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T3D0196 - ortho-Cresol
| Record Information | |
|---|---|
| Version | 1.0 |
| Creation Date | 2009-03-06 18:58:15 UTC |
| Update Date | 2013-04-25 08:33:14 UTC |
| Accession Number | T3D0196 |
| Identification | |
| Common Name | ortho-Cresol |
| Description | o-Cresol is an isomer of cresol. Cresols are organic methylphenol compounds that may occur naturally or be manufactured. Cresols have an odor characteristic to that of other simple phenols, reminiscent to some of a "medicine" smell. Cresols are used 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. (R835) |
| Compound Type |
|
| Chemical Structure |
|
| Synonyms |
|
| Chemical Formula | C7H8O |
| Average Molecular Weight | 108.1378 |
| Monoisotopic Molecular Weight | 108.057514878 |
| Chemical IUPAC Name | O-cresol |
| CAS Registry Number | 95-48-7 |
| SMILES | CC1=CC=CC=C1O |
| InChI Identifier | InChI=1S/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3 |
| InChI Key | InChIKey=QWVGKYWNOKOFNN-UHFFFAOYSA-N |
| Chemical Taxonomy | |
| Kingdom | Organic Compounds |
| Super Class | Benzenoids |
| Class | Benzene and Substituted Derivatives |
| Sub Class | Phenols and Derivatives |
| Direct Parent | Ortho Cresols |
| Alternative Parents |
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| Molecular Framework | Aromatic Homomonocyclic Compounds |
| Substituents |
|
| External Descriptors |
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| External Links | |
| DrugBank ID | Not Available |
| PubChem Compound ID | 335  |
| KEGG ID | C01542 |
| UniProt ID | Not Available |
| OMIM ID | Not Available |
| ChEBI ID | 28054 |
| BioCyc ID | CPD-109 |
| CTD ID | C034047 |
| Stitch ID | Cresol, ortho- |
| PDB ID | Not Available |
| ACToR ID | 1760 |
| Wikipedia Link | http://en.wikipedia.org/wiki/o-Cresol |
| Physical Properties | |
| Appearance | Colorless solids or liquids. |
| Melting Point | 29.8 C |
| Solubility | 25.9 mg/mL at 25 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)] |
| Predicted LogP | 2.1831018836666667 |
| Toxicity Profile | |
| Route of Exposure | Oral (R835) ; inhalation (R835) ; dermal (R835) |
| Mechanism of Action | 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. (R835) |
| 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. (R835, R836, R837, R839) |
| Toxicity Values | LD50: 344 mg/kg (Oral, Mouse) (R261) LD50: 179 mg/m3 (Inhalation, Mouse) (R261) LD50: 620 mg/kg (Dermal, Mouse) (R261) |
| Lethal Dose | Not Available |
| Carcinogenicity (IARC Classification) | Not Available |
| 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. (R835) |
| Minimum Risk Level | Intermediate Oral: 0.1 mg/kg/day (R260) Chronic Oral: 0.1 mg/kg/day (R260) |
| 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. (R782, R835) |
| 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. (R782) |
| 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. (R383) |
| References | |
| General References |
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Targets
1. Prostaglandin G/H synthase 1
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
o-Cresol inhibits prostaglandin G/H synthases, potentially affecting the cardiovascular system by suppressing blood clot formation and leading to tissue hemorrhage. (S198)UniProt ID: P23219
Gene: PTGS1
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
References:
- S198 — Chan CP, Yuan-Soon H, Wang YJ, Lan WH, Chen LI, Chen YJ, Lin BR, Chang MC, Jeng JH: Inhibition of cyclooxygenase activity, platelet aggregation and thromboxane B2 production by two environmental toxicants: m- and o-cresol. Toxicology. 2005 Mar 1;208(1):95-104.
[15664436 ]
2. Prostaglandin G/H synthase 2
May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity
o-Cresol inhibits prostaglandin G/H synthases, potentially affecting the cardiovascular system by suppressing blood clot formation and leading to tissue hemorrhage. (S198)UniProt ID: P35354
Gene: PTGS2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
References:
- S198 — Chan CP, Yuan-Soon H, Wang YJ, Lan WH, Chen LI, Chen YJ, Lin BR, Chang MC, Jeng JH: Inhibition of cyclooxygenase activity, platelet aggregation and thromboxane B2 production by two environmental toxicants: m- and o-cresol. Toxicology. 2005 Mar 1;208(1):95-104.
[15664436 ]