| Record Information |
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| Version | 2.0 |
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| Creation Date | 2009-03-06 18:58:15 UTC |
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| Update Date | 2014-12-24 20:21:19 UTC |
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| Accession Number | T3D0196 |
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| Identification |
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| Common Name | o-Cresol |
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| Class | Small Molecule |
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| Description | o-Cresol is a minor urinary metabolite of toluene, a widely used chemical with neurotoxicological properties. (3). o-Cresol is used commercially as a disinfectant. Exposure may occur by inhalation, by cutaneous adsorption or by oral ingestion. o-Cresol denature and precipitate cellular proteins and thus may rapidly cause poisoning. o-Cresol is metabolized by conjugation and oxidation. Ingestion of o-Cresol cause intense burning of mouth and throat, followed by marked abdominal pain and distress. The minimum lethal dose of cresol by mouth is about 2 g. (4). |
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| Compound Type | - Aromatic Hydrocarbon
- Disinfectant
- Food Toxin
- Household Toxin
- Industrial/Workplace Toxin
- Metabolite
- Natural Compound
- Organic Compound
- Pollutant
- Solvent
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| Chemical Structure | |
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| Synonyms | | Synonym | | 1-Hydroxy-2-methylbenzene | | 1-Methyl-2-hydroxybenzene | | 2-Cresol | | 2-Hydroxytoluene | | 2-Methylphenol | | O-Cresol | | o-Cresylic acid | | o-Hydroxytoluene | | o-Methylphenol | | o-Methylphenylol | | o-Oxytoluene | | o-Toluol | | ortho-Cresylic acid | | ortho-Hydroxytoluene | | ortho-Methylphenol | | ortho-Methylphenylol | | ortho-Oxytoluene | | ortho-Toluol |
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| Chemical Formula | C7H8O |
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| Average Molecular Mass | 108.138 g/mol |
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| Monoisotopic Mass | 108.058 g/mol |
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| CAS Registry Number | 95-48-7 |
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| IUPAC Name | 2-methylphenol |
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| Traditional Name | o-cresol |
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| SMILES | CC1=CC=CC=C1O |
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| InChI Identifier | InChI=1S/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3 |
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| InChI Key | InChIKey=QWVGKYWNOKOFNN-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as ortho cresols. These are organic compounds containing an ortho-cresol moiety, which consists of a benzene bearing one hydroxyl group at ring positions 1 and 2, respectively. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Phenols |
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| Sub Class | Cresols |
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| Direct Parent | Ortho cresols |
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| Alternative Parents | |
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| Substituents | - O-cresol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Toluene
- Monocyclic benzene moiety
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Endogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | Colorless solids or liquids. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 29.8°C | | Boiling Point | 191.5°C (376.7°F) | | Solubility | 25.9 mg/mL at 25°C | | LogP | 1.95 |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a6r-9600000000-5a01d451557a1b35332a | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0pbi-9200000000-be9e6e56af8374e66beb | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a4i-7900000000-c8eb63e9fe9da99fda0f | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00ko-5900000000-cef3087dea0c431cce4b | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a6r-9600000000-5a01d451557a1b35332a | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0pbi-9200000000-be9e6e56af8374e66beb | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a4i-7900000000-c8eb63e9fe9da99fda0f | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00ko-5900000000-cef3087dea0c431cce4b | JSpectraViewer | MoNA | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-6900000000-7ba7c816e0edce6b772f | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-06di-7900000000-db9d20fae81c588496fe | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0a4i-5900000000-c7d0037b6de77737b7e4 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0006-9000000000-151af99851311002a3fa | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-03y3-9000000000-260e2bcf6f7dca1a3c9c | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive | splash10-0a6r-9600000000-ac87a40c538d227b6915 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive | splash10-0pbi-9200000000-be9e6e56af8374e66beb | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-0a4i-7900000000-1a7cfac9452c2b14f977 | JSpectraViewer | MoNA | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0900000000-5d6424b7db2e7e40d6d7 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-2900000000-e468ad1b8f28b32d7276 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ufr-9000000000-2629c90f57b18d57c59d | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-8feea1e7288d5bc80ea5 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0900000000-22006f43be347c915292 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a6u-9300000000-d3ec19098100f79d4ebd | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-3f09649991cc4cfcf1ec | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0900000000-3f09649991cc4cfcf1ec | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0i03-9100000000-267c04454ade05650a34 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-2900000000-c580eec1345db0ab9045 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002f-9000000000-923877cbbb5c2a1edb9c | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-016u-9000000000-09eba92f6442b1a88ad5 | JSpectraViewer | | MS | Mass Spectrum (Electron Ionization) | splash10-0a4i-9800000000-c390212681445a7e2727 | JSpectraViewer | MoNA | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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| Toxicity Profile |
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| Route of Exposure | Oral (9) ; inhalation (9) ; dermal (9) |
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| Mechanism of Toxicity | Target organs of ingested cresols in humans are the blood, kidneys, lungs, liver, heart, and central nervous system. Cresols impair the stratum corneum and produce coagulation necrosis by denaturating and precipitating proteins. They may also induce changes in neurotransmitter levels, affect the activities of some enzymes, increase lipid peroxidation, and change membrane fluidity in the brain. (9) |
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| Metabolism | Cresols can be absorbed following inhalation, oral, and dermal exposure. Once in the body they can distribute rapidly into many organs and tissues. Cresols undergo oxidative metabolism in the liver and are rapidly eliminated, mostly in the urine, as sulfate or glucuronide conjugates. The activation of cresols by oxidation involves tyrosinase and thyroid peroxidase, forming a reactive quinone methide. Experiments with recombinant P-450s demonstrated cresol metabolism was mediated by several P-450s including CYP2D6, 2C19, 1A2, 1A1, and 2E1. (9, 1, 10, 2) |
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| Toxicity Values | LD50: 344 mg/kg (Oral, Mouse) (5)
LD50: 179 mg/m3 (Inhalation, Mouse) (5)
LD50: 620 mg/kg (Dermal, Mouse) (5) |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Cresols are used to as solvents, disinfectants and deodorizers, as well as to make other chemicals. They may be formed normally in the body from other compounds. Cresols are found in many foods and in wood and tobacco smoke, crude oil, coal tar, and in chemical mixtures used as wood preservatives. Small organisms in soil and water produce cresols when they break down materials in the environment. Breathing air containing cresols is the primary source of exposure. Exposure may also result from drinking contaminated water, eating contaminated food and coming into contact with liquids containing cresols. (9) |
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| Minimum Risk Level | Intermediate Oral: 0.1 mg/kg/day (7)
Chronic Oral: 0.1 mg/kg/day (7) |
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| Health Effects | Cresols breathed, ingested, or applied to the skin at very high levels can be very harmful because they are corrosive substances. Ingestion of high levels results in mouth and throat burns, abdominal pain, vomiting, kidney problems, and effects on the blood and nervous system. Skin contact with high levels of cresols can burn the skin and damage the kidneys, liver, blood, lungs, and brain. Tachycardia, respiratory failure, unconsciousness and death may occur in both cases. Many of these effects may not by caused directly by cresols, but may be a result of secondary reactions to shock caused by external and internal burns. (8, 9) |
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| Symptoms | Ingestion of cresols results in burning of the mouth and throat, abdominal pain, and vomiting. Inhalation or dermal exposure to cresols can produce irritation and corrosion at the site of contact. (8) |
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| Treatment | Following oral exposure, immediately dilute with 4 to 8 ounces (120 to 240 mL) of water or milk (not to exceed 4 ounces/120 mL in a child). Observe patients with ingestion carefully for the possible development of esophageal or gastrointestinal tract irritation or burns. If signs or symptoms of esophageal irritation or burns are present, consider endoscopy to determine the extent of injury. In case of hypotension, infuse isotonic fluid. If hypotension persists, administer dopamine or norepinephrine. In case of hypertension, monitor vital signs regularly. For mild/moderate asymptomatic hypertension (no end organ damage), pharmacologic treatment is generally not necessary. Following inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of acute lung injury, maintain ventilation and oxygenation and evaluate with frequent arterial blood gas or pulse oximetry monitoring. Early use of PEEP and mechanical ventilation may be needed. Following eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. (6) |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB02055 |
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| PubChem Compound ID | 335 |
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| ChEMBL ID | CHEMBL46931 |
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| ChemSpider ID | 13835772 |
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| KEGG ID | C01542 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | 28054 |
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| BioCyc ID | CPD-109 |
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| CTD ID | C034047 |
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| Stitch ID | Cresol, ortho- |
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| PDB ID | JZ0 |
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| ACToR ID | 1760 |
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| Wikipedia Link | o-Cresol |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Link |
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| General References | - Yan Z, Zhong HM, Maher N, Torres R, Leo GC, Caldwell GW, Huebert N: Bioactivation of 4-methylphenol (p-cresol) via cytochrome P450-mediated aromatic oxidation in human liver microsomes. Drug Metab Dispos. 2005 Dec;33(12):1867-76. Epub 2005 Sep 20. [16174805 ]
- Yokoi H, Belfort G: High-rate membrane supported aqueous-phase enzymatic conversion in organic solvent. Bioseparation. 1994 Jun;4(3):213-20. [7765181 ]
- Fustinoni S, Mercadante R, Campo L, Scibetta L, Valla C, Foa V: Determination of urinary ortho- and meta-cresol in humans by headspace SPME gas chromatography/mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Mar 25;817(2):309-17. [15687000 ]
- Boatto G, Nieddu M, Carta A, Pau A, Lorenzoni S, Manconi P, Serra D: Determination of phenol and o-cresol by GC/MS in a fatal poisoning case. Forensic Sci Int. 2004 Jan 28;139(2-3):191-4. [15040915 ]
- Lewis RJ Sr. (ed) (2004). Sax's Dangerous Properties of Industrial Materials. 11th Edition. Hoboken, NJ: Wiley-Interscience, Wiley & Sons, Inc.
- Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
- ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- International Programme on Chemical Safety (IPCS) INCHEM (1996). Poison Information Monograph for Cresols. [Link]
- ATSDR - Agency for Toxic Substances and Disease Registry (2008). Toxicological profile for cresols. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- Wikipedia. Sodium dichromate. Last Updated 25 May 2009. [Link]
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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