导线粒体膜电位的丧失引发线粒体功能障碍。 Sesamol通过阻断PI3K III类/ Belin-1途径抑制线粒体自噬和自噬。 Sesamol降低抗凋亡蛋白Bcl-2的表达,但对凋亡信号Bax的表达没有影响。 Sesamol改善Fas/FasL的蛋白表达,并激活tBid和caspase-8,这些都参与了外源性凋亡途径[2]。

[体内研究]

Sesamol治疗35天对体重没有显着影响,尽管肿瘤体积受到显着抑制(与对照组相比,Sesamol在200mg/kg时的体积抑制率为40.56％)。然而,较低剂量(100mg/kg芝麻酚)仅在第一次治疗后27天具有显着的抗肿瘤生长作用。肿瘤组织中的Bcl-2/Bax比率也降低。此外,在Sesamol处理组中,细胞增殖标志物Ki76的水平下调,并且与对照相比,细胞凋亡标志物裂解的半胱天冬酶3的水平增加。 Sesamol以剂量依赖的方式显着降低LC3蛋白的表达[2]

[参考文献]

[1]. Kapadia GJ, et al. Chemopreventive effect of resveratrol, sesamol, sesame oil and sunflower oil in the Epstein-Barrvirus early antigen activation assay and the mouse skin two-stage carcinogenesis. Pharmacol Res. 2002 Jun;45(6):499-505.

[2]. Liu Z, et al. Sesamol Induces Human Hepatocellular Carcinoma Cells Apoptosis by Impairing MitochondrialFunction and Suppressing Autophagy. Sci Rep. 2017 Apr 4;7:45728.

[相关活性小分子]

芝麻酚物理化学性质

[ 密度 ]:
1.4±0.1 g/cm3

[ 沸点 ]:
274.0±29.0 °C at 760 mmHg

[ 熔点 ]:
62-65 °C(lit.)

[ 分子式 ]:
C₇H₆O₃

[ 分子量 ]:
138.121

[ 闪点 ]:
119.5±24.3 °C

[ 精确质量 ]:
138.031693

[ PSA ]:
38.69000

[ LogP ]:
1.52

[ 外观性状 ]:
白色至灰白色结晶粉末

[ 蒸汽压 ]:
0.0±0.6 mmHg at 25°C

[ 折射率 ]:
1.609

[ 储存条件 ]:
−20°C

[ 水溶解性 ]:
slightly soluble

芝麻酚MSDS

详细MSDS(安全技术说明书)

芝麻酚毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SM0890000

CHEMICAL NAME :: Phenol, 3,4-(methylenedioxy)-

CAS REGISTRY NUMBER :: 533-31-3

BEILSTEIN REFERENCE NO. :: 0127405

LAST UPDATED :: 199709

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C7-H6-O3

MOLECULAR WEIGHT :: 138.13

WISWESSER LINE NOTATION :: T56 BO DO CHJ GQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 874 gm/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors

REFERENCE :: JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.76- 1985- Volume(issue)/page/year: 83,1279,1992

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1092 gm/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors

REFERENCE :: JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.76- 1985- Volume(issue)/page/year: 83,1279,1992

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1612 gm/kg/96W-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors

REFERENCE :: JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.76- 1985- Volume(issue)/page/year: 81,207,1990

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1092 gm/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors

REFERENCE :: JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.76- 1985- Volume(issue)/page/year: 81,207,1990

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芝麻酚安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H315-H319-H335

[ 警示性声明 ]:
P261-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

[ 安全声明 (欧洲) ]:
S26-S36

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

[ WGK德国 ]:
3

[ RTECS号 ]:
SM0890000

[ 海关编码 ]:
2932999099

芝麻酚合成路线

详细合成路线

芝麻酚上下游产品

芝麻酚上游产品

芝麻酚下游产品

芝麻酚海关

[ 海关编码 ]: 2932999099

[ 中文概述 ]:
2932999099. 其他仅含氧杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

芝麻酚文献

Synthesis and photopolymerization kinetics of benzophenone sesamol one-component photoinitiator.

Photochem. Photobiol. Sci. 12(2) , 323-9, (2013)

A benzodioxole derivative, 4-(2-(benzodioxol-5-yloxy)ethoxy)benzophenone (BPC2BDO), based on 4-hydroxybenzophenone and sesamol was synthesized, and used as a one-component Type II photoinitiator. The ...

Comparison of the simple cyclic voltammetry (CV) and DPPH assays for the determination of antioxidant capacity of active principles.

Molecules 17(5) , 5126-38, (2012)

Antioxidant activity of a number of small (low molecular weight) natural compounds found in spices, condiments or drugs (gallic acid, sesamol, eugenol, thymol, carvacrol, vanillin, salicylaldehyde, li...

The interaction of sesamol with DNA and cytotoxicity, apoptosis, and localization in HepG2 cells.

Food Chem. 141(1) , 289-96, (2013)

Sesamol, a nutritional antioxidant phenolic compound present in sesame seed, has a potential therapeutic molecule effect against cancers. In this study, the interaction between sesamol and DNA was inv...

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芝麻酚