(±)-γ-Nonalactone

156.22

156.22

203-219-1

46099|24253

DTXSID0034229

Colorless to slightly yellow liquid

29322090

26.3

2.2

Liquid

0.9513 g/cm³ @ Temp: 22 °C

243 °C

>230 °F

n 20/D 1.447(lit.)

soluble in five volumes of 50% alcohol; soluble in most fixed oils and mineral oil; practically insoluble in glycerol

Store below +30°C.

1.18X10-2 mm Hg at 25 deg C (est)

Strong odor reminiscent of coconut

Taste characteristics at 10 ppm: coconut, creamy, waxy with fatty milky notes

Acid value max: 2.0

Henry's Law constant = 1.7x10-4 atm-cu m/mol at 25 °C (est)

Combustible|Hydroxyl radical reaction rate constant = 9.69X10-12 cu cm/molec-sec at 25 °C (est)

NONH for all modes of transport

1

24/25-22

LU3675000

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

H315

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.

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.

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Furanone, EPA 738-R-96-009 (June 1996). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the USA.[Available from, as of September 22, 2015: http://www.epa.gov/pesticides/reregistration/status.htm]

Not Classified

Combustible liquid.

A skin irritiant.

Dihydro-5-pentyl-2(3H)-furanone was detected, but not quantified, in leachate produced in the acidification stage collected from a 9 year old part of the waste tip of Ambt-Delden in the eastern part of The Netherlands(1).

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.

LD50: Rat (male) oral 6600 mg/kg bw|LD50: Rat oral 9780 mg/kg bw|LD50: Rat oral > 5000 mg/kg bw.|LD50: Rabbit dermal > 5000 mg/kg bw|For more Non-Human Toxicity Values (Complete) data for DIHYDRO-5-PENTYL-2(3H)-FURANONE (6 total), please visit the HSDB record page.

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).

Dihydro-5-pentyl-2(3H)-furanone's production and use in perfumery and flavoring(1) 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 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).

The rate constant for the vapor-phase reaction of dihydro-5-pentyl-2(3H)-furanone with photochemically-produced hydroxyl radicals has been estimated as 9.7X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 40 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). By analogy to gamma-butyolactone, which exhibits a hydrolysis half-life of approximately 28 days at pH7(2), dihydro-5-pentyl-2(3H)-furanone is expected to undergo hydrolysis in the environment(SRC). Dihydro-5-pentyl-2(3H)-furanone contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 11 was calculated in fish for dihydro-5-pentyl-2(3H)-furanone(SRC), using an estimated log Kow of 2.08(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low (SRC).

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.

The Henry's Law constant for dihydro-5-pentyl-2(3H)-furanone is estimated as 1.7X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dihydro-5-pentyl-2(3H)-furanone is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 10 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 7 days(SRC). 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(SRC), determined from a fragment constant method(3).

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).

ENVIRONMENTAL: Dihydro-5-pentyl-2(3H)-furanone is reported present in camembert cheese, butter and milk(1).

According to the 2012 TSCA Inventory Update Reporting data, 9 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of dihydro-5-pentyl-2(3H)-furanone in the United States may be as low as <10 workers and as high as 99 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 11,047 workers (4,717 of these are female) were potentially exposed to dihydro-5-pentyl-2(3H)-furanone in the US(1). Occupational exposure to dihydro-5-pentyl-2(3H)-furanone may occur through dermal contact with this compound at workplaces where dihydro-5-pentyl-2(3H)-furanone is produced or used. Monitoring data indicate that the general population may be exposed to dihydro-5-pentyl-2(3H)-furanone via ingestion of food containing dihydro-5-pentyl-2(3H)-furanone. Use data indicate that the general population may be exposed to dihydro-5-pentyl-2(3H)-furanone via dermal contact with consumer products containing dihydro-5-pentyl-2(3H)-furanone(SRC).

The degree of breakdown of gamma-nonalactone under in vitro digestion was determined using rat liver homogenate. It is seen that there are marked difference between the three lactones with respect to the ease of ring cleavage. While both gamma-valerolactone and gamma-nonalactone opened rather readily, at pH 7.5, the gamma-undecalactone is more resistant to the enzymes of rat liver homogenate.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Ketones and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . For contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) 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. Administer activated charcoal ... . /Ketones and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ketones and related compounds/

/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.

Technical, FCC|Trade names Abricolin (Haarmann & Reimer), Prunolide (Givaudan)

All other chemical product and preparation manufacturing|2(3H)-Furanone, dihydro-5-pentyl-: ACTIVE|Concentration in final product as reported as percentage ranges from 0.005 usual to 0.1 maximum in soaps; 0.0005 usual to 0.01 maximum in detergents; 0.002 usual to 0.04 maximum in creams, lotions; and 0.04 to 1.0 maximum in perfumes. /From table/

Analytical data /determined by spectrophotometry/, infra-red curve: RIFM number 72.41.|Gamma-nonalactone was identified in peach oil by gas chromatography.

EPA Safer Chemical Functional Use Classes -> Fragrances|Safer Chemical Classes -> Green half-circle - The chemical is expected to be of low concern|Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fatty Acyls [FA] -> Fatty esters [FA07] -> Lactones [FA0704]|Cosmetics -> Solvent

Flavoring Agents