
Hydroquinone (ECMDB02434) (M2MDB000459)
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:56:44 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:12 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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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 E. coli arises from the catabolism of tyrosine and other similar aromatic substrates. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C6H6O2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 110.1106 Monoisotopic: 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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as hydroquinones. Hydroquinones 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 | Phenols | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Benzenediols | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 D-Alanine + Water + Quinone > Ammonium + Pyruvic acid + Hydroquinone 4 4,5-Dihydroorotic acid + Quinone <> Orotic acid + Hydroquinone L-Malic acid + Quinone <> Oxalacetic acid + Hydroquinone | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: |
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EcoCyc Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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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:
- frdA
- Uniprot ID:
- P00363
- Molecular weight:
- 65971
Reactions
Succinate + acceptor = fumarate + reduced acceptor. |
- 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
- Uniprot ID:
- P07014
- Molecular weight:
- 26770
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
- Uniprot ID:
- P09546
- Molecular weight:
- 143814
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
- Uniprot ID:
- P0A6J5
- Molecular weight:
- 47607
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
- Uniprot ID:
- P0A7E1
- Molecular weight:
- 36774
Reactions
(S)-dihydroorotate + a quinone = orotate + a quinol. |
- General function:
- Energy production and conversion
- Specific function:
- Seems to be involved in the anchoring of the catalytic components of the fumarate reductase complex to the cytoplasmic membrane
- Gene Name:
- frdC
- Uniprot ID:
- P0A8Q0
- Molecular weight:
- 15015
- General function:
- Involved in fumarate metabolic process
- Specific function:
- Seems to be involved in the anchoring of the catalytic components of the fumarate reductase complex to the cytoplasmic membrane
- Gene Name:
- frdD
- Uniprot ID:
- P0A8Q3
- Molecular weight:
- 13107
- 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
- Uniprot ID:
- P0AC41
- Molecular weight:
- 64421
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
- Uniprot ID:
- P0AC44
- Molecular weight:
- 12867
- 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:
- frdB
- Uniprot ID:
- P0AC47
- Molecular weight:
- 27123
Reactions
Succinate + acceptor = fumarate + reduced acceptor. |
- 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
- Uniprot ID:
- P0AFC3
- Molecular weight:
- 16457
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
- Uniprot ID:
- P0AFC7
- Molecular weight:
- 25056
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
- Uniprot ID:
- P0AFD1
- Molecular weight:
- 18590
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
- Uniprot ID:
- P0AFD4
- Molecular weight:
- 36219
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
- Uniprot ID:
- P0AFD6
- Molecular weight:
- 20538
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
- Uniprot ID:
- P0AFE0
- Molecular weight:
- 19874
Reactions
NADH + quinone = NAD(+) + quinol. |
- General function:
- Involved in oxidoreductase activity, acting on NADH or NADPH
- Specific function:
- There are 2 NADH dehydrogenases in E.coli, 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
- Uniprot ID:
- P0AFE4
- Molecular weight:
- 10845
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
- Uniprot ID:
- P0AFE8
- Molecular weight:
- 56524
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
- Uniprot ID:
- P0AFF0
- Molecular weight:
- 52044
Reactions
NADH + quinone = NAD(+) + quinol. |
- General function:
- Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
- Specific function:
- Can hydrolyze salicin and arbutin
- Gene Name:
- bglB
- Uniprot ID:
- P11988
- Molecular weight:
- 53161
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate. |
- General function:
- Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
- Specific function:
- Hydrolyzes a wide variety of P-beta-glucosides including cellobiose-6P, salicin-6P, arbutin-6P, gentiobiose-6P, methyl- beta-glucoside-6P and p-nitrophenyl-beta-D-glucopyranoside-6P. Is also able to hydrolyze phospho-N,N'-diacetylchitobiose
- Gene Name:
- chbF
- Uniprot ID:
- P17411
- Molecular weight:
- 50512
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate. |
- General function:
- Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
- Specific function:
- Can hydrolyze salicin, cellobiose, and probably arbutin
- Gene Name:
- ascB
- Uniprot ID:
- P24240
- Molecular weight:
- 53935
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate. |
- 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
- Uniprot ID:
- P31979
- Molecular weight:
- 49292
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
- Uniprot ID:
- P33599
- Molecular weight:
- 68236
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
- Uniprot ID:
- P33602
- Molecular weight:
- 100298
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
- Uniprot ID:
- P33607
- Molecular weight:
- 66438
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
- Uniprot ID:
- P33940
- Molecular weight:
- 60229
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
- Uniprot ID:
- P69054
- Molecular weight:
- 14299
- General function:
- Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
- Specific function:
- 6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate
- Gene Name:
- bglA
- Uniprot ID:
- Q46829
- Molecular weight:
- 55361
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate. |
- General function:
- Not Available
- Specific function:
- Not Available
- Gene Name:
- aes
- Uniprot ID:
- P23872
- Molecular weight:
- Not Available