Gamma-Nonalactone

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that dihydro-5-pentyl-2(3H)-furanone is expected to have high mobility in soil(SRC). Volatilization of dihydro-5-pentyl-2(3H)-furanone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.7X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Dihydro-5-pentyl-2(3H)-furanone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.2X10-2 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Using a Closed Bottle test, dihydro-5-pentyl-2(3H)-furanone achieved 71% biodegradation in activated sewage sludge after 28 days(4), suggesting that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that dihydro-5-pentyl-2(3H)-furanone is not 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 1.7X10-4 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 10 hours and 7 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 11(SRC), from an estimated log Kow of 2.08(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). By analogy to gamma-butyolactone, which exhibits a hydrolysis half-life of approximately 28 days at pH7, dihydro-5-pentyl-2(3H)-furanone is expected to hydrolyze under environmental conditions (pH 5 to 9). Using a Closed Bottle test(6), dihydro-5-pentyl-2(3H)-furanone achieved 71% biodegradation in activated sewage sludge after 28 days(6), suggesting that biodegradation is an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dihydro-5-pentyl-2(3H)-furanone, which has an estimated vapor pressure of 1.2X10-2 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dihydro-5-pentyl-2(3H)-furanone 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 40 hours(SRC), calculated from its rate constant of 9.7X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Dihydro-5-pentyl-2(3H)-furanone contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Dihydro-5-pentyl-2(3H)-furanone has been detected in the volatile constituents of nectarines (1,2), concentrations were less than 10 ppb in samples obtained from orchards of the Horticultural Crops Research Laboratory of the US Agricultural Department, Fresno, CA (Sunfire, Flavortop, P 62-27, P 89-56)(1). Dihydro-5-pentyl-2(3H)-furanone was detected at a concentration of 5 ug/kg in fresh apricot fruit tissue; it was not detected in 2 other apricot varieties nor in 2 plum varieties(3). Dihydro-5-pentyl-2(3H)-furanone has been identified but not quantified as a volatile component of roasted filbert tree nuts (Corylus avellana)(4). Dihydro-5-pentyl-2(3H)-furanone was detected in white, rose, and red wines (72 total samples) at mean concentrations of 14.77, 19.98, and 42.09 ug/L(5). Dihydro-5-pentyl-2(3H)-furanone is reported in peaches, apricots, roasted barely, rum, tomato, currants, guave, raisin, papaya, peach, pineapple, blackberry, strawberry jam, asparagus, wheat and crisp bread, chicken beef, lamb and pork fat, cooked beef and pork, beer, cognac, whiskies, sherry, grape wines, cocoa, green tea, pecan, oats, soybean, avocado, passion fruit, plumcot, beans, mushroom, starfruit, fenugreek, mango, tamarind, rice, prickly pear, buckwheat, licorice, malt, wort, cherimoya, Bourbon vanilla, mate, and sweet grass oil(6).

IDENTIFICATION AND USE: Dihydro-5-pentyl-2(3H)-furanone is an essential oil used in perfumery and flavors. It is not registered for current pesticide use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. HUMAN EXPOSURE AND TOXICITY: A maximization test was carried out on 25 volunteers. Dihydro-5-pentyl-2(3H)-furanone was tested at a concentration of 10% in petrolatum and produced no sensitization reactions. Tested at 10% in petrolatum, Dihydro-5-pentyl-2(3H)-furanone produced no irritation after a 48 hr closed-patch test on human subjects. ANIMAL STUDIES: A 90-day feeding study on 15 male and 15 female rats fed 0 or 67.5 mg/kg Dihydro-5-pentyl-2(3H)-furanone body wt/day showed no adverse effect. 0.1-0.5% Dihydro-5-pentyl-2(3H)-furanone fed to groups of 20 male and female rats in diet for 2 yr produced no effects. In a 2-wk study, 61.4 mg/kg Dihydro-5-pentyl-2(3H)-furanone fed to rats in the diet produced no effects. Gamma-nonalactone applied full strength to intact or abraded rabbit skin for 24 hr under occlusion was slightly irritating.

Dihydro-5-pentyl-2(3H)-furanone has been detected in raw earth almond (Cyperus esculentus), a weed-like plant native to Africa and Southern Europe, and roasted earth almond after 10, 20, 30, 40, 50, and 60 minute roasting times, decreasing in concentration from 0.4% peak area at 10 minutes to <0.01% at 60 minutes(1).

EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; Click on the "Chemical Explorer" button on the tool bar to see the data./[USEPA; ICSS Dashboard Application; Available from, as of April 22, 2015: http://actor.epa.gov/dashboard/]

Using a structure estimation method based on molecular connectivity indices(1), the Koc of dihydro-5-pentyl-2(3H)-furanone can be estimated to be 120(SRC). According to a classification scheme(2), this estimated Koc value suggests that dihydro-5-pentyl-2(3H)-furanone is expected to have high mobility in soil.

Dihydro-5-pentyl-2(3H)-furanone is reported in peaches, apricots, tomato, currants, guave, raisin, papaya, peach, pineapple, blackberry, asparagus, cocoa, pecan, oats, soybean, avocado, passion fruit, plum, plumcot, beans, mushroom, starfruit, fenugreek, mango, tamarind, rice, prickly pear, buckwheat, licorice, malt, wort, cherimoya, nectarine, mate, and sweet grass oil(1).

/HUMAN EXPOSURE STUDIES/ A maximization test was carried out on 25 volunteers. ... /Gamma-nonalactone/ was tested at a concentration of 10% in petrolatum and produced no sensitization reactions.

/HUMAN EXPOSURE STUDIES/ Tested at 10% in petrolatum, ... /gamma-nonalactone/ produced no irritation after a 48 hr closed-patch test on human subjects.

gamma-Nonalactone 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 b) 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.

Based on the reviews of the generic data for the furanone active ingredients, the Agency has sufficient information on the health effects of furanone and on its potential for causing adverse effects in fish and wildlife and the environment. The Agency has determined that furanone products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. Therefore, the Agency concludes that all uses of products containing furanone are eligible for reregistration.