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Pyrogallol

Names

[ CAS No. ]:
87-66-1

[ Name ]:
Pyrogallol

[Synonym ]:
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
pyrogallic
1,2,3-Benzenetriol
gallol
Piral
1,2,3-trihydroxy-benzene
Fourrine PG
Phloroglucinol Impurity 1

Biological Activity

[Description]:

Pyrogallol is a polyphenol compound, which has anti-fungal and anti-psoriatic properties. Pyrogallol is a reductant that is able to generate free radicals, in particular superoxide anions.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Fungal
Research Areas >> Infection
Natural Products >> Phenols

[Target]

Human Endogenous Metabolite


[In Vitro]

Pyrogallol (PG) is a reductant that is able to generate free radicals, in particular superoxide anions (O2•-), so has frequently been used as a photographic developing agent and in the hair dying industry. Pyrogallol inhibits Calu-6 and A549 lung cancer cell growth via apoptosis and depletion of glutathione (GSH). Pyrogallol (PG) induces apoptosis in lung cancer cells via the overproduction of O2•- and affects mitogen activated protein kinases (MAPKs) in these cells[1]. The effect of Pyrogallol on human pulmonary fibroblast (HPF) cell viability and necrotic cell death is examined. For these experiments, 0, 50 or 100 µM Pyrogallol is used to differentiate the levels of cell viability inhibition or death with or without a given MAPK inhibitor. Treatment with 50 and 100 µM Pyrogallol decreases HPF viability by ~40 and 65% at 24 h, respectively. Treatment with an MEK inhibitor slightly enhances the inhibition of cell viability in 50 µM Pyrogallol-treated HPF cells, whereas treatment with a p38 inhibitor mildly attenuates the inhibition of viability. In 100 µM Pyrogallol-treated HPF cells, all the MAPK inhibitors increase the inhibition of viability to a certain extent, with treatment with the p38 inhibitor alone augmenting HPF control cell viability. Necrotic cell death is determined by measuring lactate dehydrogenase (LDH) release from cells. While treatment with 50 µM Pyrogallol does not affect LDH release from HPF cells, 100 µM Pyrogallol significantly increases LDH release[1].

[Cell Assay]

Briefly, 5×103 HPF cells per well in 96-well microtiter plates are exposed to 0, 50 or 100 µM Pyrogallol with or without each MAPK inhibitor at 37°C for 24 h. Changes in cell viability induced by Pyrogallol and/or a given MAPK inhibitor are determined by measuring the MTT; dye absorbance[1].

[References]

[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.


[Related Small Molecules]

Cycloheximide | 3-Methyladenine | Hydrocortisone | Acetylcysteine(N-acetylcysteine) | Hygromycin B | Retinoic acid | Melatonine | Dinoprostone | Nicotinamide | Adenosine triphosphate | 4-Acetamidophenol | Prostaglandin E1 | Dehydroepiandrosterone | Corticosterone | Progesterone

Chemical & Physical Properties

[ Density]:
1.453

[ Boiling Point ]:
309 ºC

[ Melting Point ]:
131-135 ºC

[ Molecular Formula ]:
C6H6O3

[ Molecular Weight ]:
126.110

[ Flash Point ]:
164.3±16.9 °C

[ Exact Mass ]:
126.031693

[ PSA ]:
60.69000

[ LogP ]:
0.29

[ Vapour density ]:
4.4 (vs air)

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.677

[ Storage condition ]:
Desiccate at RT

[ Stability ]:
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.

[ Water Solubility ]:
400 g/L (25 ºC)

MSDS

Toxicological Information

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)

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H341-H412

[ Precautionary Statements ]:
P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
Faceshields;full-face respirator (US);Gloves;Goggles;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R20/21/22;R52/53;R68

[ Safety Phrases ]:
S22-S24/25-S61-S36/37

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
UX2800000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1

[ HS Code ]:
2907299090

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2907299090

[ 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%

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