o-CRESOL
Relevant Data
Food Additives Approved in the United States
Flavouring Substances Approved by European Union:
General Information
| Synonyms: | o-CRESYLIC ACID, 1-HYDROXY-2-METHYLBENZENE, o-HYDROXYTOLUENE, o-METHYLPHENOL |
| Chemical Names: | o-CRESOL |
| CAS number: | 95-48-7 |
| COE number: | 618 |
| JECFA number: | 691 |
| FEMA number: | 3480 |
| Functional Class: |
Flavouring Agent FLAVOURING_AGENT |
From apps.who.int
Evaluations
| Evaluation year: | 2000 |
| ADI: | No safety concern at current levels of intake when used as a flavouring agent |
| Report: | TRS 901-JECFA 55/44 |
| Tox Monograph: | FAS 46-JECFA 55/165 |
| Specification: | COMPENDIUM ADDENDUM 8/FNP 52 Add.8/166 |
From apps.who.int
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 335 |
| IUPAC Name | 2-methylphenol |
| InChI | InChI=1S/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3 |
| InChI Key | QWVGKYWNOKOFNN-UHFFFAOYSA-N |
| Canonical SMILES | CC1=CC=CC=C1O |
| Molecular Formula | C7H8O |
| Wikipedia | orthocresol |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 108.14 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 70.8 |
| CACTVS Substructure Key Fingerprint | A A A D c c B g I A A A A A A A A A A A A A A A A A A A A A A A A A A w A A A A A A A A A A A B A A A A G g A A C A A A D A S A m A A y B o A A A g C A A i B C A A A C A A A g I A A I i A A G C I g I J i K C E R K A c A A k w B E I m A e A w C A O A A A A A A A I A A A A A A A A A B A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 20.2 |
| Monoisotopic Mass | 108.058 |
| Exact Mass | 108.058 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 8 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9345 |
| Human Intestinal Absorption | HIA+ | 0.9957 |
| Caco-2 Permeability | Caco2+ | 0.9333 |
| P-glycoprotein Substrate | Non-substrate | 0.7462 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9619 |
| Non-inhibitor | 0.9929 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8793 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8471 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7091 |
| CYP450 2D6 Substrate | Non-substrate | 0.6969 |
| CYP450 3A4 Substrate | Non-substrate | 0.7025 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6617 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9203 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9683 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8627 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9506 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7616 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8313 |
| Non-inhibitor | 0.9398 | |
| AMES Toxicity | Non AMES toxic | 0.9235 |
| Carcinogens | Non-carcinogens | 0.7948 |
| Fish Toxicity | High FHMT | 0.7532 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9046 |
| Honey Bee Toxicity | High HBT | 0.7832 |
| Biodegradation | Ready biodegradable | 0.5758 |
| Acute Oral Toxicity | II | 0.7686 |
| Carcinogenicity (Three-class) | Non-required | 0.6000 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.6538 | LogS |
| Caco-2 Permeability | 1.7130 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.7739 | LD50, mol/kg |
| Fish Toxicity | 1.0399 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.1649 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | Oral ; inhalation ; dermal |
|---|---|
| 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. |
| 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. |
| Toxicity Values | LD50: 344 mg/kg (Oral, Mouse) LD50: 179 mg/m3 (Inhalation, Mouse) LD50: 620 mg/kg (Dermal, Mouse) |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | Intermediate Oral: 0.1 mg/kg/day Chronic Oral: 0.1 mg/kg/day |
| 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. (L482, L528) |
| 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. |
| Reference |
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From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Phenols |
| Subclass | Cresols |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Ortho cresols |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| 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 |
| Description | This compound 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. |
From ClassyFire
Targets
- Specific Function:
- Keratin-binding protein required for epithelial cell polarization. Involved in apical junction complex (AJC) assembly via its interaction with PARD3. Required for ciliogenesis.
- Gene Name:
- FBF1
- Uniprot ID:
- Q8TES7
- Molecular Weight:
- 125445.19 Da
References
- Ogata N, Shibata T: Binding of alkyl- and alkoxy-substituted simple phenolic compounds to human serum proteins. Res Commun Mol Pathol Pharmacol. 2000;107(1-2):167-73. [11334365 ]
- General Function:
- Prostaglandin-endoperoxide synthase activity
- Specific Function:
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells.
- Gene Name:
- PTGS1
- Uniprot ID:
- P23219
- Molecular Weight:
- 68685.82 Da
References
- 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 ]
- General Function:
- Prostaglandin-endoperoxide synthase activity
- Specific Function:
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, phenotypic changes, resistance to apoptosis and tumor angiogenesis. In cancer cells, PTGS2 is a key step in the production of prostaglandin E2 (PGE2), which plays important roles in modulating motility, proliferation and resistance to apoptosis.
- Gene Name:
- PTGS2
- Uniprot ID:
- P35354
- Molecular Weight:
- 68995.625 Da
References
- 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 ]
From T3DB