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Home > Encyclopedia > 4-Methylquinoline

4-Methylquinoline

4-Methylquinoline structure

4-Methylquinoline 

structure
  • CAS No:

    491-35-0

  • Formula:

    C10H9N

  • Chemical Name:

    4-Methylquinoline

  • Synonyms:

    Quinoline,4-methyl-;Lepidine;4-Methylquinoline;Cincholepidine;4-Lepidine;Lepidin;γ-Methylquinoline;NSC 3412

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

clear slightly yellow to brown liquid


4-methylquinoline is a methylquinoline carrying a methyl substituent at position 4. It has a role as a mutagen.

4-Methylquinoline Basic Attributes

143.19

143.19

110926

207-734-2

116169T3O8

3412

DTXSID7047067

Colorless, oily liquid

29334900

Characteristics

12.9

2.61

Liquid

1.0826 g/cm3 @ Temp: 20 °C

9.5 °C

261-263 °C

>230 °F

n20/D 1.620(lit.)

H2O: Slightly soluble

Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

6.4X10-3 mm Hg @ 20 deg C /Extrapolated/

Thermal decomposition of toxic nitrogen oxide gas

Quinoline odor

Henry's Law constant = 7.60X10-7 atm-cu m/mole @ 25 °C /Estimated/

pKa = 5.67 at 20 °C (conjugate acid)

Turns reddish-brown in light|Solidifies at about 0 °C|Hydroxyl radical reaction rate constant = 3.04X10-11 cu m/molecule-sec @ 25 °C /Estimated/

Safety Information

NONH for all modes of transport

3

36/37/38-68-40

26-36-45-36/37/39-22

OH0316000

Xi,Xn

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Protect from light.

P261-P305 + P351 + P338

H315-H319-H335

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

4-Methylquinoline is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P312, P322, P330, P337+P313, P363, and P501

SEDIMENT: 4-Methylquinoline was found in Eagle harbor sediment (Puget Sound, WA) contaminated with creosote at concns <0.19 ug/g(1).

Toxicity

Quinoline and all 7 positional isomers of methylquinoline were assayed for tumor-initiating activity on the skin of SENCAR female mice with promotion by tetradecanoyl phorbol acetate. ... Quinoline induced tumors in 53% of the mice (0.73 tumors per animal). While 2-, 3-, 5- and 7-methylquinoline did not exhibit significant tumorigenic activity in this assay, 4-methylquinoline induced tumors in 45% of the mice (0.90 tumors per animal). 8-Methylquinoline induced tumors in 45% of the mice (0.66 tumors per animal).

4-Methylquinoline's production and use in organic preparations(1), as a medicine(1), and as a food additive(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 630(SRC), determined from a log Kow of 2.61(2) and a regression-derived equation(3), indicates that 4-methylquinoline is expected to have low mobility in soil(SRC). The pKa of 4-methylquinoline is 5.67(4), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(5). Volatilization of 4-methylquinoline from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.6X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(6). 4-Methylquinoline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.4X10-3 mm Hg(7). Based on ananerobic studies in water, 4-methylquinoline is expected to degrade in soil under anaerobic conditions(SRC). Slurries from methanogenic freshwater sediment transformed 4-methylquinoline after anaerobic incubation for 106 days at 25 °C(8).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 630(SRC), determined from a log Kow of 2.61(2) and a regression-derived equation(3), indicates that 4-methylquinoline is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 7.6X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 18 and 200 days, respectively(SRC). The pKa of 4-methylquinoline is 5.67(5), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(6). According to a classification scheme(7), an estimated BCF of 20(SRC), from its log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Slurries from methanogenic freshwater sediment transformed 4-methylquiloline after anaerobic incubation for 106 days at 25 °C(9). Using groundwater medium from a creosote contaminated medium (i.e., from American Creosote Works site in Pensacola, FL), 4-methylquinoline degraded from an initial concn of 0.7 ug/ml to 0.2 ug/ml in 14 days(10). The major product of anaerobic degradation of 4-methylquinoline is 4-methyl-2(1H)-quinolinone while the minor products are 1,4-dimethyl-2(1H)-quinolinone and 2-methoxy-4-methyl-quinoline(11).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-methylquinoline, which has a vapor pressure of 6.4X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the particulate phase in the ambient atmosphere(SRC). Vapor-phase 4-methylquinoline is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 13 hrs(SRC), calculated from its rate constant of 3.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 4-Methylquinoline is expected to undergo direct photolysis based on adsorption of light at wavelengths >290 nm(4).

The rate constant for the vapor-phase reaction of 4-methylquinoline with photochemically-produced hydroxyl radicals has been estimated as 3.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 13 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4-Methylquinoline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). 4-Methylquinoline is expected to undergo direct photolysis based on adsorption of light at wavelengths >290 nm(3).

An estimated BCF of 20 was calculated for 4-methylquinoline(SRC), using a log Kow of 2.61(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of 4-methylquinoline is estimated as 630(SRC), using a log Kow of 2.61(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 4-methylquinoline is expected to have low mobility in soil(SRC). The pKa of 4-methylquinoline is 5.67(4), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(5).

The Henry's Law constant for 4-methylquinoline is estimated as 7.6X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4-methylquinoline is expected to be essentially nonvolatile from water surfaces(2). 4-Methylquinoline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.4X10-3 mm Hg(3).

GROUNDWATER: In 1983, 4-methylquinoline was detected in 2 groundwater wells at an abandoned creosote works located in Pensicola, FL(1). Concns of 4-methylquinoline were 0.21 mg/liter and ranged from 0.00 to 0.02 mg/liter in these groundwater wells(1). In June 1986, the concn of 4-methylquinoline in groundwater was 730 ug/liter at a creosote contaminated site in Pensacola, FL(2). In October, 1986, the concn of 4-methylquinoline in groundwater was <18 ng/liter at a coal tar contaminated site in St. Louis, Park, MN(2).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,557 workers (276 of these are female) are potentially exposed to 4-methylquinoline in the US(1). Occupational exposure to 4-methylquinoline may occur through dermal contact with this compound at workplaces where 4-methylquinoline is produced or used(SRC). Monitoring data indicate that the general population may be exposed to 4-methylquinoline with the use of this compound for medicinal purposes and as a food additive(SRC).

Drug Information

Some 4-methylquinoline metabolites have been identified from in vitro studies. 4-methylquinoline subjected to metabolism for 60 minute by S-9 microsomal fraction prepared from 3-methylchloanthrene-induced rat liver... /identified/ the primary metabolites ... as 4-hydroxymethylquinoline (38.7%), 3-hydroxy-4-hydroxy-methylquinoline (8.0%), 4methylquinoline -N-oxide (3.6%), and 3-hydroxy-4-methylquinoline (1.6%).|The major metabolite of 4-MeQ was 4-hydroxymethylquinoline, which was not mutagenic under the assay condition employed.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

4-methylquinoline

4-Methylquinoline Use and Manufacturing

Methods of Manufacturing

4-Methylquinoline can be recovered from the highest-boiling fraction of the coal-tar quinoline bases via its o-cresol addition compound. It can be synthesized by condensation of aniline and methyl vinyl ketone.

Uses

Used as an intermediate for dyes, medicine, and photosensitive materials.

Quinoline, 4-methyl-: ACTIVE

Computed Properties

Molecular Weight:143.18
XLogP3:2.6
Hydrogen Bond Acceptor Count:1
Exact Mass:143.073499291
Monoisotopic Mass:143.073499291
Topological Polar Surface Area:12.9
Heavy Atom Count:11
Complexity:133
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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