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桧木醇

桧木醇用途

Hinokitiol 是从日本扁柏中分离到的挥发油成分,能够降低 Nrf2 的表达,减少 DNMT1 和 UHRF1 的 mRNA 和蛋白的表达,具有抗感染、抗氧化及抗肿瘤等活性。

桧木醇名称

[ CAS 号 ]:
499-44-5

[ 中文名 ]:
桧木醇

[ 英文名 ]:
Hinokitiol

[中文别名 ]:

[英文别名 ]:

Isopropyltropolone
B-THUJAPLICIN
beta-thujaplicin
4-ISOPROPYLTROPOLONE
MFCD00040180
2-Hydroxy-4-isopropylcyclohepta-2,4,6-trien-1-one
β-Thujaplicine
EINECS 207-880-7
Hinokitiol
β-Thujaplicin

桧木醇生物活性

[ 描述 ]:

Hinokitiol 是从日本扁柏中分离到的挥发油成分,能够降低 Nrf2 的表达,减少 DNMT1 和 UHRF1 的 mRNA 和蛋白的表达,具有抗感染、抗氧化及抗肿瘤等活性。

[ 相关类别 ]:

信号通路 >> 表观遗传学 >> DNA甲基转移酶

信号通路 >> NF-κB信号通路 >> KEAP1-Nrf2

天然产物 >> 萜类化合物和糖苷

研究领域 >> 癌症

研究领域 >> 感染

[ 靶点 ]

DNMT1

Nrf2

[体外研究]

在U87MG和T98G神经胶质瘤细胞系中,日扁柏醇显示出活力的剂量依赖性降低,IC50值分别为316.5±35.5和152.5±25.3μM。 Hinokitiol抑制胶质瘤干细胞中的ALDH活性和自我更新能力,并抑制体外致癌性。 Hinokitiol还以剂量依赖的方式降低神经胶质瘤干细胞中Nrf2的表达[1]。 Hinokitiol(0-100μM)以剂量和时间依赖性方式抑制结肠癌细胞生长。 Hinokitiol(5,10μM)降低DNMT1和UHRF1 mRNA和蛋白质表达,并通过增强HCT-116细胞中的5hmC水平来增加TET1表达。此外,日扁柏醇降低甲基化状态并恢复MGMT,CHST10和BTG4基因的mRNA表达[2]。

[细胞实验]

U87MG和T98G神经胶质瘤细胞在含有10％胎牛血清的Ham's F12培养基（DMEM / F-12）的Dulbecco改良的Eagle培养基中培养。使用MTT测定细胞活力以评估日扁柏醇的细胞毒性。在各种浓度的日扁柏醇或载体存在下，在37℃下将细胞接种于24孔板（1×10 5细胞/孔）中24小时，然后与MTT试剂一起温育。将活细胞的蓝色甲crystals晶体溶解在DMSO中，然后在570nm下用分光光度法评价。 DMSO处理组设定为100％，数据表示为DMSO对照的百分比。 IC50值由GraFit软件计算。

[参考文献]

[1]. Ouyang WC, et al. Hinokitiol suppresses cancer stemness and oncogenicity in glioma stem cells by Nrf2 regulation. Cancer Chemother Pharmacol. 2017 Aug;80(2):411-419.

[2]. Seo JS, et al. Hinokitiol induces DNA demethylation via DNMT1 and UHRF1 inhibition in colon cancer cells. BMC Cell Biol. 2017 Feb 27;18(1):14.

[相关活性小分子]

桧木醇物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
303.4±35.0 °C at 760 mmHg

[ 熔点 ]:
50-52 °C(lit.)

[ 分子式 ]:
C₁₀H₁₂O₂

[ 分子量 ]:
164.201

[ 闪点 ]:
128.1±18.5 °C

[ 精确质量 ]:
164.083725

[ PSA ]:
37.30000

[ LogP ]:
1.89

[ 外观性状 ]:
固体;White to Light yellow powder to crystal

[ 蒸汽压 ]:
0.0±1.4 mmHg at 25°C

[ 折射率 ]:
1.554

[ 储存条件 ]:
室温

[ 水溶解性 ]:
水溶性：实际上不溶；可溶于：乙醚,醇

桧木醇MSDS

详细MSDS(安全技术说明书)

桧木醇毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GU4200000

CHEMICAL NAME :: 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-isopropyl-

CAS REGISTRY NUMBER :: 499-44-5

BEILSTEIN REFERENCE NO. :: 2045206

LAST UPDATED :: 199710

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C10-H12-O2

MOLECULAR WEIGHT :: 164.22

WISWESSER LINE NOTATION :: L7VJ BQ DY1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - food intake (animal) Gastrointestinal - other changes

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: OTS0570591

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 85 mg/kg

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

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 6,755,1963

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 541 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - analgesia Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 91,550,1971

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 128 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - analgesia Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 91,550,1971

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - food intake (animal)

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: OTS0570591

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 500 mg/kg

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

REFERENCE :: JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 48,722,1959

桧木醇安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H302

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

[ 危害码 (欧洲) ]:
Xn:Harmful;

[ 风险声明 (欧洲) ]:
R22

[ 安全声明 (欧洲) ]:
S36

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

[ WGK德国 ]:
3

[ RTECS号 ]:
GU4200000

[ 海关编码 ]:
2914400090

桧木醇合成路线

详细合成路线

桧木醇上下游产品

桧木醇上游产品

桧木醇下游产品

桧木醇制备

存在于日本扁柏（Chamaecyparis obtuse Sieb.et Zucc.）的木材中，由萃取而得。

桧木醇海关

[ 海关编码 ]: 2914400090

[ 中文概述 ]:
2914400090 其他酮醇及酮醛。监管条件:无。增值税率:17.0%。退税率:9.0%。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, 丙酮报明包装

[ Summary ]:
2914400090 other ketone-alcohols and ketone-aldehydes。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

桧木醇文献

Determination of hinokitiol in skin lotion by high-performance liquid chromatography-ultraviolet detection after precolumn derivatization with 4-fluoro-7-nitro-2,1,3-benzoxadiazole.

J. Cosmet. Sci. 64(5) , 381-9, (2013)

Hinokitiol, a potent, broad-spectrum antibacterial agent, is a component of various personal care products. In this study, the concentration of hinokitiol in skin lotion was analyzed by means of high-...

The furan route to tropolones: probing the antiproliferative effects of β-thujaplicin analogs.

Org. Biomol. Chem. 10(43) , 8597-604, (2012)

A direct route to analogs of the naturally occurring tropolone β-thujaplicin has been developed in just four steps from furan. Using this method, a series of derivatives were synthesized and evaluated...

High-performance liquid chromatography with dual-wavelength ultraviolet detection for measurement of hinokitiol in personal care products.

J. Cosmet. Sci. 60(5) , 519-25, (2009)

Hinokitiol is found in the heartwood of several cupressaceous plants and is frequently added to cosmetic products such as hair restorers, skin lotions, and body soaps because of its potent and broad-s...

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桧木醇