3-(4-chlorophenoxy)propane-1,2-diol

• ChemBase ID: 734
• Molecular Formular: C9H11ClO3
• Molecular Mass: 202.63484
• Monoisotopic Mass: 202.03967189
• SMILES: Clc1ccc(OCC(O)CO)cc1
• Canonical SMILES: OCC(COc1ccc(cc1)Cl)O
• InChI: InChI=1S/C9H11ClO3/c10-7-1-3-9(4-2-7)13-6-8(12)5-11/h1-4,8,11-12H,5-6H2
• InChIKey: MXOAEAUPQDYUQM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-chlorophenoxy)propane-1,2-diol
• IUPAC Traditional name: chlorphenesin; C9H11ClO3
• Brand Name: Adermykon; Demykon; Gechophen; Gecophen; Maolate; Mycil
• Synonyms: 3-(4-chlorophenoxy)propane-1,2-diol; (±)-p-Chlorphenesin; 3-(4-Chlorophenoxy)-1,2-propanediol; 3-(p-Chlorophenoxy)propane-1,2-diol; Adermykon; Chlorphenesin; Demykon; Elestab CPN; Gecophen; Glycerol α-p-chlorophenyl ether; Mycil; NSC 6401; p-Chlorophenyl-α-glyceryl ether; p-Chlorphenesin; 3-(4-Chlorophenoxy)-1,2-propanediol; Chlorphenesine [INN-French]; Chlorophenesin; alpha-Glyceryl ether; Chlorphenesinum [INN-Latin]; Clorfenesina [INN-Spanish]; p-Chlorophenyl; p-Chlorophenyl glyceryl ether; Chlorphenesin; 3-(4-氯苯氧基)-1,2-丙二醇

Database IDs

• CAS Number: 104-29-0
• EC Number: 203-192-6
• MDL Number: MFCD00021990
• PubChem SID: 46504714; 160964197
• PubChem CID: 7697

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.624308
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.0991822
• LogD (pH = 7.4): 1.099182
• Log P: 1.0991822
• Molar Refractivity: 49.5808 cm^3
• Polarizability: 19.680779 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.46
• LOG S: -1.29
• Solubility (Water): 1.04e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1E+004 mg/L; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 78-82°C; 79-81°C
• Hydrophobicity(logP): 1.2; 1.216

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• RTECS: TY4260000
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 95%; 99%

DETAILS

DrugBank - DB00856

• Drug Groups: approved
• Description: A centrally acting muscle relaxant. Its mode of action is unknown. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1203)
• Indication: Used, along with rest and physical therapy, to treat injuries and other painful muscular conditions. Investigated for use in trigeminal neuralgia (tic douloureux), a neuropathic disorder characterized by severe facial pain. Was investigated as a modulator of histamine release.
• Pharmacology: Chlorphenesin is a muscle relaxant. It blocks nerve impulses (or pain sensations) that are sent to the brain.
• Toxicity: Symptoms of a chlorphenesin overdose include drowsiness and nausea.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. 85% of a dose excreted within 24 hours as the glucuronide metabolite.
• Absorption: Rapid and complete.
• Half Life: 2.3-5 hours
• References: Malley A, Baecher L: Inhibition of histamine and SRS-A from monkey lung tissue by chlorophenesin. J Immunol. 1971 Aug;107(2):586-8. [Pubmed] ; Kurachi M, Aihara H: Effect of a muscle relaxant, chlorphenesin carbamate, on the spinal neurons of rats. Jpn J Pharmacol. 1984 Sep;36(1):7-13. [Pubmed] ; Dalessio DJ: Medical treatment of the major neuralgias. Semin Neurol. 1988 Dec;8(4):286-90. [Pubmed]
• External Links: Drugs.com

Toronto Research Chemicals - C424250

Chlorphenesin is an antigen-associated immunosuppressant that inhibits IgE-mediated histamine release. Chlorphenesin is also used as an antimycotic agent.

REFERENCES

• Malley A, Baecher L: Inhibition of histamine and SRS-A from monkey lung tissue by chlorophenesin. J Immunol. 1971 Aug;107(2):586-8. Pubmed
• Kurachi M, Aihara H: Effect of a muscle relaxant, chlorphenesin carbamate, on the spinal neurons of rats. Jpn J Pharmacol. 1984 Sep;36(1):7-13. Pubmed
• Dalessio DJ: Medical treatment of the major neuralgias. Semin Neurol. 1988 Dec;8(4):286-90. Pubmed
• Whang, H.Y. et al.: Infect. Immun., 2, 60 (1970)
• Lichtenstein, L.M. et al.: J. Immunol., 103, 866 (1970)
• Thoma, K. et al.: Pharmazie, 52, 362 (1970)