Furaneol

128.13

128.13

222-908-8

DTXSID0041517

Beige powder|Colorless crystals

2932190090

46.5

0.7

Solid

1.3±0.1 g/cm3

70 °C

188 °C

>230 °F

1.513

soluble in oil and ethanol

2-8°C

0.008 mm Hg at 25 deg C

3.3 (Air = 1)

Relatively weak, nonspecific odor; dilute solutions develop a pineapple, strawberry-like odor

Caramel flavor

Henry's Law constant = 1.5X10-5 atm-cu m/mole at 25 °C

pKa = 8.56 at 20 °C

Hydroxyl radical reaction rate constant = 1.4X10-10 cu cm/molec-sec at 25 °C (estimated)|Ozone reaction rate constant = 5.7X10-17 cu cm/molec-sec at 25 °C (estimated)

NONH for all modes of transport

3

22

36-24/25

LU3990000

Xn

Stable under recommended storage conditions.

P261, P264, P270, P272, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P333+P313, P337+P313, P363, P501

H302

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.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.

Incompatible materials: Strong oxidizing agents

WHO/JEFCA; WHO Food Additives Series 54 (2006)[Available from, as of May 27, 2016: http://www.inchem.org/pages/jecfa.html]

|Warning|H302 (28.22%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P333+P313, P337+P313, P363, and P501|Aggregated GHS information provided by 1826 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501

Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

A flammable liquid.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Do not let product enter drains.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Dimethylhydroxy furanone has been tested as a tobacco ingredient for cigarettes(1) and has been identified as a cigarette additive(2).

IDENTIFICATION AND USE: Dimethylhydroxy furanone is a beige powder. It is used as a flavoring agent and experimental medication. HUMAN EXPOSURE AND TOXICITY: 2,5-Dimethyl-4-hydroxy-3(2H)-furanone (2,5-DMHF), a caramel-like fragrant compound found in many processed foodstuffs, has been reported to be mutagenic. 2,5-DMHF generates superoxide and subsequently hydrogen peroxide to induce metal-dependent DNA damage. ANIMAL STUDIES: Groups of 60 male and 60 female rats were given diets containing 2,5-DMHF at a dose of 0 (control), 100, 200 or 400 mg/kg bw per day for 24 months. No significant compound-related effects were reported in any of the animals at 100 and 200 mg/kg bw per day. The mean body weights and body-weight gains of males and females at the highest dose (400 mg/kg bw per day) were significantly lower than those of control animals at 24 months. The mean survival rate for males in the group receiving the highest dose was significantly lower (approximately 20%, p<0.05) than that of males in the control group at 24 months. The authors concluded that this finding was attributable to an increased incidence of adenomas of the pars distalis of the pituitary, with subsequent compression of the hypothalamic region within the brains of males at the highest dose. It was concluded that these adenomas were common, spontaneous tumors that were unrelated to the administration of 2,5-DMHF. 2,5-DMHF showed mutagenicity to Salmonella typhimurium TA100 strain with and without metabolic activation, and induced micronucleated mouse peripheral reticulocytes. 2,5-DMHF induced micronucleated reticulocytes in mouse peripheral blood in a dose-dependent manner after oral administration /at doses of 0.5-1.0 g/kg/. The results indicate that DMHF can cause genetic damage after oral administration.

2,5-Dimethyl-4-hydroxy-3(2 H)-furanone (DMHF), produced by Maillard reaction of sugar/amino acid and found in various foodstuffs, showed mutagenicity to Salmonella typhimurium TA100 strain with and without S9 mix, and induced micronucleated mouse peripheral reticulocytes. DNA strand breaking activity of the compound at pH 7.4 increased with the increasing dose of the compound and with the increasing incubation time. The breaking activity was inhibited in the presence of superoxide dismutase, catalase, hydroxyl radical scavengers, spin trapping agents, thiol compounds and metal chelators, and also by removal of dissolved oxygen from the incubation mixture. Addition of Fe(III) ion to the incubation mixture enhanced the breaking activity. Incubation of DMHF with 5,5-dimethyl-1-pyrroline N-oxide (DMPO) gave electron spin resonance signals characteristic to DMPO-OH adduct, indicating generation of hydroxyl radical. It was found that DMHF generated hydroxyl radical with an aid of a trace amount of metal ions, and induced DNA strand breaking. Mutagenicity and induction of micronucleated reticulocytes by DMHF may be caused as a result of DNA modification via hydroxyl radical.|Prooxidant properties of furanone compounds including 2,5-furanone (furaneol, 4-hydroxy-2,5-dimethyl-furan-3-one), 4,5-furanone (4,5-dimethyl-3-hydroxy-2(5H)-furanone) (sotolone) and cyclotene (2-hydroxy-3-methyl-2-cyclopenten-1-one) were analyzed in relation to the metal-reducing activity. Only 2,5-furanone known as a "strawberry or pineapple furanone" inactivated aconitase the most sensitive enzyme to active oxygen in the presence of ferrous sulfate, suggesting the furaneol/iron-mediated generation of reactive oxygen species. 2,5-Furanone caused strand scission of pBR322 DNA in the presence of copper. Treatment of calf thymus DNA with 2,5-furanone plus copper produced 8-hydroxy-2'-deoxyguanosine in DNA. 2,5-Furanone showed a potent copper-reducing activity, and thus, DNA strand breaks and the formation of 8-hydroxy-2'-deoxyguanosine by 2,5-furanone can be initiated by the production of superoxide radical through the reduction of cupric ion to cuprous ion, resulting in the conversion to hydrogen peroxide and hydroxyl radical. However, an isomer and analog of 2,5-furanone, 4,5-furanone and cyclotene, respectively, did not show an inactivation of aconitase, DNA injuries including strand breakage and the formation of 8-hydroxy-2'-deoxyguanosine, and copper-reducing activity. Cytotoxic effect of 2,5-furanone with hydroxyketone structure can be explained by its prooxidant properties: furaneol/transition metal complex generates reactive oxygen species causing the inactivation of aconitase and the formation of DNA base damage by hydroxyl radical.

LD50 Mouse oral 1608 mg/kg

Dimethylhydroxy furanone was first identified in pineapples in 1965 and has been isolated from many different fresh fruits such as strawberry, raspberry, tomato, kiwi, lychee, and snake fruit(1). Dimethylhydroxy furanone was detected in the sex pheromone of the wingless cockroach Eurycotis floridana (Polyzosteriinae)(2).

Dimethylhydroxy furanone's production and use in the flavoring of foods(1), including pineapple and strawberry flavors(2), and use as a cigarette additive(3) 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 1(SRC), determined from a structure estimation method(2), indicates that dimethylhydroxy furanone is expected to have very high mobility in soil(SRC). Volatilization of dimethylhydroxy furanone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.5X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Dimethylhydroxy furanone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.008 mm Hg at 25 °C(SRC), determined from a fragment constant method(2); however, dimethylhydroxy furanone does emit an odor(3) even though it exists as a solid. Biodegradation data in soil were not available(SRC, 2016).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that dimethylhydroxy 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 1.5X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 and 25 days, respectively(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow of 0.95(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(3). Dimethylhydroxy furanone is an olefinic compound and olefins in surface waters exposed to sunlight react with photo-oxidants with a half-life on the order of 25 days(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethylhydroxy furanone, which has an estimated vapor pressure of 0.008 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 dimethylhydroxy 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 3 hours(SRC), calculated from its rate constant of 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Vapor-phase dimethylhydroxy furanone is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 5 hours(SRC), calculated from its rate constant of 5.7X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Dimethylhydroxy furanone contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of dimethylhydroxy furanone with photochemically-produced hydroxyl radicals has been estimated as 1.4X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of dimethylhydroxy furanone with ozone has been estimated as 5.7X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). Dimethylhydroxy furanone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Dimethylhydroxy furanone does contain chromophores that absorb at wavelengths >290 nm(2) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Dimethylhydroxy furanone is an olefinic compound and olefins in surface waters exposed to sunlight react with photo-oxidants (such as hydroxyl radicals, peroxy radicals and singlet oxygen) with a half-life on the order of 25 days(3).

An estimated BCF of 3 was calculated in fish for dimethylhydroxy furanone(SRC), using a log Kow of 0.95(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).

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

The Henry's Law constant for dimethylhydroxy furanone is estimated as 1.5X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dimethylhydroxy 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 3 days(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 25 days(SRC). Dimethylhydroxy furanone's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Dimethylhydroxy furanone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.008 mm Hg(SRC), determined from a fragment constant method(1); however, dimethylhydroxy furanone does emit an odor(3) even though it exists as a solid.

Dimethylhydroxy furanone is a constituent of pineapple and strawberry aroma and is also found in other foods(1). Volatiles emitted from rice cakes from two commercial companies contained dimethylhydroxy furanone levels of 15 and 90 ppb respectively(2). Dimethylhydroxy furanone was detected in the volatiles of muskmelon fruit (C. melo L. Cv. Miyabi)(3). Dimethylhydroxy furanone was identified in volatiles from roasted chestnuts(4). The volatile compounds extracted from the red-skinned cultivar of rambutan, Jitlee (Nephelium lappaceum L.), a tropical fruit native to Southeast Asia, contained a dimethylhydroxy furanone concentration of 240.15 ug/L in the juice(5). Dimethylhydroxy furanone was detected in the aroma odorants from freshly prepared popcorn(6). It has been detected in both red and white wines(7). Dimethylhydroxy furanone is reported to occur in guava, grapes, pineapple, raspberry, staewberry fruit and jams, rye bread, Swiss cheese, boiled beef, beer, cocoa, coffee, tea, filberts, almonds, oatmeal, Arctic bramble, yellow passion fruit, mango, fermented soy sauce, malt and Cape gooseberry(8). Dimethylhydroxy furanone was detected in beef extract aroma(9) and in beer(10).

Dimethylhydroxy furanone contributes to the aroma of human breast milk and to milk products such as nonfat dry milk and sweet whey powder(1).

Occupational exposure to dimethylhydroxy furanone may occur through inhalation and dermal contact with this compound at workplaces where dimethylhydroxy furanone is produced or used. Monitoring data indicate that the general population may be exposed to dimethylhydroxy furanone via inhalation of volatiles and aromas from food, ingestion of food and beverages, and dermal contact with consumer products containing dimethylhydroxy furanone. (SRC)

/EXPL THER/ ... 4-Hydroxy-5-methyl-3(2H)-furanone (HMF) and 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) were administered individually in semipurified diet to female ICR mice previously treated with benzo[a]pyrene (1.5 mg/wk, orally for 4 wk) to initiate forestomach neoplasia. The mice were killed at 30 wk of age. Both furanones reduced forestomach neoplasms, with HDMF exhibiting more potency. The data indicate that HDMF and HMF ... inhibit carcinogenesis in this system by acting at the post-initiation stage.

2,5-Dimethyl-4-hydroxy-3[2H]furanone (Furaneol, DMHF) [3658-77-3], an important flavor constituent of strawberry fruit, was administered to four male and two female volunteers using fresh strawberries as a natural DMHF source. The amount excreted was determined by measuring urinary levels of DMHF and DMHF glucuronide. DMHF glucuronide was synthesized and the structure elucidated by mens of (1)H, (13)C and two dimensional nuclear magnetic resonance, as well as mass spectral data. Identification and quantification of DMHF glucuronide in human urine were achieved after solid phase extraction on XAD-2 using reverse-phase reverse-phase HPLC with either on-line UV/VIS or electrospray tandem mass spectrometry detection. Male and female volunteers excreted 59-69% and 81-94%, respectively, of the DMHF dose (total of free and glycosidically bound DMHF in strawberries) as DMHF glucuronide in urine within 24 hr. The amount of DMHF excretion was independent of the dose size and the ratio of free to glycosidically bound forms of DMHF in strawberry fruit. DMHF, DMHF glucoside and its 6'-O-malonyl derivative, naturally occurring in strawberries, were not detected in human urine.|Fragrant hydroxyfuranone and dihydroxypyranone derivatives generated in the Maillard reaction of sugars and amino acids are detected in various processed foods and have been shown active to break DNA single-strand in the in vitro studies. In the present study, absorption of 2,5-dimethyl-4-hydroxy-3(2 H)-furanone (DMHF) and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2 H)-furanone (HEMF), both found in soy sauce, into plasma after a single intraperitoneal or oral administration at doses of 0.5-1.0 g/kg to mice was examined. Both compounds appeared in plasma 15 min after intraperitoneal administration and disappeared 2 hr after the administration. They appeared in plasma 5 min after oral administration, reached maximum after 15-45 min, and gradually disappeared after 2 h, indicating that they are absorbed by the digestive tract. Both DMHF and HEMF induced micronucleated reticulocytes (MNRETs) in mouse peripheral blood in a dose-dependent manner after oral administration. The results indicate that DMHF and HEMF can cause genetic damage after oral administration.|4-Hydroxy-2,5-dimethyl-3(2H)-furanone is expected to share the same metabolic fate as the primary material, i.e. conjugation with glucuronic acid and excretion in the urine.

4-Hydroxy-2,5-dimethyl-3(2H)-furanone is expected to share the same metabolic fate as the primary material, i.e. conjugation with glucuronic acid and excretion in the urine.

/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 if 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. /Poisons A and B/|/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 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 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/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 as necessary ... . Start IV administration of D5W TKO. 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 ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/GENOTOXICITY/ 2,5-Dimethyl-4-hydroxy-3(2H)-furanone (2,5-DMHF), a caramel-like fragrant compound found in many processed foodstuffs, has been reported to be mutagenic. 4,5-Dimethyl-3-hydroxy-2(5H)-furanone (4,5-DMHF), which is a similar characteristic fragrant compound, has no report concerning its mutagenicity. DNA damage by 2,5-DMHF and 4,5-DMHF was investigated by using DNA fragments obtained from the /human/ p53 tumor suppressor gene. 2,5-DMHF induced DNA damage extensively in the presence of Cu(II), but only slightly in the presence of Fe(III). 4,5-DMHF did not cause metal-dependent DNA damage. Bathocuproine, a Cu(I)-specific chelator, and catalase inhibited DNA damage induced by 2,5-DMHF plus Cu(II), whereas free hydroxyl radical scavengers did not. The order of DNA cleavage sites was thymine, cytosine>guanine residues. The site-specific DNA damage and effects of scavengers show that DNA-copper-oxygen complex rather than free *OH are involved in the DNA damage. Formation of 8-oxodeoxyguanosine (8-oxodG) by 2,5-DMHF increased with its concentration in the presence of Cu(II), whereas 8-oxodG formation increased only slightly in the presence of Fe(III). Degradation of 2,5-DMHF was efficiently accelerated by Cu(II), but only slightly accelerated by Fe(III). The degradation of 4,5-DMHF was little even in the presence of metal ions. Examination using cytochrome c suggests that superoxide was generated from 2,5-DMHF. Stoichiometric study of Cu(II) reduction revealed that autoxidation of 2,5-DMHF could offer 4-electron reduction. These results suggest that, at least in vitro and in an acellular system, 2,5-DMHF generates superoxide and subsequently hydrogen peroxide to induce metal-dependent DNA damage.

2,5-dimethyl-4-hydroxy-3(2H)-furanone

3(2H)-Furanone, 4-hydroxy-2,5-dimethyl-: ACTIVE

High-flow dynamic headspace sampling with excess anhydrous sodium sulfate was found to be an effective method of isolating Furaneol from fresh tomatoes. Quantitative analysis was carried out by gas chromatography using maltol as internal standard. ...|A unified sample preparation and modified chromatographic procedure were developed to determine two major off-flavors in orange juice, p-vinylguaiacol (PVG) and 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF or Furaneol). Furaneol was quantified using the absorbance difference between 335 and 292 nm. This procedure helped identify Furaneol by suppressing an interfering peak that developed in juice during storage. The C18 solid phase extraction procedure isolated both PVG and Furaneol from orange juice into a single extract. A 30 min reversed-phase HPLC gradient method employing UV and fluorescence detectors in series was also developed for the determination of both off-flavors from a single injection. The ternary solvent system consisted of water, methanol, and acetonitrile. Recovery studies yielded mean recoveries of 99.9% +/- 2.3% for Furaneol (0.3, 1.0, and 10.0 ppm) and 100.0% +/- 1.2% for PVG (0.05, 2.0, and 5.0 ppm), thus demonstrating that the unified solid phase procedure quantitatively isolated both compounds.|The water-soluble volatile components of fresh tomatoes were isolated by liquid-liquid continuous ether extraction of filtered blended tomato and separated from non-volatiles by high flow dynamic headspace sampling, after careful evaporation of the ether. Capillary GCMS analysis identified the important aroma compound 2,5-dimethyl-4-hydroxy-3(2H)-furanone (furaneol) and the related compound 5-methyl-4-hydroxy-3(2H)-furanone occurring in the fresh tomato at concentrations of the order of 2 mg and 10 mg/kg of tomato respectively. From the odor threshold and concentration evidence it seems probable that Furaneol contributes to fresh and processed tomato aroma.|Furaneol [2,5-dimethyl-4-hydroxy-3(2H)-furanone] was identified in white wines obtained from different cultivars which were not Vitis vinifera. An extraction method with ethyl acetate and a GC-MS has been applied to evaluate levels of this compound in different white wines, Vitis vinifera and non-Vitis vinifera, coming from different origins. Sixty-five wines of various hybrid cultivars and more than an hundred wines in general were analyzed using this method. In white wines made with hybrid grapes still used in Europe, furaneol was detected in almost all cases. As some wines made from these grapes are forbidden in Europe, this method can be used for detecting certain "frauds". The influence of the vinification method on furaneol levels has been studied. In all cases, vinification with skin contact leads to a decrease in furaneol concentrations. Furaneol levels can be increased by using pectolytic enzymes with beta-glucosidic secondary activities.|A method for the analytical determination of sotolon [4,5-dimethyl-3-hydroxy-2(5H)-furanone], maltol [3-hydroxy-2- methyl-4H-pyran-4-one] and free furaneol [2,5-dimethyl-4-hydroxy-3(2H)-furanone] in wine has been developed. The analytes are extracted from 50 mL of wine in a solid-phase extraction cartridge filled with 800 mg of LiChrolut EN resins. Interferences are removed with 15 mL of a pentane-dichloromethane (20:1) solution, and analytes are recovered with 6 mL of dichloromethane. The extract is concentrated up to 0.1 mL and analyzed by GC-ion trap MS. ... Furaneol was determined by non-resonant fragmentation of the m/z 128 mother ion and subsequent analysis of the m/z 81 ion. The detection limits of the method are in all cases between 0.5 and 1 ug/L, well below the olfactory thresholds of the compounds. The precision of the method is in the 4-5% range for levels in wine around 20 ug/L. Linearity holds at least up to 400 ug/L, and is satisfactory in all cases. The recoveries of maltol and sotolon are constant (70 and 64%, respectively) and do not depend on the type of wine. On the contrary, in the case of furaneol, red wines show constant and high recoveries (97%), while the recoveries on white wines range between 30 and 80%. Different experiments showed that this behavior is probably due to the existence of complexes formed between furaneol and sulphur dioxide or catechols. Sensory experiments confirmed that the complexed forms found in white wines are not perceived by orthonasal olfaction, and that the furaneol determined by the method can be considered as the free and odor-active fraction

Food additives -> Flavoring Agents|Cosmetics -> Tonic

Flavoring Agents