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WordNet
- a toxic white lustrous crystalline phenol used to treat certain skin diseases and as a photographic developer (同)pyrogallic acid
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2012/04/21 07:52:44」(JST)
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Pyrogallol |
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Other names
1,2,3-Trihydroxybenzene
Pyrogallic acid
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Identifiers |
CAS number |
87-66-1 Y |
ChemSpider |
13835557 Y |
UNII |
01Y4A2QXY0 Y |
ChEBI |
CHEBI:16164 Y |
ChEMBL |
CHEMBL307145 Y |
Jmol-3D images |
Image 1 |
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InChI=1S/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H Y
Key: WQGWDDDVZFFDIG-UHFFFAOYSA-N Y
InChI=1/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H
Key: WQGWDDDVZFFDIG-UHFFFAOYAT
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Properties |
Molecular formula |
C6H6O3 |
Molar mass |
126.11 g/mol |
Density |
1.45 g/cm3 |
Melting point |
131–134 °C
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Boiling point |
309 °C
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Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
Infobox references |
Pyrogallol or benzene-1,2,3-triol is a benzenetriol.
Contents
- 1 Natural occurrences
- 2 Chemistry
- 3 Uses
- 4 See also
- 5 References
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Natural occurrences
The aquatic plant Myriophyllum spicatum produces pyrogallic acid.[1]
Chemistry
It is a white crystalline powder and a powerful reducing agent. It was first prepared by Scheele 1786 by heating gallic acid. An alternate preparation is heating para-chlorophenoldisulphonic acid with potassium hydroxide.
When in alkaline solution, it absorbs oxygen from the air, turning purple from a colourless solution. It can be used in this way to calculate the amount of oxygen in air, notably via the use of the Orsat apparatus.
Uses
One can find its uses in hair dying, dying of suturing materials and for oxygen absorption in gas analysis. It also has antiseptic properties. Pyrogallol was also used as a developing agent in black-and-white developers, but its use is largely historical except for special purpose applications. (Hydroquinone is more commonly used today.)
Harmful if swallowed and repeated or prolonged exposure to this compound is not recommended. Pyrogallol is not likely to be used as a modern hair dye due to the suspected toxicity of the compound. [2]
Use in photography
Though a popular photographic developing agent in the 19th and early 20th centuries, pyrogallol largely fell out of favor around the 1920s, though still used by a few notable photographers including Edward Weston. In those days it had a reputation for erratic and unreliable behavior, due possibly to its propensity for oxidation. It experienced a revival starting in the 1980s due largely to the efforts of experimenters Gordon Hutchings and John Wimberley. Hutchings spent over a decade working on pyrogallol formulas, eventually producing one he named PMK (for its main ingredients, pyrogallol, Metol, and Kodalk [trade name of Kodak for sodium metaborate]). This formulation resolved the consistency issues, and Hutchings found that an interaction between the greenish stain given to film by pyro developers and the color sensitivity of modern variable-contrast photographic papers gave the effect of an extreme compensating developer. From 1969 to 1977, Wimberley experimented with the Pyrogallol developing agent. He published his formula for WD2D in 1977 in Petersons Photographic.
PMK and other modern pyro formulations are now used by many black-and-white photographers.
See also
- Gallic acid
- Catechol
- Gallacetophenone (2,3,4-trihydroxyacetophenone)
References
- ^ Myriophyllum spicatum-released allelopathic polyphenols inhibiting growth of blue-green algae Microcystis aeruginosa. Satoshi Nakai, Yutaka Inoue, Masaaki Hosomi and Akihiko Murakami, Water Research, Volume 34, Issue 11, 1 August 2000, Pages 3026–3032, doi:10.1016/S0043-1354(00)00039-7
- ^ Safety data for 1,2,3-trihydroxybenzene
English Journal
- Antimicrobial and antioxidant activities of Mimusops elengi seed extract mediated isotropic silver nanoparticles.
- Kiran Kumar HA1, Mandal BK2, Mohan Kumar K1, Maddinedi Sb1, Sai Kumar T1, Madhiyazhagan P3, Ghosh AR3.
- Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2014 Sep 15;130:13-8. doi: 10.1016/j.saa.2014.03.024. Epub 2014 Apr 5.
- The present study reports the use of Mimusops elengi (M. elengi) fruit extract for the synthesis of silver nanoparticles (Ag NPs). The synthesized Ag NPs was initially noticed through visual color change from yellow to reddish brown and further confirmed by surface plasmonic resonance (SPR) band at
- PMID 24759779
- Preparative isolation and purification of phlorotannins from Ecklonia cava using centrifugal partition chromatography by one-step.
- Lee JH1, Ko JY1, Oh JY1, Kim CY2, Lee HJ3, Kim J4, Jeon YJ5.
- Food chemistry.Food Chem.2014 Sep 1;158:433-7. doi: 10.1016/j.foodchem.2014.02.112. Epub 2014 Feb 28.
- Various bioactive phlorotannins of Ecklonia cava (e.g., dieckol, eckol, 6,6-bieckol, phloroglucinol, phloroeckol, and phlorofucofuroeckol-A) are reported. However, their isolation and purification are not easy. Centrifugal partition chromatography (CPC) can be used to efficiently purify the various
- PMID 24731366
- Salivary α-amylase, serum albumin, and myoglobin protect against DNA-damaging activities of ingested dietary agents in vitro.
- Hossain MZ1, Patel K1, Kern SE2.
- Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.Food Chem Toxicol.2014 Aug;70:114-9. doi: 10.1016/j.fct.2014.05.002. Epub 2014 May 16.
- Potent DNA-damaging activities were seen in vitro from dietary chemicals found in coffee, tea, and liquid smoke. A survey of tea varieties confirmed genotoxic activity to be widespread. Constituent pyrogallol-like polyphenols (PLPs) such as epigallocatechin-3-gallate (EGCG), pyrogallol, and gallic a
- PMID 24842839
Japanese Journal
- 抗酸化物質のスーパーオキシド消去能とガルビノキシル法またはDPPH法で測定した抗酸化能との相関
- 戸早 裕美子,落合 爲一
- 日本食品化学学会誌 20(1), 61-65, 2013-04-22
- 11種の抗酸化物質(AH)のスーパーオキシドアニオンの消去能を求め、それ等とDPPHおよびガルビノキシルラジカルに対する反応性とを比較した。スーパーオキシドアニオンはキサンチン/キサンチンオキシダーゼ系で発生させた。スーパーオキシドアニオンのプローブとして4-[3-(4-ヨードフェニル)-2-(4-ニトロフェニル)-2H-5-テトラゾリオ]-1,3-ベンゼンジスルホン酸ナトリウム塩(WST-1)を …
- NAID 110009603498
- Accelerated Degradation of Exogenous Indole by Burkholderia unamae Strain CK43B Exposed to Pyrogallol-Type Polyphenols
- KIM Dongyeop,RAHMAN Atiqur,SITEPU Irnayuli R.,HASHIDOKO Yasuyuki
- Bioscience, Biotechnology, and Biochemistry, 2013
- … Pyrogallol also showed a cometabolic effect on decarboxylation-coupled oxidative deamination of B. … These results suggest that pyrogallol-type plant polyphenols act as stimulators on B. …
- NAID 130003361193
- Transformation of tea catechins and flavonoid glycosides by treatment with Japanese post-fermented tea acetone powder
- Tanaka Takashi,Umeki Hirotaka,Nagai Sachi,Shii Takuya,Matsuo Yosuke,Kouno Isao
- Food Chemistry 134(1), 276-281, 2012-09-01
- … Under aerobic conditions, EGCg was hydrolysed to EGC and gallic acid, which were further converted to gallocatechin (GC) and pyrogallol, respectively. … Gallic acid was degraded to pyrogallol and then further decomposed. …
- NAID 80022496892
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