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Details

Stereochemistry ACHIRAL
Molecular Formula C6H6O3
Molecular Weight 126.11
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYROGALLOL

SMILES

OC1=CC=CC(O)=C1O

InChI

InChIKey=WQGWDDDVZFFDIG-UHFFFAOYSA-N
InChI=1S/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H

HIDE SMILES / InChI
Molecular Formula C6H6O3
Molecular Weight 126.11
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

1921
1468
Doses

Doses

DosePopulationAdverse events​
10 % 1 times / day multiple, topical
Dose: 10 %, 1 times / day
Route: topical
Route: multiple
Dose: 10 %, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3835960
unhealthy, 77 years
Health Status: unhealthy
Age Group: 77 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/3835960
Disc. AE: Squamous cell carcinoma...
AEs leading to
discontinuation/dose reduction:
Squamous cell carcinoma
Sources:
https://pubmed.ncbi.nlm.nih.gov/3835960
10 g single, topical
Dose: 10 g
Route: topical
Route: single
Dose: 10 g
Sources:
https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/pyrogallol_508.pdf
unknown
Health Status: unknown
Sources:
https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/pyrogallol_508.pdf
Other AEs: Adverse event...
Other AEs:
Adverse event (grade 5)
Sources:
https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/pyrogallol_508.pdf
AEs

AEs

AESignificanceDosePopulation
Squamous cell carcinoma Disc. AE
10 % 1 times / day multiple, topical
Dose: 10 %, 1 times / day
Route: topical
Route: multiple
Dose: 10 %, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3835960
unhealthy, 77 years
Health Status: unhealthy
Age Group: 77 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/3835960
Adverse event grade 5
10 g single, topical
Dose: 10 g
Route: topical
Route: single
Dose: 10 g
Sources:
https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/pyrogallol_508.pdf
unknown
Health Status: unknown
Sources:
https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/pyrogallol_508.pdf
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:16164
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16164
ChemicalBook
CB6107909
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6107909
eMolecules
484215
https://www.emolecules.com/cgi-bin/more?vid=484215
MolPort
MolPort-001-786-773
https://www.molport.com/shop/molecule-link/MolPort-001-786-773
ZINC
ZINC000000330141
http://zinc15.docking.org/substances/ZINC000000330141
PubMed

PubMed

TitleDatePubMed
High glucose impairs superoxide production from isolated blood neutrophils.
2003-04
Roles of human liver cytochrome P450 3A4 and 1A2 enzymes in the oxidation of myristicin.
2003-02-03
Ketamine and midazolam differentially inhibit nonadrenergic noncholinergic lower esophageal sphincter relaxation in rabbits: role of superoxide anion and nitric oxide synthase.
2003-02
[The determination of total concentration and activity of antioxidants in foodstuffs].
2003-01-17
Metabolic activation of 3-hydroxyanisole by isolated rat hepatocytes.
2003-01-06
Structural insights into ligand interactions at the acetylcholinesterase peripheral anionic site.
2003-01-02
Oxidative stress, NO* and smooth muscle cell extracellular superoxide dismutase expression.
2003-01-02
Method for analysis of tannic acid and its metabolites in biological samples: application to tannic acid metabolism in the rat.
2003-01-01
Antioxidant activity and characterization of volatile constituents of Taheebo (Tabebuia impetiginosa Martius ex DC).
2003-01-01
Cell permeable ROS scavengers, Tiron and Tempol, rescue PC12 cell death caused by pyrogallol or hypoxia/reoxygenation.
2003-01
Adsorption and detection of some phenolic compounds by rice husk ash of Kenyan origin.
2002-12
Contractile responses to reactive oxygen species in the canine basilar artery in vitro: selective inhibitory effect of MCI-186, a new hydroxyl radical scavenger.
2002-12
Detection of low-molecular-weight proteins in urine by dipsticks.
2002-12
O2(-)-mediated impairment of coronary arterial relaxation is prevented by overnight treatment with 1 nM beta-estradiol.
2002-12
Flow-injection spectrophotometric determination of periodate and iodate by their reaction with pyrogallol red in acidic media.
2002-11
Screening of ubiquitous plant constituents for COX-2 inhibition with a scintillation proximity based assay.
2002-11
Purification and characterization of an extracellular laccase from the edible mushroom Lentinula edodes, and decolorization of chemically different dyes.
2002-11
Purification and characterization of soluble peroxidase from oil palm (Elaeis guineensis Jacq) leaf.
2002-11
The preparation and characterization of an antimicrobial polypeptide from the loach, Misgurnus anguillicaudatus.
2002-11
Pyrogallol-induced hepatotoxicity in rats: a model to evaluate antioxidant hepatoprotective agents.
2002-10
Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells.
2002-10
Replacement of active-site cysteine-436 by serine converts cytochrome P450 2B4 into an NADPH oxidase with negligible monooxygenase activity.
2002-09-20
Activity-guided fractionation of green tea extract with antiproliferative activity against human stomach cancer cells.
2002-09
Ab initio study of the mechanism of singlet-dioxygen addition to hydroxyaromatic compounds: negative evidence for the involvement of peroxa and endoperoxide intermediates.
2002-08
Effect of drying method on the volatiles in bay leaf (Laurus nobilis L.).
2002-07-31
Engineering the proximal heme cavity of catalase-peroxidase.
2002-07-25
Aroma biosynthesis in strawberry: s-adenosylmethionine:furaneol o-methyltransferase activity in ripening fruits.
2002-07-03
Chemical stress-responsive genes from the lignin-degrading fungus Phanerochaete chrysosporium exposed to dibenzo-p-dioxin.
2002-07-02
Identification of pyrogallol as an antiproliferative compound present in extracts from the medicinal plant Emblica officinalis: effects on in vitro cell growth of human tumor cell lines.
2002-07
Antioxidant activity of dodecyl gallate.
2002-06-05
Kinetic-spectrophotometric determination of palladium in hydrogenation catalyst by its catalytic effect on the oxidation of pyrogallol red by hydrogen peroxide.
2002-06
Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity.
2002-06
Deoxygenation of polyhydroxybenzenes: an alternative strategy for the benzene-free synthesis of aromatic chemicals.
2002-05-29
A reassessment of the peroxynitrite scavenging activity of uric acid.
2002-05
Isolation from a shea cake digester of a tannin-degrading Streptococcus gallolyticus strain that decarboxylates protocatechuic and hydroxycinnamic acids, and emendation of the species.
2002-05
The effect of oxidative stress on endothelium-dependent and nitric oxide donor-induced relaxation: implications for nitrate tolerance.
2002-05
Production of interleukin-6 by skeletal myotubes: role of reactive oxygen species.
2002-05
Isolation, identification, and characterization of compounds from acer rubrum capable of oxidizing equine erythrocytes.
2002-04
Diphenol activation of the monophenolase and diphenolase activities of field bean (Dolichos lablab) polyphenol oxidase.
2002-03-13
Selective detection of o-diphenols on copper-plated screen-printed electrodes.
2002-03-01
Evaluation of antioxidant properties of root bark of Hemidesmus indicus R. Br. (Anantmul).
2002-03
Physiological activity of some aminophosphonates.
2002-02-12
Blood copper concentrations and cuproenzyme activities in a colony of cats.
2002
Catechol- and pyrogallol-type flavonoids. Analysis of tea catechins in plasma.
2002
Superoxide dismutase activities of spermatozoa and seminal plasma are not correlated with male infertility.
2002
Superoxide dismutase kinetics.
2002
Hydrogen-bonded molecular capsules are stable in polar media.
2001-11-21
Reversal of pyrogallol-induced delay in gastric emptying in rats by ginger (Zingiber officinale).
2001-11
Measurement of dissolved oxygen based on enhanced cerium(IV) chemiluminescence.
2001-01
Asaricin, the main component of Ocotea opifera Mart. essential oil.
2001
Patents

Patents

03948952
2
03968070
1
04015017
1
04056625
2
04172960
2
04781941
1
05399613
1
05691428
2
06472190
1
07585891
1
07919534
2
08591957
2
JP2000273063A
1
JP2002003317A
1
JP2003261847A
1
JP2009525747A
2
JP2009531331A
6
JP4795440B2
15
JP5322220B2
3
JPH01102456A
1
JPH01104065A
1
JPH01294713A
1
JPH01319411A
1
JPH02188520A
1
JPH03102354A
1
JPH0317008A
1
JPH03174445A
1
JPH0454142A
3
JPH05201895A
1
JPH05295090A
1
JPH06183958A
1
JPH07118192A
1
JPH07228607A
2
JPH1160534A
1
JPS51113812A
1
JPS5554034A
1
JPS5554305A
1
JPS56131380A
1
JPS56151492A
1
JPS5646830A
1
JPS5653465A
1
JPS57102971A
1
JPS57129695A
1
JPS5750932A
1
JPS5778469A
1
JPS5853903A
3
JPS59129207A
1
JPS61247709A
1
JPS6197240A
1
JPS62138508A
1
JPS62236804A
1
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:53:39 GMT 2025
Edited
by admin
on Mon Mar 31 17:53:39 GMT 2025
Record UNII
01Y4A2QXY0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYROGALLOL
HSDB   INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
NSC-5035
Preferred Name English
PYROGALLOL [MI]
Common Name English
PYROGALLOL [MART.]
Common Name English
PYROGALLOL [HSDB]
Common Name English
PYROGALLOL [VANDF]
Common Name English
PYROGALLIC ACID
Common Name English
Pyrogallol [WHO-DD]
Common Name English
1,2,3-TRIHYDROXYBENZENE
Systematic Name English
Code System Code Type Description
NCI_THESAURUS
C80909
Created by admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
PRIMARY
CAS
87-66-1
Created by admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
PRIMARY
SMS_ID
100000078934
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
MESH
D011748
Created by admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-762-9
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
FDA UNII
01Y4A2QXY0
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
CHEBI
16164
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
MERCK INDEX
m9382
Created by admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
Pyrogallol
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
EPA CompTox
DTXSID6025983
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
CONCEPT Industrial Aid
PUBCHEM
1057
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
ChEMBL
CHEMBL307145
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
RXCUI
9022
Created by admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
PRIMARY RxNorm
EVMPD
SUB15064MIG
Created by admin on Mon Mar 31 17:53:39 GMT 2025 , Edited by admin on Mon Mar 31 17:53:39 GMT 2025
PRIMARY
NSC
5035
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
HSDB
794
Created by admin on Mon Mar 31 17:53:40 GMT 2025 , Edited by admin on Mon Mar 31 17:53:40 GMT 2025
PRIMARY
Related Record Type Details
STEVIA REBAUDIANA LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
Pyrogallol content for water extract of plant leaf was 951.27+/-1.12 and plant callus was 40.72+/-0.44 expressed as mg/100 g of dry base of extract. For the analysis of phenolic acids, a Nova pack C18 UG120 equipped with a Guard column, a JASCO HPLC system consisting of a column oven, a UV-Vis diode array detector set at 280 nm, a Liquid chromatography pump and a ChromNAV software program were used.
ALCHEMILLA MONTICOLA WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
AGRIMONIA EUPATORIA FLOWERING TOP
PARENT -> CONSTITUENT ALWAYS PRESENT
NIH
NCATS
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