2-(1-Iodoethyl)-1,3-dioxolane-4-methanol
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2-(1-Iodoethyl)-1,3-dioxolane-4-methanol
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CAS No:
5634-39-9
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Formula:
C6H11IO3
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Chemical Name:
2-(1-Iodoethyl)-1,3-dioxolane-4-methanol
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Synonyms:
1,3-Dioxolane-4-methanol,2-(1-iodoethyl)-;2-(1-Iodoethyl)-1,3-dioxolane-4-methanol;Organidin
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CAS No:
Description
PHYSICAL DESCRIPTION: Viscous pale yellow or yellow liquid. (NTP, 1992)
Iodinated glycerol appears as viscous pale yellow or yellow liquid. (NTP, 1992)
Iodinated glycerol appears as viscous pale yellow or yellow liquid. (NTP, 1992)|Iodinated glycerol is a dioxolane.
2-(1-Iodoethyl)-1,3-dioxolane-4-methanol Basic Attributes
258.05400
258.05
227-079-6
34ON63CCO3
DTXSID4020741
PALE YELLOW LIQ
Characteristics
38.69000
0.54370
Iodinated glycerol appears as viscous pale yellow or yellow liquid. (NTP, 1992)
1.797 g/cm3
<25 °C
294.9ºC at 760 mmHg
132.1ºC
1.545
SOL IN ETHER, CHLOROFORM, ISOBUTYL ALC, METHYL ACETATE, ETHYL ACETATE, METHYL FORMATE, TETRAHYDROFURAN
4.25 mm Hg at 77° F (NTP, 1992)
PUNGENT, BITTER AFTERTASTE
Water soluble.
Alcohols and Polyols
A halogenated alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.
Safety Information
DHHS/NTP; Toxicology & Carcinogenesis Studies of Iodinated Glycerol in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 340 (1990) NIH Publication No. 90-2596
This chemical is probably combustible. (NTP, 1992)
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in a refrigerator. (NTP, 1992)
MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)
Toxicity
Toxicology and carcinogenesis studies of iodinated glycerol (Orgarlidin, a complex mixture prepared by the reaction of iodine with glycerol and found to contain 33% 3-iodo-1,2-propanediol as the major component) were conducted because of human exposure to iodinated glycerol as an expectorant and its possible relationship to the formation of alkyl iodides, e.g., methyl iodide, a suspected animal carcinogen. These studies were conducted by giving iodinated glycerol in water by gavage (5 days per week) to groups of F344/N rats and B6C3F1 mice for ... 2 years. ... Two yr studies were conducted by administering 0, 125, or 250 mg/kg iodinated glycerol in deionized water by gavage, 5 days/wk for 103 wk, to groups of 50 male F344/N rats and 50 male B6C3F1 mice. Groups of 50 female F344/N rats and 50 female B6C3F1 mice were admin iodinated glycerol on the same schedule at lower doses of 0, 62 or 125 mg/kg because of the incr severity of kidney and stomach lesions in the 13 wk studies. Conclusions: Under the conditions of these 2 yr gavage studies, there was some evidence of carcinogenic activity for male F344/N rats admin iodinated glycerol, as indicated by increased incidences of mononuclear cell leukemia and follicular cell carcinomas of the thyroid gland. Adenomas of the nasal cavity in two high dose male rats may have been related to the administration of iodinated glycerol. There was no evidence of carcinogenic activity for female F344/N rats administered 62 or 125 mg/kg iodinated glycerol by gavage for 103 wk. There was no evidence of carcinogenic activity for male B6C3F1 mice administered 125 or 250 mg/kg iodinated glycerol by gavage for 103 wk. There was some evidence of carcinogenic activity for female B6C3F1 mice admin iodinated glycerol, as indicated by incr incidences of adenomas of the anterior pituitary gland and neoplasms of the harderian gland. Squamous cell papillomas of the forestomach may have been related to the admin of iodinated glycerol.
Drug Information
Expectorants|...IT IS CLAIMED TO HAVE EXPECTORANT ACTIONS OF IODINE & GLYCERIN & DOES NOT CAUSE GASTRIC IRRITATION OR RELEASE INORGANIC IODINE BEFORE ABSORPTION.
EFFICACY OF IODINATED GLYCERIN IS QUESTIONABLE... SENSITIVITY REACTIONS OCCUR OCCASIONALLY. THEREFORE, IODINATED GLYCERIN IS CONTRAINDICATED IN PT WHO ARE SENSITIVE TO IODINE.
SYMPTOMS: Symptoms of exposure to this compound include hypersensitivity, rash, flare-up of adolescent acne, dermatitis, gastrointestinal irritation, thyroid gland enlargement and acute parotitis. Compounds of this type have caused mental depression, insomnia, sexual impotence, hyperthyroidism, goiter, hypersensitivity characterized by severe coryza, headache, lacrimation, weakness, laryngitis, bronchitis, allergic reactions, irritation of the mucous membranes and death due to circulatory failure, edema of the glottis resulting in asphyxia, aspiration pneumonia or pulmonary edema. Skin reactions (iododerma) may vary from mild erythema and acneform eruptions to urticaria. Suppurative or hemorrhagic rashes may also result. Other symptoms may include myxedema, nervousness, iodism, pain and swelling in the salivary glands, conjunctivitis, fever, exacerbation of acne, esophageal stricture, anuria, disagreeable metallic taste, vomiting, abdominal pain and diarrhea. If the stomach contains starch the vomitus is colored blue. Exposure may also lead to thirst, shock, nausea, delirium, stupor, temporary enlargement of lymph glands respiratory distress, stomatitis, rhinorrhea, anorexia, weight loss, sleeplessness, laryngeal edema, serum sickness with lymph node enlargement, joint pain and swelling, collapse, coma and death from uremia. ACUTE/CHRONIC HAZARDS: This compound may cause allergic skin reactions. Compounds of this type can be irritating to the mucous membranes. (NTP, 1992)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)
glycerol, iodinated
2-(1-Iodoethyl)-1,3-dioxolane-4-methanol Use and Manufacturing
REACTION OF IODINE AND GLYCEROL|MANCHEY ET AL, US PATENT 2,872,378 (1959 TO DENVER CHEM MFR).
Expectorant.
(1977) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS
ORGANIDIN... ORAL: ELIXIR 1.2%; SOLN 5%; TABLETS 30 MG.
ISOMERIC MIXT OF 67-75% OF 2-(1-IODOETHYL)-1,3-DIOXOLANE-4-METHANOL OR 2,3-(2-IODOPROPYLIDENEDIOXY)PROPANOL & 33-25% OF 2-(2-IODOETHYL)-1,3-DIOXOLANE-4-METHANOL OR 2,3-(3-IODOPROPYLIDENEDIOXY)PROPANOL.
Computed Properties
Molecular Weight:258.05
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:257.97529
Monoisotopic Mass:257.97529
Topological Polar Surface Area:38.7
Heavy Atom Count:10
Complexity:109
Undefined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
2-(1-Iodoethyl)-1,3-dioxolane-4-methanol
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