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1,2,3-苯三酚

1,2,3-苯三酚用途

Pyrogallol 是一种多酚化合物,具有抗真菌和抗牛皮癣的特性。邻苯三酚是一种还原剂,能够产生自由基,特别是超氧阴离子。

1,2,3-苯三酚名称

[ CAS 号 ]:
87-66-1

[ 中文名 ]:
邻苯三酚

[ 英文名 ]:
Pyrogallol

[中文别名 ]:

[英文别名 ]:

1,2,3-trishydroxybenzene
trihydroxybenzene
1,2,3-Trihydroxybenzene
EINECS 201-762-9
Pyrogallol
PYROGALL
MFCD00008358
benzene-1,2,3-triol
Fourrine 85
Benzol-1,2,3-triol

1,2,3-苯三酚生物活性

[ 描述 ]:

Pyrogallol 是一种多酚化合物,具有抗真菌和抗牛皮癣的特性。邻苯三酚是一种还原剂,能够产生自由基,特别是超氧阴离子。

[ 相关类别 ]:

信号通路 >> 抗感染 >> 真菌

研究领域 >> 感染

天然产物 >> 酚类

[ 靶点 ]

Human Endogenous Metabolite

[体外研究]

邻苯三酚(PG)是一种还原剂,能够产生自由基,特别是超氧阴离子(O2•-),因此经常被用作照相显影剂和染发工业。邻苯三酚通过细胞凋亡和谷胱甘肽(GSH)的消耗抑制Calu-6和A549肺癌细胞生长。邻苯三酚(PG)通过过量产生O2•诱导肺癌细胞凋亡,并影响这些细胞中丝裂原活化蛋白激酶(MAPKs)[1]。研究了邻苯三酚对人肺成纤维细胞(HPF)细胞活力和坏死细胞死亡的影响。对于这些实验,使用0,50或100μM邻苯三酚来区分具有或不具有给定MAPK抑制剂的细胞活力抑制或死亡水平。用50和100μM邻苯三酚处理分别在24小时时将HPF活力降低~40％和65％。用MEK抑制剂治疗在50μM邻苯三酚处理的HPF细胞中略微增强细胞活力的抑制,而用p38抑制剂处理则温和地减弱了活力的抑制。在100μM邻苯三酚处理的HPF细胞中,所有MAPK抑制剂在一定程度上增加了生存力的抑制,单独用p38抑制剂处理可增强HPF对照细胞活力。通过测量细胞的乳酸脱氢酶(LDH)释放来确定坏死细胞死亡。虽然用50μM邻苯三酚处理不影响HPF细胞的LDH释放,但100μM邻苯三酚显着增加LDH释放[1]。

[细胞实验]

简而言之，将96孔微量滴定板中的每孔5×103 HPF细胞暴露于0,50或100μM邻苯三酚，有或没有各MAPK抑制剂，在37℃下24小时。通过测量MTT确定邻苯三酚和/或给定MAPK抑制剂诱导的细胞活力的变化;染料吸光度[1]。

[参考文献]

[1]. Han BR, et al. MAPK inhibitors enhance cell death in pyrogallol-treated human pulmonary fibroblast cells via increasing O₂^•- levels. Oncol Lett. 2017 Jul;14(1):1179-1185.

[相关活性小分子]

1,2,3-苯三酚物理化学性质

[ 密度 ]:
1.453

[ 沸点 ]:
309 ºC

[ 熔点 ]:
131-135 ºC

[ 分子式 ]:
C₆H₆O₃

[ 分子量 ]:
126.110

[ 闪点 ]:
164.3±16.9 °C

[ 精确质量 ]:
126.031693

[ PSA ]:
60.69000

[ LogP ]:
0.29

[ 外观性状 ]:
无气味的白色至灰色固体

[ 蒸汽密度 ]:
4.4 (vs air)

[ 蒸汽压 ]:
0.0±0.6 mmHg at 25°C

[ 折射率 ]:
1.677

[ 储存条件 ]:
Desiccate at RT

[ 稳定性 ]:
Stability Stable, but decolourises in light. Combustible. Incompatible with strong oxidising agents, alkalies, metal oxides, ammonia, antipyrine, phenol, iodine, lime water, menthol, potassium permanganate, strong bases.

[ 水溶解性 ]:
400 g/L (25 ºC)

1,2,3-苯三酚MSDS

详细MSDS(安全技术说明书)

1,2,3-苯三酚毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UX2800000

CHEMICAL NAME :: Pyrogallol

CAS REGISTRY NUMBER :: 87-66-1

BEILSTEIN REFERENCE NO. :: 0907431

LAST UPDATED :: 199806

DATA ITEMS CITED :: 37

MOLECULAR FORMULA :: C6-H6-O3

MOLECULAR WEIGHT :: 126.12

WISWESSER LINE NOTATION :: QR BQ CQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 28 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - other changes

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 120 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - excitement Gastrointestinal - changes in structure or function of salivary glands

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 650 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 :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 300 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 :: 400 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 :: 566 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 :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 25 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 :: Subcutaneous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 300 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 - dog

DOSE/DURATION :: 80 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 :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1600 mg/kg

TOXIC EFFECTS :: Gastrointestinal - gastritis Lungs, Thorax, or Respiration - chronic pulmonary edema

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

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 :: Amphibian - frog

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - miosis (pupillary constriction) Behavioral - muscle weakness Behavioral - ataxia

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - wild bird species

DOSE/DURATION :: 75 mg/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 98 gm/kg/4W-I

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3950 mg/kg/58W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - tumors at site of application

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3 gm/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 5 mg/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Rodent - hamster Lung

DOSE/DURATION :: 25 umol/L

REFERENCE :: EVHPAZ EHP, Environmental Health Perspectives. (U.S. Government Printing Office, Supt of Documents, Washington, DC 20402) No.1- 1972- Volume(issue)/page/year: 82,81,1989 *** REVIEWS *** TOXICOLOGY REVIEW MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 47,75,1978 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 81963 No. of Facilities: 848 (estimated) No. of Industries: 22 No. of Occupations: 25 No. of Employees: 19191 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 81963 No. of Facilities: 2175 (estimated) No. of Industries: 8 No. of Occupations: 14 No. of Employees: 38038 (estimated) No. of Female Employees: 24931 (estimated)

1,2,3-苯三酚安全信息

[ 符号 ]:

GHS07, GHS08

[ 信号词 ]:
Warning

[ 危害声明 ]:
H315-H319-H341-H412

[ 警示性声明 ]:
P280-P305 + P351 + P338

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

[ 危害码 (欧洲) ]:
Xn:Harmful

[ 风险声明 (欧洲) ]:
R20/21/22;R52/53;R68

[ 安全声明 (欧洲) ]:
S22-S24/25-S61-S36/37

[ 危险品运输编码 ]:
UN 2811 6.1/PG 3

[ WGK德国 ]:
3

[ RTECS号 ]:
UX2800000

[ 包装等级 ]:
III

[ 危险类别 ]:
6.1

[ 海关编码 ]:
2907299090

1,2,3-苯三酚合成路线

详细合成路线

1,2,3-苯三酚上下游产品

1,2,3-苯三酚上游产品

1,2,3-苯三酚下游产品

1,2,3-苯三酚制备

1.将没食子酸和水加入高压釜中，于200-210℃脱羧0.5h，经脱色、过滤、蒸发制得成品，或用真空升华进行精制。

2.以没食子酸为原料，采用一种有机碱性化合物为催化剂，常压下控制温度180 ～ 190℃，进行脱羟反应：

当反应物中不再放出二氧化碳气体，表示反应已达终点。所得焦性没食子酸粗品依次采用减压干燥和真空升华进行提纯。
3.以环已稀为原料，环烷酸钒等为催化剂，于70～150℃下进行氧化反应制得2,3-环氧环己醇，然后于109℃下，以甲醇为溶剂，与过量水行水合反应，所得1,2,3-环己三醇，在Pd-c催化作用下于液相或气相惰气保护下脱氢，制得质量较好的焦性没食子酸。
过程反应式如下：

焦性没食子酸的制备方法中，除使用基础化学品（环己酮、环己三醇、间苯二酚等）为原料的化学合成法外，大都以没食子单宁或其初级产品为原料，其制备方法又可分为两步法和一步法两种。没食子酸一步法直接使用含没食子单宁的天然物，在同一反应介质和容器中，同时进行水解和脱羧反应，制得焦性没食子酸。因而一步法较两步法的制备步骤大大缩短，操作简单，生产周期较短。工艺步骤如下：将塔拉粉（主成分为没食子单宁，干基含量50%～60%）置于耐压应器中，加入适量的水搅匀，再将氧化钙溶于水而成的氢氧化钙乳液加入反应器中，充分搅匀，加盖密封，置于可控温的恒温烘中缓缓升温，当温度升至160～220℃时，保温1～4h。反应完毕后降至室温，开盖倾出反应液，缓慢加入浓盐酸（或浓硫酸）调至酸性，同时搅拌排除二氧化碳。过滤去渣，滤液适当浓缩后用乙酸乙酯萃取，酯层减压蒸干。残留物用二甲苯热提取，经冷却、结晶、过滤，得浅米黄色焦性没食子酸晶体。如将此产品用二甲苯作两次处理，并用活性炭脱色，则可得到近白色的焦性没食子酸针状晶体。优化的反应条件：塔拉粉与水的配比1∶3，氧化钙用量是塔拉粉量的15%～25%，反应温度200℃，反应时间3h。

4. 由棓酸经加热失去二氧化碳而制得。

1,2,3-苯三酚海关

[ 海关编码 ]: 2907299090

[ 中文概述 ]:
2907299090 其他多元酚，酚醇。监管条件:AB(入境货物通关单,出境货物通关单)。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

[ 监管条件 ]: A.入境货物通关单 B.出境货物通关单

[ 检验检疫 ]: R.进口食品卫生监督检验 S.出口食品卫生监督检验 M.进口商品检验 N.出口商品检验

[ Summary ]:
2907299090 polyphenols; phenol-alcohols。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:5.5%。general tariff:30.0%

1,2,3-苯三酚文献

Biotransformation and nitroglycerin-induced effects on antioxidative defense system in rat erythrocytes and reticulocytes.

Gen. Physiol. Biophys. 33(4) , 393-401, (2014)

The effects of nitroglycerin (glyceryl trinitrate - GTN) are mediated by liberated nitric oxide (NO) and formed reactive nitrogen species, which induces oxidative stress during biotransformation in re...

Degradation of anti-inflammatory drug ketoprofen by electro-oxidation: comparison of electro-Fenton and anodic oxidation processes.

Environ. Sci. Pollut. Res. Int. 21(14) , 8406-16, (2014)

The electrochemical degradation of the nonsteroidal anti-inflammatory drug ketoprofen in tap water has been studied using electro-Fenton (EF) and anodic oxidation (AO) processes with platinium (Pt) an...

Characterization of arsenic-induced cytotoxicity in liver with stress in erythrocytes and its reversibility with Pleurotus florida lectin.

Toxicol. Ind. Health 31(2) , 108-22, (2015)

Arsenic is one of the most hazardous substances in the environment known to cause toxicity in multiple organs. Cell adhesion, morphological alterations, cell proliferation, terminal deoxyuridine triph...

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