Hydroquinone (PAMDB000459)
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Version | 1.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 1/22/2018 11:54:54 AM | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Metabolite ID | PAMDB000459 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Hydroquinone | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description: | Hydroquinone, also benzene-1,4-diol, is an aromatic organic compound which is a type of phenol, having the chemical formula C6H4(OH)2. Its chemical structure has two hydroxyl groups bonded to a benzene ring in a para position. Hydroquinone is a white granular solid at room temperature and pressure. The hydroxyl groups of hydroquinone are quite weakly acidic. Hydroquinone can lose an H+ from one of the hydroxyls to form a monophenolate ion or lose an H+ from both to form a diphenolate ion. Hydroquinone has a variety of uses principally associated with its action as a reducing agent which is soluble in water. The presence of hydroquinone in Pseudomonas aeruginosa arises from the catabolism of tyrosine and other similar aromatic substrates. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C6H6O2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Average Molecular Weight: | 110.1106 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Monoisotopic Molecular Weight: | 110.036779436 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | QIGBRXMKCJKVMJ-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 123-31-9 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | benzene-1,4-diol | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | α-hydroquinone | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | OC1=CC=C(O)C=C1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Taxonomy Description | This compound belongs to the class of organic compounds known as hydroquinones. These are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Benzenoids | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Benzene and substituted derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Phenols and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Hydroquinones | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aromatic homomonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 172.3 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Arbutin 6-phosphate + Water > Glucose 6-phosphate + Hydroquinone L-Proline + Acceptor + Quinone <> L-D-1-Pyrroline-5-carboxylic acid + Reduced acceptor + (S)-1-pyrroline-5-carboxylate + Hydroquinone Arbutin 6-phosphate + Water <> Hydroquinone + beta-D-Glucose 6-phosphate 4-Hydroxyphenyl-4-hydroxybenzoate + Water <> 4-Hydroxybenzoic acid + Hydroquinone NADH + Quinone > NAD + Hydroquinone Succinic acid + Quinone <> Fumaric acid + Hydroquinone 4,5-Dihydroorotic acid + Quinone <> Orotic acid + Hydroquinone Formic acid + Quinone <> Carbon dioxide + Hydroquinone Glycerol 3-phosphate + Quinone <> Dihydroxyacetone phosphate + Hydroquinone NADH + NADPH + Hydrogen ion + Quinone <> NAD + NADP + Hydroquinone L-Malic acid + Quinone <> Oxalacetic acid + Hydroquinone L-Malic acid + Quinone + L-Malic acid > Oxalacetic acid + Hydroquinone | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Pathways: |
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Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: |
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References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Miyanohara, Isao; Yanagihara, Tadahisa. Hydroquinone. Jpn. Kokai Tokkyo Koho (1977), 4 pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in electron carrier activity
- Specific function:
- Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
- Gene Name:
- sdhB
- Locus Tag:
- PA1584
- Molecular weight:
- 26.2 kDa
Reactions
Succinate + acceptor = fumarate + reduced acceptor. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Oxidizes proline to glutamate for use as a carbon and nitrogen source and also function as a transcriptional repressor of the put operon
- Gene Name:
- putA
- Locus Tag:
- PA0782
- Molecular weight:
- 115.6 kDa
Reactions
L-proline + acceptor = (S)-1-pyrroline-5-carboxylate + reduced acceptor. |
(S)-1-pyrroline-5-carboxylate + NAD(P)(+) + 2 H(2)O = L-glutamate + NAD(P)H. |
- General function:
- Involved in D-amino-acid dehydrogenase activity
- Specific function:
- Oxidative deamination of D-amino acids
- Gene Name:
- dadA
- Locus Tag:
- PA5304
- Molecular weight:
- 47.1 kDa
Reactions
A D-amino acid + H(2)O + acceptor = a 2-oxo acid + NH(3) + reduced acceptor. |
- General function:
- Involved in catalytic activity
- Specific function:
- (S)-dihydroorotate + a quinone = orotate + a quinol
- Gene Name:
- pyrD
- Locus Tag:
- PA3050
- Molecular weight:
- 36.1 kDa
Reactions
(S)-dihydroorotate + a quinone = orotate + a quinol. |
- General function:
- Involved in electron carrier activity
- Specific function:
- Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
- Gene Name:
- sdhA
- Locus Tag:
- PA1583
- Molecular weight:
- 63.5 kDa
Reactions
Succinate + acceptor = fumarate + reduced acceptor. |
- General function:
- Involved in succinate dehydrogenase activity
- Specific function:
- Membrane-anchoring subunit of succinate dehydrogenase (SDH)
- Gene Name:
- sdhD
- Locus Tag:
- PA1582
- Molecular weight:
- 13.7 kDa
- General function:
- Involved in oxidoreductase activity, acting on NADH or NADPH
- Specific function:
- NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
- Gene Name:
- nuoA
- Locus Tag:
- PA2637
- Molecular weight:
- 15 kDa
Reactions
NADH + quinone = NAD(+) + quinol. |
- General function:
- Involved in NADH dehydrogenase (ubiquinone) activity
- Specific function:
- NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
- Gene Name:
- nuoB
- Locus Tag:
- PA2638
- Molecular weight:
- 25.4 kDa
Reactions
NADH + quinone = NAD(+) + quinol. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
- Gene Name:
- nuoE
- Locus Tag:
- PA2640
- Molecular weight:
- 18.1 kDa
Reactions
NADH + quinone = NAD(+) + quinol. |
- General function:
- Involved in oxidation-reduction process
- Specific function:
- NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient. This subunit may bind ubiquinone
- Gene Name:
- nuoH
- Locus Tag:
- PA2643
- Molecular weight:
- 36.7 kDa
Reactions
NADH + quinone = NAD(+) + quinol. |
- General function:
- Involved in electron carrier activity
- Specific function:
- NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
- Gene Name:
- nuoI
- Locus Tag:
- PA2644
- Molecular weight:
- 20.6 kDa
Reactions
NADH + quinone = NAD(+) + quinol. |
- General function:
- Involved in NADH dehydrogenase (ubiquinone) activity
- Specific function:
- NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
- Gene Name:
- nuoJ
- Locus Tag:
- PA2645
- Molecular weight:
- 17.6 kDa
Reactions
NADH + quinone = NAD(+) + quinol. |
- General function:
- Involved in oxidoreductase activity, acting on NADH or NADPH
- Specific function:
- There are 2 NADH dehydrogenases in Pseudomonas aeruginosa, however only this complex is able to use dNADH (reduced nicotinamide hypoxanthine dinucleotide, deamino-NADH) and dNADH-DB (dimethoxy- 5-methyl-6-decyl-1,4-benzoquinone) as substrates
- Gene Name:
- nuoK
- Locus Tag:
- PA2646
- Molecular weight:
- 11 kDa
Reactions
NADH + quinone = NAD(+) + quinol. |
- General function:
- Involved in NADH dehydrogenase (ubiquinone) activity
- Specific function:
- NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
- Gene Name:
- nuoM
- Locus Tag:
- PA2648
- Molecular weight:
- 55.7 kDa
Reactions
NADH + quinone = NAD(+) + quinol. |
- General function:
- Involved in NADH dehydrogenase (ubiquinone) activity
- Specific function:
- NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
- Gene Name:
- nuoN
- Locus Tag:
- PA2649
- Molecular weight:
- 51.7 kDa
Reactions
NADH + quinone = NAD(+) + quinol. |
- General function:
- Involved in NADH dehydrogenase (ubiquinone) activity
- Specific function:
- NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
- Gene Name:
- nuoF
- Locus Tag:
- PA2641
- Molecular weight:
- 48.7 kDa
Reactions
NADH + quinone = NAD(+) + quinol. |
- General function:
- Involved in oxidoreductase activity, acting on NADH or NADPH
- Specific function:
- NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
- Gene Name:
- nuoC
- Locus Tag:
- PA2639
- Molecular weight:
- 68.3 kDa
Reactions
NADH + quinone = NAD(+) + quinol. |
- General function:
- Involved in electron carrier activity
- Specific function:
- NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
- Gene Name:
- nuoG
- Locus Tag:
- PA2642
- Molecular weight:
- 99 kDa
Reactions
NADH + quinone = NAD(+) + quinol. |
- General function:
- Involved in NADH dehydrogenase (ubiquinone) activity
- Specific function:
- NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
- Gene Name:
- nuoL
- Locus Tag:
- PA2647
- Molecular weight:
- 66.2 kDa
Reactions
NADH + quinone = NAD(+) + quinol. |
- General function:
- Involved in malate dehydrogenase (quinone) activity
- Specific function:
- (S)-malate + a quinone = oxaloacetate + reduced quinone
- Gene Name:
- mqo
- Locus Tag:
- PA3452
- Molecular weight:
- 57.2 kDa
Reactions
(S)-malate + a quinone = oxaloacetate + reduced quinone. |
- General function:
- Involved in succinate dehydrogenase activity
- Specific function:
- Membrane-anchoring subunit of succinate dehydrogenase (SDH)
- Gene Name:
- sdhC
- Locus Tag:
- PA1581
- Molecular weight:
- 13.7 kDa