104-61-0CCCCCC1CCC(=O)O1OALYTRUKMRCXNH-UHFFFAOYSA-Nγ-nonalactone has been reported in Citrullus lanatus with data available.
104-61-0、57084-16-9、82373-92-0DTXSID0034229CHEMBL1919350.958-0.966 at 25 °C
0.958-0.966
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
This chemical does not meet GHS hazard criteria for 99.6% (1722 of 1729) of all reports.
Not Classified
Aggregated GHS information provided per 1729 reports by companies from 8 notifications to the ECHA C&L Inventory.
Chemical: 2(3H)-Furanone, dihydro-5-pentyl-
Regulation (EC) No 1831/2003 (amended)
2(3H)-Furanone, dihydro-5-pentyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2(3H)-Furanone, dihydro-5-pentyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: Nonan-4-olide (EC: 203-219-1)
Dihydro-5-pentyl-2(3H)-furanone: Does not have an individual approval but may be used under an appropriate group standard
A mutagen and severe skin irritant; Causes somnolence and abnormal liver and kidney function tests in high-dose animal studies; [RTECS] Safe to use as a flavoring agent in food; ADI = 0-1.25 mg/kg/ bw; [JECFA] Absorbed quickly by oral dosing in rats, and excreted mainly in urine (~64%) and to lesser extent feces (~32%); Low toxicity in gavage studies with cats and rats; Not irritating to skin of rabbits or humans; Not sensitizing to skin of guinea pigs or humans; An eye irritant in rats; Increased liver weights (no accompanying histopathological changes) observed in 90 day gavage study with rats; No significant adverse effects in two generation study with rats; [European Commission] Caused no skin irritation or sensitization in 25 human volunteers (10% in petrolatum); No significant adverse effects observed in feeding studies with rats (studies ranging from two weeks to two years); [HSDB] Low acute oral, dermal, and inhalation toxicity; Not irritating to skin or eyes and not sensitizing to skin; [Reference #1] See Butyrolactone.
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.
Reportedly found in peaches, apricots, roasted barley, rum, and tomatoes; Used as flavoring and fragrance ingredient; [HSDB] Used in the US as insecticide, insect and mammal repellent, and mosquito larvicide; [Reference #1]
For dihydro-5-pentyl-2(3H)-furanone (USEPA/OPP Pesticide Code: 122301) there are 0 labels match. /SRP: Not registered for current 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./
Perfumery, flavors
Reported uses (ppm):
2023: 8,500,000 - <10,000,000 lb
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2(3H)-Furanone, dihydro-5-pentyl-. Aggregated National Production Volume: < 500,000 pounds.
Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 2(3H)-Furanone, dihydro-5-pentyl-. National Production Volume: 449,322 lb/yr.
By reacting methylacrylate and hexanol in the presence of ditertiarybutyl peroxide; by condensation of undecylenic acid and malonic acid by lactonization of nonenoic acid.
Wird geladen…
Soluble in alcohol, most fixed oils, propylene glycol; 1:1 in 60% alcohol
Soluble in five volumes of 50% alcohol; soluble in most fixed oils and mineral oil; practically insoluble in glycerol
soluble in alcohol, most fixed oils and propylene glycol; insoluble in water
1 ml in 5 ml 60% alcohol (in ethanol)
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]
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.
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.
Knoevenagel condensation of malonic acid with heptaldehyde, followed by ring closure, gives the fragrance gamma-nonanoic lactone.
/gamma-Nonalactone/ ... can be prepared in good yield in a one-step process by radical addition of primary fatty alcohols to acrylic acid, using di-tert-butyl peroxide as a catalyst. A patent claims a high yield when the reaction is carried out in the presence of alkali phosphates or alkali sulfates.
Technical, FCC
Trade names Abricolin (Haarmann & Reimer), Prunolide (Givaudan)
Fragrance Ingredients
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Cosmetics -> Solvent
Not Known or Reasonably Ascertainable
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/
Beschreibungγ-Nonalactone has a strong odor reminiscent of coconut and a fatty, peculiar taste. May be synthesized by reacting methylacry- late and hexanol in the presence of ditertiarybutyl peroxide; by condensation of undecylenic acid and malonic acid; by lactonizα- tion of nonenoic acid.
OccurrenceReported found in peaches, apricots, roasted barely, rum, tomato, currants, guava, raisin, papaya, peach, pineapple, blackberry, strawberry jam, asparagus, wheat and crispbread, Camembert cheese, butter, milk, 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, plum, plumcot, beans, mushroom, starfruit, fenugreek, mango, tamarind, rice, prickly pear, buckwheat, licorice, malt, wort, cherimoya, Bourbon vanilla, shrimp, nectarine, maté and sweet grass oil.
Verwenden(Gamma)-Nonalactone is a synthetic flavoring agent that is a colorless to yellow liquid of strong, coconut-like odor. It is soluble in most fixed oils, mineral oil, and propylene glycol. It is stable in acids and unstable in alkali and should be stored in glass, tin, or aluminum containers. It is used in coconut flavors and has application in gelatins, puddings, baked goods, candy, and ice cream at 11–55 ppm. It is also termed aldehyde c-18.
synthetischeBy reacting methylacrylate and hexanol in the presence of ditertiarybutyl peroxide; by condensation of undecylenic acid and malonic acid by lactonization of nonenoic acid