4-chloro-3-methyl phenol

4-chloro-3-methylphenol

CAS: 59-50-7 C7 H7 Cl O MW: 142.58399000

Identification

Name4-chloro-3-methyl phenol
IUPAC4-chloro-3-methylphenol
CAS Number59-50-7
EINECS200-431-6
FDA UNII36W53O7109
Molecular FormulaC7 H7 Cl O
Molecular Weight142.58399000
MDL NumberMFCD00002323
Nikkaji NumberJ4.604C
Beilstein1237629
XlogP33.10 (est)

Regulatory

FDA/DG SANTE Petitions, Reviews, NoticesFCN 560
FDA Mainterm (IAUFC)59-50-7 ; 4-CHLORO-3-METHYLPHENOL
FDA RegulationFDA PART 175 -- INDIRECT FOOD ADDITIVES: ADHESIVES AND COMPONENTS OF COATINGS

Physical Properties

Appearance pinkish to white crystalline solid (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 67.00 °C. @ 760.00 mm Hg
Boiling Point 235.00 °C. @ 760.00 mm Hg
Vapor Pressure 0.050000 mmHg @ 20.00 °C. (est)
Flash Point 200.00 °F. TCC ( 93.40 °C. ) (est)
logP (o/w) 3.100
Soluble in water, 699.3 mg/L @ 25 °C (est)

Cosmetic Information

CosIngcosmetic data
Cosmetic Usespreservatives

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintravenous-mouse LD50 70 mg/kg
Dermal Toxicitysubcutaneous-mouse LD50 360 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorypreservatives
Recommendation for 4-chloro-3-methyl phenol usage levels up tonot for fragrance use.
Recommendation for 4-chloro-3-methyl phenol flavor usage levels up tonot for flavor use.

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Potential Uses

preservatives

Natural Occurrence

not found in nature

Synonyms

aptal baktol candaseptic 4- chloro-3-methylphenol 2- chloro-5-hydroxytoluene 4- chloro-m-cresol p- chloro-m-cresol 4- chloro-meta-cresol para- chloro-meta-cresol p- chlorocresol parmatol parol PCMC peritonan phenol, 4-chloro-3-methyl- PubMed: In situ derivatization combined to automated microextraction by packed sorbents for the determination of chlorophenols in soil samples by gas chromatography mass spectrometry. PubMed: Ammonium Increases Ca(2+) Signalling and Up-Regulates Expression of TRPC1 Gene in Astrocytes in Primary Cultures and in the In Vivo Brain. PubMed: Functional characterisation of the R2452W ryanodine receptor variant associated with malignant hyperthermia susceptibility. PubMed: The ryanodine receptor agonist 4-chloro-3-ethylphenol blocks ORAI store-operated channels. PubMed: Functional characterization of 2 known ryanodine receptor mutations causing malignant hyperthermia. PubMed: Capabilities and limitations of dispersive liquid-liquid microextraction with solidification of floating organic drop for the extraction of organic pollutants from water samples. PubMed: Skeletal muscle-specific T-tubule protein STAC3 mediates voltage-induced Ca2+ release and contractility. PubMed: Skeletal muscle ryanodine receptor mutations associated with malignant hyperthermia showed enhanced intensity and sensitivity to triggering drugs when expressed in human embryonic kidney cells. PubMed: Ligand-dependent conformational changes in the clamp region of the cardiac ryanodine receptor. PubMed: Contact and fumigant toxicities of 3-methylphenol isolated from Ostericum koreanum and its derivatives against house dust mites. PubMed: Sequence capture and massively parallel sequencing to detect mutations associated with malignant hyperthermia. PubMed: Molecular structure, spectroscopic studies (FTIR, FT-Raman and NMR) and HOMO-LUMO analysis of 6-chloro-o-cresol and 4-chloro-3-methyl phenol by density functional theoretical study. PubMed: The Anx7(+/-) knockout mutation alters electrical and secretory responses to Ca(2+)-mobilizing agents in pancreatic β-cells. PubMed: The antioxidant N-acetylcysteine prevents the mitochondrial fragmentation induced by soluble amyloid-β peptide oligomers. PubMed: Residual sarcoplasmic reticulum Ca2+ concentration after Ca2+ release in skeletal myofibers from young adult and old mice. PubMed: Mutated p.4894 RyR1 function related to malignant hyperthermia and congenital neuromuscular disease with uniform type 1 fiber (CNMDU1). PubMed: Ryanodine receptors are expressed in epidermal keratinocytes and associated with keratinocyte differentiation and epidermal permeability barrier homeostasis. PubMed: Analysis of human cultured myotubes responses mediated by ryanodine receptor 1. PubMed: Alterations of excitation-contraction coupling and excitation coupled Ca(2+) entry in human myotubes carrying CAV3 mutations linked to rippling muscle. PubMed: Muscle weakness in Ryr1I4895T/WT knock-in mice as a result of reduced ryanodine receptor Ca2+ ion permeation and release from the sarcoplasmic reticulum. PubMed: Quantitative measurement of Ca²(+) in the sarcoplasmic reticulum lumen of mammalian skeletal muscle. PubMed: Lymphocyte-based determination of susceptibility to malignant hyperthermia: a pilot study in swine. PubMed: In vitro dermal penetration of 4-chloro-3-methylphenol from commercial metal working fluid and aqueous vehicles. PubMed: Combined moxidectin and environmental therapy do not eliminate Chorioptes bovis infestation in heavily feathered horses. PubMed: Functional studies of RYR1 mutations in the skeletal muscle ryanodine receptor using human RYR1 complementary DNA. PubMed: Functional properties of RYR1 mutations identified in Swedish patients with malignant hyperthermia and central core disease. PubMed: Sarcoplasmic reticulum Ca2+ depletion in adult skeletal muscle fibres measured with the biosensor D1ER. PubMed: Determination of water pollutants by direct-immersion solid-phase microextraction using polymeric ionic liquid coatings. PubMed: Commonly used ryanodine receptor activator, 4-chloro-m-cresol (4CmC), is also an inhibitor of SERCA Ca2+ pumps. PubMed: A ryanodine receptor agonist promotes the consolidation of long-term memory in young chicks. PubMed: Functional analysis of ryanodine receptor type 1 p.R2508C mutation in exon 47. PubMed: Simultaneous recording of intramembrane charge movement components and calcium release in wild-type and S100A1-/- muscle fibres. PubMed: Evaluation of irritancy and sensitization potential of metalworking fluid mixtures and components. PubMed: Effects of plasticizers and their mixtures on estrogen receptor and thyroid hormone functions. PubMed: Factors affecting SOCE activation in mammalian skeletal muscle fibers. PubMed: Functional characterization of ryanodine receptor (RYR1) sequence variants using a metabolic assay in immortalized B-lymphocytes. PubMed: [Disturbances in the function of cardiomyocyte ryanodine receptors of spontaneously hypertensive rats revealed by 4-chloro-m-cresol]. PubMed: Use of a programmed temperature vaporizer and an in situ derivatization reaction to improve sensitivity in headspace-gas chromatography. Application to the analysis of chlorophenols in water. PubMed: Functional ryanodine receptors in the plasma membrane of RINm5F pancreatic beta-cells. PubMed: Amperometric determination of chloroguaiacol at submicromolar levels after on-line preconcentration with molecularly imprinted polymers. PubMed: Detection of phenolic compounds in flow systems based on tyrosinase-modified reticulated vitreous carbon electrodes. PubMed: Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography. PubMed: Novel ryanodine receptor mutation that may cause malignant hyperthermia. PubMed: Altered stored calcium release in skeletal myotubes deficient of triadin and junctin. PubMed: Faster and simpler determination of chlorophenols in water by fiber introduction mass spectrometry. PubMed: Wide-ranging genomic effects of plasticisers and related compounds. PubMed: Heterogeneous gene expression and functional activity of ryanodine receptors in resistance and conduit pulmonary as well as mesenteric artery smooth muscle cells. PubMed: Ryanodine receptor expression correlates with tumor grade in breast cancer. PubMed: Plastic components affect the activation of the aryl hydrocarbon and the androgen receptor. PubMed: Identification and biochemical characterization of a novel ryanodine receptor gene mutation associated with malignant hyperthermia. PubMed: Rem inhibits skeletal muscle EC coupling by reducing the number of functional L-type Ca2+ channels. PubMed: Sarcoplasmic reticulum Ca2+ release declines in muscle fibers from aging mice. PubMed: Dynamics of intracellular oxygen in PC12 Cells upon stimulation of neurotransmission. PubMed: Quantitative determination of chlorophenols in leather by pressurized liquid extraction and liquid chromatography with diode-array detection. PubMed: A catalytically active molecularly imprinted polymer that mimics peroxidase based on hemin: application to the determination of p-aminophenol. PubMed: 4-Chloro-m-cresol, an activator of ryanodine receptors, inhibits voltage-gated K(+) channels at the rat calyx of Held. PubMed: Identification of functional type 1 ryanodine receptors in human dendritic cells. PubMed: Functional ryanodine receptors are expressed by human microglia and THP-1 cells: Their possible involvement in modulation of neurotoxicity. PubMed: Increased Ca2+ storage capacity of the skeletal muscle sarcoplasmic reticulum of transgenic mice over-expressing membrane bound calcium binding protein junctate. PubMed: Evaluation of estrogenic activity of organic biocides using ER-binding and YES assay. PubMed: Na+ entry via glutamate transporter activates the reverse Na+/Ca2+ exchange and triggers Ca(i)2+-induced Ca2+ release in rat cerebellar Type-1 astrocytes. PubMed: The Sonogel-Carbon materials as basis for development of enzyme biosensors for phenols and polyphenols monitoring: a detailed comparative study of three immobilization matrixes. PubMed: [Effects of agonists and antagonists of rhyanodine receptors on potassium contractures in twitch and tonic frog skeletal muscle fibers]. PubMed: Pharmacologic and functional characterization of malignant hyperthermia in the R163C RyR1 knock-in mouse. PubMed: Alterations in calcium homeostasis reduce membrane excitability in amphibian skeletal muscle. PubMed: Amino acid residues Gln4020 and Lys4021 of the ryanodine receptor type 1 are required for activation by 4-chloro-m-cresol. PubMed: Characterization of ryanodine receptor-mediated calcium release in human B cells: relevance to diagnostic testing for malignant hyperthermia. PubMed: Structural determinants of 4-chloro-m-cresol required for activation of ryanodine receptor type 1. PubMed: Knocking down type 2 but not type 1 calsequestrin reduces calcium sequestration and release in C2C12 skeletal muscle myotubes. PubMed: Development of a high analytical performance-tyrosinase biosensor based on a composite graphite-Teflon electrode modified with gold nanoparticles. PubMed: Can 4-chloro-m-cresol be substituted for caffeine as an activator of calcium oscillation in bullfrog sympathetic ganglion cells? PubMed: Oxidation of myosin heavy chain and reduction in force production in hyperthyroid rat soleus. PubMed: Effects of caffeine, halothane, and 4-chloro-m-cresol on skeletal muscle lactate and pyruvate in malignant hyperthermia-susceptible and normal swine as assessed by microdialysis. PubMed: Functional properties of ryanodine receptors carrying three amino acid substitutions identified in patients affected by multi-minicore disease and central core disease, expressed in immortalized lymphocytes. PubMed: Blockade of intracellular calcium release induces an antidepressant-like effect in the mouse forced swimming test. PubMed: Non-specific effects of 4-chloro-m-cresol may cause calcium flux and respiratory burst in human neutrophils. PubMed: Ryanodine receptors are involved in muscarinic antinociception in mice. PubMed: Simultaneous determination of phenolic compounds by means of an automated voltammetric "electronic tongue". PubMed: Membrane-assisted solvent extraction of seven phenols combined with large volume injection-gas chromatography-mass spectrometric detection. PubMed: Caffeine induced Ca2+ release and capacitative Ca2+ entry in human embryonic kidney (HEK293) cells. PubMed: Enhanced response to caffeine and 4-chloro-m-cresol in malignant hyperthermia-susceptible muscle is related in part to chronically elevated resting [Ca2+]i. PubMed: Role of intracellular calcium in acute thermal pain perception. PubMed: Mutational analysis of putative calcium binding motifs within the skeletal ryanodine receptor isoform, RyR1. PubMed: Effect of ryanodine receptor mutations on interleukin-6 release and intracellular calcium homeostasis in human myotubes from malignant hyperthermia-susceptible individuals and patients affected by central core disease. PubMed: 4-chloro-m-cresol cannot detect malignant hyperthermia equivocal cells in an alternative minimally invasive diagnostic test of malignant hyperthermia susceptibility. PubMed: Human muscle sarcoplasmic reticulum function during submaximal exercise in normoxia and hypoxia. PubMed: Functional characterization of malignant hyperthermia-associated RyR1 mutations in exon 44, using the human myotube model. PubMed: Prolonged exercise to fatigue in humans impairs skeletal muscle Na+-K+-ATPase activity, sarcoplasmic reticulum Ca2+ release, and Ca2+ uptake. PubMed: Differential regulation of calcium homeostasis in adenocarcinoma cell line A549 and its Taxol-resistant subclone. PubMed: Optimization by experimental design and artificial neural networks of the ion-interaction reversed-phase liquid chromatographic separation of twenty cosmetic preservatives. PubMed: Influence of intracellular Ca2+ release modulating drugs on bupivacaine infiltration anesthesia in mice. PubMed: Comparison of gas chromatography-mass spectrometry and capillary electrophoresis in analysis of phenolic compounds extracted from solid matrices with pressurized hot water. PubMed: The calmodulin binding region of the skeletal ryanodine receptor acts as a self-modulatory domain. PubMed: Calcium release from sarcoplasmic reticulum is facilitated in human myotubes derived from carriers of the ryanodine receptor type 1 mutations Ile2182Phe and Gly2375Ala. PubMed: Supramolecular structures of 2-chloro-5-methylphenol and 4-chloro-3-methylphenol (chlorocresol). PubMed: Ryanodine receptor mutations associated with stress-induced ventricular tachycardia mediate increased calcium release in stimulated cardiomyocytes. PubMed: Multicentre evaluation of in vitro contracture testing with bolus administration of 4-chloro-m-cresol for diagnosis of malignant hyperthermia susceptibility. PubMed: Critical amino acid residues determine the binding affinity and the Ca2+ release efficacy of maurocalcine in skeletal muscle cells. PubMed: Ca(2+)-induced Ca(2+) release in the pancreatic beta-cell: direct evidence of endoplasmic reticulum Ca(2+) release. PubMed: The Ile2453Thr mutation in the ryanodine receptor gene 1 is associated with facilitated calcium release from sarcoplasmic reticulum by 4-chloro-m-cresol in human myotubes. PubMed: Identification of a key determinant of ryanodine receptor type 1 required for activation by 4-chloro-m-cresol. PubMed: Myoplasmic calcium regulation in myotubes from horses with recurrent exertional rhabdomyolysis. PubMed: Calcium homeostasis and glucose uptake of murine myotubes exposed to insulin, caffeine and 4-chloro-m-cresol. PubMed: In situ modulation of the human cardiac ryanodine receptor (hRyR2) by FKBP12.6. PubMed: Detection of proton release from cultured human myotubes to identify malignant hyperthermia susceptibility. PubMed: Patients with malignant hyperthermia demonstrate an altered calcium control mechanism in B lymphocytes. PubMed: H2O2 activates ryanodine receptor but has little effect on recovery of releasable Ca2+ content after fatigue. PubMed: Increased sensitivity to 4-chloro-m-cresol and caffeine in primary myotubes from malignant hyperthermia susceptible individuals carrying the ryanodine receptor 1 Thr2206Met (C6617T) mutation. PubMed: Calmodulin binding to the 3614-3643 region of RyR1 is not essential for excitation-contraction coupling in skeletal myotubes. PubMed: Comparison of two screening level risk assessment approaches for six disinfectants and pharmaceuticals. PubMed: Functional properties of EGFP-tagged skeletal muscle calcium-release channel (ryanodine receptor) expressed in COS-7 cells: sensitivity to caffeine and 4-chloro-m-cresol. PubMed: Silver ions induce Ca2+ release from the SR in vitro by acting on the Ca2+ release channel and the Ca2+ pump. PubMed: Identification of functional type 1 ryanodine receptors in mouse dendritic cells. PubMed: Sarcoplasmic reticulum Ca(2+) content affects 4-CmC and caffeine contractures of rat skinned skeletal muscle fibers. PubMed: Requirement of functional ryanodine receptor type 3 for astrocyte migration. PubMed: Phenolic xenoestrogens in surface water, sediments, and sewage sludge from Baden-Württemberg, south-west Germany. PubMed: Mutations to Gly2370, Gly2373 or Gly2375 in malignant hyperthermia domain 2 decrease caffeine and cresol sensitivity of the rabbit skeletal-muscle Ca2+-release channel (ryanodine receptor isoform 1). PubMed: Expression of the ryanodine receptor isoforms in immune cells. PubMed: B-lymphocytes from malignant hyperthermia-susceptible patients have an increased sensitivity to skeletal muscle ryanodine receptor activators. PubMed: Oxidation of 4-chloro-3-methylphenol in pressurized hot water/supercritical water with potassium persulfate as oxidant. PubMed: Trace level determination of phenols as pentafluorobenzyl derivatives by gas chromatography-negative-ion chemical ionization mass spectrometry. PubMed: Selective trace level analysis of phenolic compounds in water by flow injection analysis--membrane introduction mass spectrometry. PubMed: Hyperbolic Spirals as Surface Structures in Thin Layers. PubMed: Fiberoptic biosensors based on chemiluminescent reactions. PubMed: Multiple effects of caffeine on Ca2+ release and influx in human B lymphocytes. PubMed: Divergent functional properties of ryanodine receptor types 1 and 3 expressed in a myogenic cell line. PubMed: Differential effects of 4-chloro-m-cresol and caffeine on skinned fibers from rat fast and slow skeletal muscles. PubMed: Evidence of functional ryanodine receptor involved in apoptosis of prostate cancer (LNCaP) cells. PubMed: Polyamine triggering of exocytosis in Paramecium involves an extracellular Ca(2+)/(polyvalent cation)-sensing receptor, subplasmalemmal Ca-store mobilization and store-operated Ca(2+)-influx via unspecific cation channels. PubMed: Input/output balance of estrogenic active compounds in a major municipal sewage plant in Germany. PubMed: Development and validation of a GC/MS method for determination of phenolic xenoestrogens in aquatic samples. PubMed: Mobilization of Ca2+ stores in individual pancreatic beta-cells permeabilized or not with digitonin or alpha-toxin. PubMed: The impact of 4-chloro-m-cresol in heparin formulas on malignant hyperthermia: in vitro and in vivo. PubMed: A multicenter study of 4-chloro-m-cresol for diagnosing malignant hyperthermia susceptibility. PubMed: Generation of novel bacterial regulatory proteins that detect priority pollutant phenols. PubMed: Voltage-dependent block of normal and mutant muscle sodium channels by 4-Chloro-m-Cresol. PubMed: The role of calcium stores in fatigue of isolated single muscle fibres from the cane toad. PubMed: Sarcoplasmic reticulum Ca(2+) release by 4-chloro-m-cresol (4-CmC) in intact and chemically skinned ferret cardiac ventricular fibers. PubMed: Intracellular Ca2+ transients in mouse soleus muscle after hindlimb unloading and reloading. PubMed: Measurement of sarcoplasmic reticulum Ca2+ content in intact amphibian skeletal muscle fibres with 4-chloro-m-cresol. PubMed: A transient and a persistent calcium release are induced by chlorocresol in cultivated mouse myotubes. PubMed: 4-chloro-m-cresol is a trigger of malignant hyperthermia in susceptible swine. PubMed: 4-chloro-m-cresol triggers malignant hyperthermia in susceptible swine at doses greatly exceeding those found in drug preparations. PubMed: Solid-phase microextraction of the antifouling Irgarol 1051 and the fungicides dichlofluanid and 4-chloro-3-methylphenol in water samples. PubMed: Secretagogues modulate the calcium concentration in the endoplasmic reticulum of insulin-secreting cells. Studies in aequorin-expressing intact and permeabilized ins-1 cells. PubMed: Skeletal muscle type ryanodine receptor is involved in calcium signaling in human B lymphocytes. PubMed: Modification of excitation-contraction coupling by 4-chloro-m-cresol in voltage-clamped cut muscle fibres of the frog (R. pipiens). PubMed: Validation and application of a rapid in vitro assay for assessing the estrogenic potency of halogenated phenolic chemicals. PubMed: Functional consequences of mutations of conserved, polar amino acids in transmembrane sequences of the Ca2+ release channel (ryanodine receptor) of rabbit skeletal muscle sarcoplasmic reticulum. PubMed: Effects of ryanodine receptor agonist 4-chloro-m-cresol on myoplasmic free Ca2+ concentration and force of contraction in mouse skeletal muscle. PubMed: Effects of varied fatigue protocols on sarcoplasmic reticulum calcium uptake and release rates. PubMed: Functional aspects of skeletal muscle contractile apparatus and sarcoplasmic reticulum after fatigue. PubMed: E-C coupling failure in mouse EDL muscle after in vivo eccentric contractions. PubMed: Gas-phase postderivatization following solid-phase microextraction for determining acidic herbicides in water. PubMed: [4-chloro-m-cresol-induced contractures of skeletal muscle specimen from patients at risk for malignant hyperthermia]. PubMed: 4-Chloro-m-cresol test--a possible supplementary test for diagnosis of malignant hyperthermia susceptibility. PubMed: Classification of malignant hyperthermia-equivocal patients by 4-chloro-M-cresol. PubMed: Functional characterization of a distinct ryanodine receptor mutation in human malignant hyperthermia-susceptible muscle. PubMed: 4-Chloro-m-cresol: a specific tool to distinguish between malignant hyperthermia-susceptible and normal muscle. PubMed: Oscillations of cytosolic free calcium in bombesin-stimulated HIT-T15 cells. PubMed: 4-Chloro-m-cresol, a potent and specific activator of the skeletal muscle ryanodine receptor. PubMed: Alteration of intracellular Ca2+ transients in COS-7 cells transfected with the cDNA encoding skeletal-muscle ryanodine receptor carrying a mutation associated with malignant hyperthermia. PubMed: Development of an amperometric biosensor for the determination of phenolic compounds in reversed micelles. PubMed: Chlorocresol: an activator of ryanodine receptor-mediated Ca2+ release. PubMed: Degradation of phenol and phenolic compounds by Pseudomonas putida EKII. PubMed: The synergistic effect of chlorinated chemicals (trichlorosalicylanilid, 4-chloro-m-cresol, trichlorophenoxyacetic acid, trichloroethanol, trichloromethiazide, trichlorofon and trichloroacetaldehyde) and low concentrations of griseofulvin on porphyrin metabolism. PubMed: Use of polymeric sorbents for the off-line preconcentration of priority pollutant phenols from water for high-performance liquid chromatographic analysis. PubMed: The effect of chlorinated chemicals on porphyrin metabolism--the synergistic effect with chlorinated chemicals and low concentrations of griseofulvin. PubMed: Irritant dermatitis from tri-butyl tin oxide and contact allergy from chlorocresol. PubMed: 4-Chloro-3-methylphenol: Salmonella/mammalian-microsome mutagenicity test and subacute toxicity test in rats. PubMed: Effects of heparin on prostacyclin binding and platelet adenylate cyclase activity stimulated by iloprost and forskolin. PubMed: [On the bacteriostatic and antifungal activity of some benzyl derivatives of 4-chloro-m-cresol].