홈MCP워크벤치Skills
홈워크벤치알림마이페이지
Huagongshe 오픈 프로젝트：[email protected]AI 접속: llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.7.8
돌아가기
Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
HCID 237332생성일: 2026년 10월 27일

5-하이드록시메틸-2-푸르알데하이드

5-하이드록시메틸-2-푸르알데하이드 · HMF · 5-HMF · 5-(HYDROXYMETHYL)FURFURAL · 2-Furancarboxaldehyde, 5-(hydroxymethyl)- · 5-HYDROXYMETHYL-2-FURFURAL · 5-(HYDROXYMETHYL)-2-FURALDEHYDE · 5-HYDROXYMETHYL-2-FURANCARBOXALDEHYDE

https://huagongshe.com/ko/chemical/237332

5-하이드록시메틸-2-푸르알데하이드 분자 구조식

식별자 및 물리적 특성

CAS No.67-47-0
분자식C6H6O3
평균 분자량126.11 g/mol
단동위원소 질량126.03169405 g/mol
SMILESO=Cc1ccc(CO)o1
InChIKeyNOEGNKMFWQHSLB-UHFFFAOYSA-N
PubChem CID237332
ChEMBLCHEMBL185885
ChEBICHEBI:412516
EC No.200-654-9
DTXSIDDTXSID3030428
현지명5-하이드록시메틸-2-푸르알데하이드

화학 및 물리적 성질

XLogP-0.6
극성 표면적50.4
수소 결합 공여자 수1
수소 결합 수용자 수3
회전 가능 결합 수2
무거운 원자 수9
형식 전하0
복잡도102
냄새Odor of chamomile flowers디프로필렌 글리콜 중 0.10%. 기름진 버터향 곰팡내 나는 왁스 같은 캐러멜향
맛Butter, caramel, musty
밀도1.2062 g/cu cm at 25 °C1.243 g/mL at 25 °C (lit.)
Color/FormCrystalline solid (needles)Needles (ethyl ether-petroleum ether)
용해도Freely soluble in methanol, ethanol, acetone, ethyl acetate, dimethylformamide. Soluble in ether, benzene, chloroform. Less soluble in carbon tetrachloride. Sparingly soluble in petroleum ether.Soluble in common organic solvents클로로포름(약간 용해됨), 에틸아세테이트(약간 용해됨), 메탄올(약간 용해됨)
끓는 점BP: 115 °C at 1 mm Hg114.00 to 116.00 °C. @ 1.00 mm Hg114-116 °C/1 mmHg (lit.)
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
녹는점31.5 °C35 - 35.5 °C28-34 °C (lit.) 28-34 °C (lit.)
증기압0.00528 [mmHg]
굴절률Index of refraction: 1.5627 at 18 °Cn20/D 1.562(lit.)
Heat of Combustion665 kcal/mol
Physical DescriptionSolid with an odor of chamomile flowersmp = 31.5 deg C[Merck Index] Beige or yellow hygroscopic solidmp = 32-35 deg C[Alfa Aesar MSDS]
인화점175 °F
저장 조건2-8°C
물리적 상태액체 또는 결정질 분말 및/또는 덩어리
pKa(산도 계수)12.82±0.10(Predicted)
색상밝은 노란색에서 노란색까지
향취 유형지방이 많은
생물학적 소스synthetic
용해도물, 알코올, 에틸 아세테이트, 아세톤, 디메틸포름아미드, 벤젠, 에테르 및 클로로포름에 용해됩니다.
Merck14,4832
BRN110889
헨리 상수1.8×104 mol/(m3Pa) at 25℃, HSDB (2015)
안정성감광성, 흡습성이 매우 높음
주요 응용향료 및 향
화장품 원료 기능피부 컨디셔닝 - 보습제항산화제피부 컨디셔닝 - 보습제피부 보호피부 컨디셔닝 - 기타
InChI1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2
InChIKeyNOEGNKMFWQHSLB-UHFFFAOYSA-N
SMILES[H]C(=O)c1ccc(CO)o1
LogP(분배 계수)-0.778 (est)
NIST2-Furancarboxaldehyde, 5-(hydroxymethyl)-(67-47-0)
EPA2-Furancarboxaldehyde, 5-(hydroxymethyl)- (67-47-0)

화학적 성질

Beige Coloured Crystalline Solid.Among the organic compounds that can be obtained from biomass, 5-Hydroxymethylfurfural (5-HMF) is one of the most interesting ones. 5-HMF is an organic compound derived from dehydration of certain sugars (hexoses). This yellow, low-melting solid is highly water-soluble. The molecule consists of a furan ring, containing both aldehyde and alcohol functional groups. HMF as natural substance has been identified in a wide variety of heat-processed foods including milk, fruit juices, spirits, honey, etc. HMF, which is derived from cellulose, is a potential "carbon-neutral" feedstock for a number of chemical substances.

안전 및 규제

GHS 분류This chemical does not meet GHS hazard criteria for 1.2% (4 of 344) of reports.WarningH315 (60.2%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (65.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (64.2%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H412 (70.9%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 344 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 4 of 344 reports by companies.There are 18 notifications provided by 340 of 344 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
규제 정보Chemical: 2-Furancarboxaldehyde, 5-(hydroxymethyl)-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 02-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33331Status: Cease Manufacture Update: 21-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/273032-Furancarboxaldehyde, 5-(hydroxymethyl)-: Does not have an individual approval but may be used under an appropriate group standard
유해성 요약No evidence of carcinogenicity in 2-year studies of mice and rats[NTP] A skin and strong eye irritant[Alfa Aesar MSDS] See Furfural.
Hazard Classes and CategoriesSkin Irrit. 2 (60.2%)Eye Irrit. 2 (65.1%)

용도

개요

5-Hydroxymethylfurfural (5-HMF) derived from sugars is the link between biomass and furan-based chemicals. With its various functional groups and associated reaction sites, this small molecule opens the door to a wide range of chemical modifications, which makes 5-HMF a versatile renewable building block.5-HMF is widely spread in food products and is formed in sugar containing food when exposed to heat. It is widely used as an indicator of quality in food products. It is also employed to indicate the adulteration of food products with acid converted invert syrups.

용도

An antioxidant for grape and apple juice.

일반 설명

5-(Hydroxymethyl)furfural is an organic compound, widely spread in food products and is formed in sugar containing food when exposed to heat. It is widely used as an indicator of quality in food products. It is also employed to indicate the adulteration of food products with acid converted invert syrups.

제조 및 합성 방법

제조 방법

5-Hydroxymethylfurfural (HMF) was synthesized from glucose in a slug flow capillary microreactor, using a combination of AlCl3 and HCl as the homogeneous catalyst in the aqueous phase and methyl isobutyl ketone as the organic phase for in-situ HMF extraction.Continuous synthesis of 5-hydroxymethylfurfural from glucose using a combination of AlCl3 and HCl as catalyst in a biphasic slug flow capillary microreactor

STOT SE 3 (64.2%)
Aquatic Chronic 3 (70.9%)
처리 방법SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 qualitypotential migration in soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations.
체내 부담Using a liquid chromatographic analysis method with UV detection, 300 urine samples were analyzed for 5-hydroxymethyl-2-furfuraldehyde (HMF). HMF was detected in urine as its metabolite 5-hydroxymethyl-2-furoic acid (HMFA) at concentrations ranging from 0-100 mg/L with most samples around 10 mg/L (1). HMFA was also detected in urine during a 24 hr Norwegian dietary recall study at a level of 28.6 mg/L which was slightly higher than the estimated HMF intake of 27.6 mg/L indicating alternative sources of exposure to HMF may be present(2). Unmetabolized HMF was detected in the urine of 7 volunteers following consumption of 20 grams of plum jam containing 24 mg of HMF. After 6 hours, 163 ug of HMF was excretedthis is equivalent to approximately 0.75% of the ingested HMF(3).
상호 작용Our previous study reported that co-administration of honey significantly increased the serum levels of glycyrrhetic acid (GA) after oral administration of glycyrrhizin (GZ) in rabbits. The components of honey are sucrose, glucose, fructose and 5-hydroxymethyl-furaldehyde (HMF). To clarify the causative component(s) in honey that altered the metabolic pharmacokinetics of GZ, rabbits were given GZ (150 mg /per/ kg) with and without glucose (5 g /per/ rabbit), fructose (5 g /per/ rabbit) and HMF (1 mg /per/ kg), respectively, in crossover designs. An HPLC method was used to determine concentrations of GZ and GA in serum as well as GA and 3-dehydroglycyrrhetic acid (3-dehydroGA) in feces suspension. A noncompartment model was used to calculate the pharmacokinetic parameters and analysis of variance was used for statistical comparison. Our results indicated that the area under curve (AUC) of GA was significantly increased by 29% when HMF was coadministered, whereas the pharmacokinetics of GZ and GA were not significantly altered by coadministration of glucose or fructose. An in-vitro study, using feces to incubate GZ and GA individually, indicated that HMF significantly inhibited the oxidation of GA to 3-dehydroGA and this may explain the enhanced GA absorption in-vivo. It was concluded that HMF is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo.Chemical analysis of several brands of peritoneal dialysis fluids (PD fluids) has revealed the presence of 2-furaldehyde, 5-HMF (5-hydroxymethylfuraldehyde), acetaldehyde, formaldehyde, glyoxal, and methylglyoxal. The aim of this study was to investigate if the in vitro side effects caused by glucose degradation products, mainly formed during heat sterilization, are due to any of these recently identified aldehydes. Cell growth media or sterile filtered PD fluids were spiked with different concentrations of thealdehydes. In vitro side effects were determined as the inhibition of cell growth of cultured mouse fibroblasts or stimulated superoxide radical release from human peritoneal cells. Our results demonstrate that the occurrences of 2-furaldehyde, 5-HMF, acetaldehyde, formaldehyde, glyoxal, or methylglyoxal in heat-sterilized PD fluids are probably not the direct cause of in vitro side effects. In order to induce the same magnitude of cell growth inhibition as the heat-sterilized PD fluids, the concentrations of 2-furaldehyde, glyoxal, and 5-HMF had to be 50 to 350 times higher than those quantified in the PD fluids. The concentrations of acetaldehyde, formaldehyde, and methylglyoxal observed in the heat-sterilized PD fluids were closer to the cytotoxic concentrations although still 3 to 7 times lower. Since none of these aldehydes caused in vitro toxicity at the tested concentrations, the toxicity found in PD fluids is likely to be due to another glucose degradation product, not yet identified. However, it is possible that these aldehydes may still have adverse effects for patients on peritoneal dialysis.The effect of water activity (aw 0.98, 0.84 and 0.60) and reaction temperature (100, 120, 140 and 160 degrees C) on the mutagenic activity of the Maillard reaction products in heated ribose-lysine and glucose-lysine model systems, was investigated. In the ribose-lysine system, heated at 100 °C, the mutagenic activity of the mixture increased as the water activity was lowered. On the contrary, no dependence between mutagenic activity and water activity was observed in the glucose-lysine system. At higher temperatures, in both systems, the presence in the browned mixtures of an antibacterial activity interfering with the bacterial mutagenicity assay was observed. Under all the conditions tested, the ribose-lysine system turned out to be the most reactive by producing higher levels of mutagens. Furthermore, in this system, the antimicrobial interference was more easily detectable. In the model systems used, the browning reaction mixtures were analysed for their absorption spectrum between 200-460 nm, and for the accumulation of furfurals. The results obtained showed that, at temperatures between 120 and 140 degrees C there is a correlation among reaction temperature, absorbance at 420 and around 280 nm, mutagenic activity of the mixture and the level of furfurals. Changes in the levels of furfurals can be related to changes in mutagenicity of the browned mixtures.Dietary casein cooked at 180 °C promotes the growth of aberrant crypt foci and colon cancer in rats initiated with azozymethane. We speculated that promotion was due to a product that could be extracted by a solvent, such as 5-hydroxymethyl-2-furaldehyde (HMF), with tumor promoting activity or the carcinogenic heterocyclic aromatic amines (HAA). This hypothesis was tested by extracting cooked casein with solvents and water The extracts were then 1) assayed by high-performance liquid chromatography for HMF and HAA, 2) measured for mutagenicity on a frame-shift-sensitive strain of Salmonella typhimurium, 3) fed for 100 days to azoxymethane-initiated rats to test the promoting effect on aberrant crypt foci. Data show that 1) no HMF or HAA was detected in cooked casein, 2) no mutagenicity was detected on strain TA98, with or without metabolic activation, and 3) promotion was not associated with the extracts but with the cooked casein residue...For more Interactions (Complete) data for 5-Hydroxymethyl-2-furfuraldehyde (6 total), please visit the HSDB record page.
생태독성 수치LC50Species: Daphnia magna (Water Flea) weight 4-5 mgConditions: freshwater, staticConcentration: 62000 ug/L for 24 hr (95% confidence interval: 53000-78000 ug/L) /formulation/Concentration: 34000 ug/L for 72 hr (95% confidence interval: 27000-43000 ug/L) /formulation/
환경 거동TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2(SRC), determined from a structure estimation method(2), indicates that 5-hydroxymethyl-2-furfuraldehyde (HMF) is expected to have very high mobility in soil(SRC). Volatilization of HMF from moist soil surfaces is not expected to be an important fate process(SRC)given an estimated Henry's Law constant of 5.41X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). HMF is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.28X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data in soil were not available(SRC, 2011).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2(SRC), determined from a structure estimation method(2), indicates that 5-hydroxymethyl-2-furfuraldehyde is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.41X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -0.09(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2011).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 5-hydroxymethyl-2-furfuraldehyde (HMF), which has an estimated vapor pressure of 5.28X10-3 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 HMF 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 0.2 days(SRC), calculated from its rate constant of 5.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). HMF absorbs light at wavelengths of 283 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).
식품 조사 수치Fifteen of sixteen commercial baby foods (3 milk-based and 13 cereal based) were reported to contain 5-hydroxymethyl-2-furfuraldehyde (HMF) at levels ranging from 0.17-57.18 ug/g. The results indicated that 8 of 13 baby foods contained HMF at concentrations <1.0 ug/g with all the milk-based products being in this group. The remaining cereal-based foods > 1 ug/g ranged from 1.04-5.00 ug/g with one much higher result reported as 57.18 ug/g (possibly due to precessing temperature)(1). In another survey of breakfast cereals, HMF was detected in a range of 3.67-193.34 ug/g among 23 samples of commercial cereals from 6 brands tested in Spain(2).5-Hydroxymethyl-2-furfuraldehyde (HMF)was detected in apple juice stored for 1 year. The reported concentrations correlated positively with storage temperature - about 1 mg/L at 3 °C for apples of different ripeness, 1.6 mg/L at 20 °C for juice from unripe apples and 6.7 mg/L at 20 °C for juice from ripe apples. A higher concentration of HMF was reported for stored apple juice made from ripe apples than from juice of unripe apples stored for the same length of time(1). In another study 4 out of 5 prune products analyzed contained HMF at levels ranging from 0.8-93.4 mg/100 mL. Fresh prune juice did not contain HMF and frozen juice from fresh prunes had the lowest value for HMF (0.8 mg/100 mL). Prune products undergoing processing had higher values93.4 mg/100 mL (dried prunes with pulp), 85.8 mg/100 mL (dried prunes without pulp), and 92.0 mg/100 mL (prune juice from concentrate(2). In another study HMF was detected in carbonated soft drinks (0.19-3.3 mg/kg), juices (0.6-75.5 mg/kg), fructose sachets (4.2 mg/kg), and Sudanese dates (147-310 mg/kg)(3). HMF was measured in commercial ground coffee and soluble coffee marketed in Spain. Levels of 110, 625, 1734, 2480 mg HMF/kg were obtained for natural, blend, torrefacto, and soluble coffee, respectively. The greatest variability of HMF was apparent in soluble coffee(4).Concentrated food products including 7 fruit concentrates, 17 boiled juices and 12 tomato and paprika pastes were analyzed for 5-hydroxymethyl-2-furfuraldehyde (HMF) and found to contain between 0.4 and 3500 ppm. Fruit concentrates contained 0.4-4.5 ppm, boiled juices 12.8-3500 ppm, and 0.4-18 ppm for tomato and paprika pastes(1). HMF was found in natural honey (2.3-798 mg/kg), commercial honey (11-614 mg/kg), and jams (26.1-807 mg/kg)(2). In another study the levels of HMF detected in samples of high fructose corn syrup supplied by beekeepers was 26.91-102.31 ppm and by manufacturers 11.09-33.8 ppm. The results were much more variable from the beekeepers(3). This compound has also been detected in caramel, which is a widely used coloring agent in food and pharmaceutical syrups. Although concentrations reported in pharmaceutical syrups is very low, there is some concern regarding the possibility of interaction between 5-Hydroxymethylfurfural and active drugs with amino functional groups(4).5-Hydroxymethyl-2-furfuraldehyde (HMF) is present in sherries and grape concentrate. Medium sherries were found to have concentrations in the range 20-340 ppmsweet sherries 130-680 ppm. Concentration increases with sugar content and baking time(1). Another study analyzed various vinegars for 5-hydroxymethyl-2-furfural and reported levels ranging from 0.2-3251 mg/L(2). Individual results in mg/L ranged from 1.6-7.3 (malt vinegar), 13.8-34.8 (sherry vinegar), 0.3-8.7 (white wine vinegar), 0.3-10.7 (red wine vinegar), 1.5-19.2 (apple vinegar), 0.2-9.0 (table vinegar with caramel), 316.4-3251.3 (balsamic vinegar)(2). In wine HMF was found at a level of 6.25 ug/L in the initial wine, at levels of 27.1-52.1 ug/L in wine aged 12 months in oak barrels, and 19.7-85.0 ug/L in wine aged 21 months in oak barrels(3).5-Hydroxymethyl-2-furfuraldehyde (HMF) formation was reported during the roasting of cocoa beans, toasting of bread, and baking of cookies. A cocoa bean roasting model system consisting of oxidized and nonoxidized cocoa butter reported HMF concentrations of 43.5 and 51.0 mg/kg respectively(1). A model bread made of three kinds of flour rye, wheat and whole wheat were investigated at toasting temperatures of 140, 160, and 180 °C. HMF concentration of untoasted was below the quantification limit (0.5 mg/kg). After toasting the breads at the highest temperature, (180 °C) the HMF concentrations reported were 46.69, 47.02, 17.25 mg/kg for rye, wheat and whole-wheat breads(2). Model cookies were baked at temperatures of 150, 200, and 300 °C and reported respective HMF concentrations of 0.3, 5 and 229 mg/kg dry basis when analyzed by HPLC(3). In commercial cookies, HMF was found at levels ranging from 0.5 to 74.6 mg/kg(4). HMF was also detected in popcorn at 100 ug/kg, (5) boiled Chinese chestnuts(6), and roasted earth-almonds (Cyperus esculentus L.)(7).
Milk ConcentrationsReducing sugars in milk, such as lactose, can form 5-hydroxymethyl-2-furfuraldehyde when it is treated at temperatures in excess of 120 °C(1).
Average Daily IntakeA study of hydroxymethyl-2-furfuraldehyde (HMF) exposure to the Spanish population from heat-processed food suggests the mean HMF intake was estimated to be 10 mg/day(-1) with coffee and bread being the most important food items, contributing nearly 85 percent to the total HMF daily exposure. Biscuits, breakfast cereals, beer, UHT milk and tomato products are also important for HMF exposure(1). Using a deterministic approach the dietary exposure to HMF via coffee consumption in the total Spanish population was estimated to be 8.57 mg/day but when specific contribution of each type of ground and soluble coffee in the consumption habits was considered it was estimated to be 5.26 mg HMF/day. A level of 8.57 mg HMF/day was calculated for persons with high consumption habits (95th percentile)(2). The daily dietary intake of HMF was determined using the HMF content in Norwegian food items and estimated the dietary intake of HMF in 53 volunteers by means of 24 h dietary recall. Coffee, prunes, dark beer, canned peaches, and raisins had the highest levels of HMF. The 95th percentile of the estimated daily dietary intake of HMF were 27.6 mg/day(3).
생태독성 발췌/OTHER TERRESTRIAL SPECIES/ Dimethyl malate (1) and 5-hydroxymethyl furfural (2) were isolated as insecticidal compounds by bioassay-guided fractionation from MeOH extract of the fruits of Cornus officinalis Sieb. et Zucc. /dowood/ Insecticidal activity against larvae of D. melanogaster /fruit fly/ was demonstrated: 1 and 2 gave the LC50 value of 6.15 and 11.8 umol/mL of diet concentration, respectively. Acute toxicity against adults of D. melanogaster, 1 and 2 had the insecticidal activity, with the LD50 value of 21.5 and 34.0 ug /per/ adult.
Effluent ConcentrationsIn a study of the organic composition of fine particle emissions from wood combustion, 5-hydroxymethyl-2-furfuraldehyde (HMF) was found in 5 out of 6 woods burned. The concentrations reported in mg/g organic carbon were 16.131, 14.388, 7.665, 16.901 for HMF in Northern red oak, paper birch, Eastern white pine, and balsam fir emissions respectively. HMF was detected but not quantified in Eastern hemlock emissions and not detected in red maple emissions(1). Hydroxymethylfurfural, isomer not specified, was detected in the particulate phase of wood combustion emissions with different airflow setups, with detections of 343, 911, and 1014 mg/kg dry wood burned reported, in an open, half-closed, and closed airflow configuration, respectively(2).
Soil Adsorption/MobilityUsing a structure estimation method based on molecular connectivity indices(1), the Koc of 5-hydroxymethyl-2-furfuraldehyde can be estimated to be 2(SRC). According to a classification scheme(2), this estimated Koc value suggests that 5-hydroxymethyl-2-furfuraldehyde is expected to have very high mobility in soil.
Natural Pollution Sources5-Hydroxymethyl-2-furfuraldehyde (HMF) was detected in apple juice(1), fresh prune juice(2), Sudanese dates(3) and in natural honey(4).
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ 5-Hydroxymethylfurfural has become a substance of interest since recent results showed a possible carcinogenic potential in consequence of a metabolic activation by sulfotransferases. 5-Hydroxymethylfurfural is formed either by acid catalysed degradation of reducing sugars or via the Maillard reaction. This work provides an overview of foods potentially containing high amounts of 5-hydroxymethylfurfural. It comprises dried fruits with a high sugar content that were exposed to heat for a long time. The concentration ranges from very low in, e. g. figs (1 mg/kg) to plums that contained up to 2,200 mg/kg. Several types of roasted coffee were analysed that contained from 300 to 2,900 mg/kg of 5-hydroxymethylfurfural. In a small human study with seven healthy volunteers the urine excretion of unmetabolised 5-hydroxymethylfurfural was investigated. After uptake of 20 g of plum jam containing 24 mg of 5-hydroxymethylfurfural, 163 ug (mean) were excreted within 6 hr, an equivalent of 0.75% of the ingested 5-hydroxymethylfurfural./GENOTOXICITY/ 5-Hydroxymethylfurfural (5-HMF) is known as an indicator of quality deterioration in a wide range of foods. 5-HMF is formed as an intermediate in the Maillard reaction and has been identified in a wide variety of heat-processed foods. In recent years, the presence of 5-HMF in foods has raised toxicological concerns: data have shown cytotoxic, genotoxic and tumoral effects but further studies suggest that 5-HMF does not pose a serious health risk. However the subject is still a matter of debate. /This study/ investigated the genotoxicity of the food-borne contaminant 5-HMF using the Ames test, the micronucleus (MN) and the single-cell gel electrophoresis (SCGE) assays in the human metabolically active HepG2 cell line. Cytotoxic effect of 5-HMF was first assessed using Alamar Blue as a sensitive sub-lethal assay. 5-HMF did not induce any ...mutation in bacteria whatever the concentration in the Ames test. Furthermore, it does not induce clastogenic or aneugenic effects in the HepG2 cells. In contrast, 5-HMF induced HepG2 DNA damage at concentrations from 7.87 to 25 mM in the comet assay suggesting a weak genotoxic effect of 5-HMF in the HepG2 cells probably repaired./GENOTOXICITY/ 5-Hydroxymethylfurfural (HMF), a heat-induced food toxicant present in a vast number of food items, has been suggested to be genotoxic after being bioactivated by the sulfotransferase SULT1A1. The comet assay was used to evaluate the DNA damaging effect of HMF in cell lines with different activities of SULT1A1: two human cell lines (Caco-2, low activityand HEK293, higher activity), one cell line from mouse (L5178Y, no activity) and two cell lines from Chinese hamster (V79, negligible activityand V79-hP-PST, high activity of human SULT1A1). HMF induced significant DNA damage in all cell lines after 3 hr exposure to 100 mM. Most sensitive were V79 and V79-hP-PST where HMF induced significant DNA damage at 25 mM. Consequently...the present study ... have shown that HMF is a DNA damaging agent in vitro independent of the activity of SULT1A1 in the cells. The HMF-induced DNA damage was only observed at rather high concentrations which usually was associated with a concomitant decrease in cell viability./GENOTOXICITY/ 5-(hydroxymethyl)-2-furfural (HMF), a common product of the Maillard reaction, occurs in many foods in high concentrations, sometimes exceeding 1 g/kg (in certain dried fruits and caramel products). The toxicological relevance of this exposure has not yet been clarified. Induction of aberrant colonic crypt foci had been reported for HMF, in vitro studies on genotoxicity/mutagenicity have given controversial results. To elucidate the toxic potential of HMF, cytotoxicity (trypan blue exclusion), growth inhibition (SRB assay), mutagenicity (HPRT assay), DNA damage (single-cell gel electrophoresis) and depletion of cellular glutathione were investigated in mammalian cells. Genotoxicity (SOS repair) was monitored in Salmonella typhimurium (umu assay). HMF induced moderate cytotoxicity in V79 cells (LC(50): 115 mM, 1 hr incubation) and in Caco-2 cells (LC(50): 118 mM, 1 hr incubation). Growth inhibition was monitored following 24 hr of incubation (V79, IC(50): 6.4 mM). DNA damage was detectable neither in these cell lines nor in primary rat hepatocytes up to the cytotoxic threshold concentration (75% absolute viability). Likewise, in primary human colon cells, obtained from biopsy material, DNA damage was not measurable. At 120 mM, already exhibiting some reduction in cell viability, HMF was weakly mutagenic at the hprt-locus in V79 cells (mutants/million cells: HMF 120 mM: 16 vs control: 3). Intracelluar glutathione was depleted by HMF (>or=50 mM) in V79 cells, in the human colon adenocarcinoma cell line Caco-2 and in primary rat hepatocytes down to approximately 30% of control (120 mM). Genotoxicity was observed with HMF in the umu assay without external activation (16 mM: 185 rel. umu units, %, P<0.001). The genotoxic potential was not altered by addition of rat liver microsomes. By comparison, the natural flavour constituent (E)-2-hexenal (HEX) was already cytotoxic, mutagenic and depleted glutathione at about 1000-fold lower concentrations. It inducedFor more Human Toxicity Excerpts (Complete) data for 5-Hydroxymethyl-2-furfuraldehyde (10 total), please visit the HSDB record page.
수질 위해 등급(WGK)2
TSCA 등재 상태TSCA listed
RTECS 번호LT7031100
독성LD50 orally in Rabbit: 2500 mg/kg
관세 코드29321900
위험 문구(R)36/37/38-52/53
위험 표시Xi
안전 문구(S)26-36-24/25
기존화학 물질KE-20648
F 고인화성물질8-10
위험 등급Eye Irrit. 2Skin Irrit. 2
저장 분류11 - Combustible Solids
유해 물질 데이터67-47-0(Hazardous Substances Data)