| Identification | More | [Name]
5-Hydroxymethylfurfural | [CAS]
67-47-0 | [Synonyms]
5-(HYDROXYMETHYL)-2-FURALDEHYDE
5-HYDROXYMETHYL-2-FURANCARBALDEHYDE
5-HYDROXYMETHYL-2-FURANCARBOXALDEHYDE
5-HYDROXYMETHYL-2-FURFURAL
5-HYDROXYMETHYL-2-FURFUROL
5-(HYDROXYMETHYL)FURFURAL
5-(HYDROXYMETHYL)FURFUROL
HMF
TIMTEC-BB SBB004259
2-Furaldehyde, 5-(hydroxymethyl)-
2-Hydroxymethyl-5-furfural
5-(Hyddroxymethyl)Furfurole
5-(Hydroxymethyl)-2-formylfuran
5-(hydroxymethyl)-2-furaldehyd
5-(Hydroxymethyl)-2-furancarbonal
5-(hydroxymethyl)-2-furancarboxaldehyd
5-(hydroxymethyl)-2-furfural (HMF)
5-(Hydroxymethyl)-2-furfuraldehyde
5-(Hydroxymethyl)furan-2-aldehyde
5-Hydroxymethylfuraldehyde | [EINECS(EC#)]
200-654-9 | [Molecular Formula]
C6H6O3 | [MDL Number]
MFCD00003234 | [Molecular Weight]
126.11 | [MOL File]
67-47-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Beige Coloured Crystalline Solid | [Melting point ]
28-34 °C (lit.)
28-34 °C (lit.) | [Boiling point ]
114-116 °C/1 mmHg (lit.) | [density ]
1.243 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.562(lit.)
| [Fp ]
175 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) | [form ]
Liquid or Crystalline Powder and/or Chunks | [pka]
12.82±0.10(Predicted) | [color ]
Light yellow to yellow | [Odor]
at 0.10 % in dipropylene glycol. fatty buttery musty waxy caramellic | [Odor Type]
fatty | [Water Solubility ]
Soluble in water, alcohol, ethyl acetate, acetone, dimethylformamide, benzene, ether and chloroform. | [Sensitive ]
Air & Light Sensitive | [Detection Methods]
HPLC,NMR | [Merck ]
14,4832 | [BRN ]
110889 | [Stability:]
Light Sensitive, Very Hygroscopic | [InChIKey]
NOEGNKMFWQHSLB-UHFFFAOYSA-N | [LogP]
-0.778 (est) | [CAS DataBase Reference]
67-47-0(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Furancarboxaldehyde, 5-(hydroxymethyl)-(67-47-0) | [Storage Precautions]
Light sensitive;Store under nitrogen | [EPA Substance Registry System]
67-47-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
2
| [RTECS ]
LT7031100
| [F ]
8-10 | [TSCA ]
Yes | [HS Code ]
29321900 | [Hazardous Substances Data]
67-47-0(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 2500 mg/kg |
| Hazard Information | Back Directory | [Description]
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. | [Chemical Properties]
Beige Coloured Crystalline Solid | [Uses]
An antioxidant for grape and apple juice. | [Uses]
As an indicator for excess heat-treatment in sugar-containing food. | [Application]
5-Hydroxymethylfurfural has been used as a standard in the high performance liquid chromatographic (HPLC) analysis for the determination of 5-(hydroxymethyl)furfural content in co-hydrolysates and fermentation broth of lignocellulosic biomass for the lipid accumulation in M. isabellina type of microorganisms. 5-(Hydroxymethyl)furfural may be used as an analytical reference standard for the quantification of the analyte in vinegar and fruit juice samples using chromatography techniques.
5-Hydroxymethylfurfural has been used as standard in the high performance liquid chromatographic (HPLC) analysis for the determination of 5-(hydroxymethyl)furfural content in co-hydrolysates and fermentation broth of lignocellulosic biomass for the lipid accumulation in M. isabellina type of microorganisms. | [Definition]
ChEBI: A member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and espec
ally by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo. | [Preparation]
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 | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 59, p. 7259, 1994 DOI: 10.1021/jo00103a016 | [General Description]
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. | [Biological Activity]
5-Hydroxymethylfurfural is a furanic compound derived from the degradation of sugars. It can be derived from reducing sugars via acid-catalyzed degradation or the Maillard reaction during the heating and storage of foods. 5-Hydroxymethylfurfural is an intermediate in the synthesis of a variety of compounds including 2,5-diformylfuran (DFF), 2,5-furandicarboxylic acid (FDA), 2,5-bis(hydroxymethyl)furan (5-(hydroxymethyl)furfuryl alcohol; Item No. 20658), and dimethylfuran (DMF), among others. 5-Hydroxymethylfurfural has been found in the marine algae L. undulata and scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH), hydroxyl, alkyl, and superoxide radicals in cell-free assays (IC50s = 27.1, 22.8, 45, and 33.5 μM, respectively). | [Safety Profile]
Questionable carcinogen with experimental tumorigenic data.Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES | [Safety]
5-Hydroxymethylfurfural is irritating to eyes, mucous membranes and skin, and has neurotoxicity and genotoxicity; it can be metabolized into 5-sulfoxymethylfurfural (SMF) in vivo, which has strong carcinogenicity and Genotoxicity. Chemical properties Light yellow waxy, easily soluble in methanol and ethanol, derived from Cornus, with high content of d-glucose. Uses for content determination/identification/pharmacological experiments, etc. | [Metabolic pathway]
When 5-hydroxymethyl-2-furaldehyde (HMF) is
administered orally or intravenously to rats, HMF or its
metabolites are rapidly eliminated in the urine with the
recovery of 95 ? 100% after 24 h. HMF is completely
converted to two metabolites which are identified as 5-
hydroxymethyl-2-furoic acid and N-(5-hydroxymethyl-2-
furoyl)glycine. | [Purification Methods]
Crystallise it from diethyl ether/pet ether. [Beilstein 18 III/IV 100, 18/1 V 130.] | [Toxicity evaluation]
5-Hydroxymethylfurfural (5-HMF) as a product of the Maillard reaction is found in many foods. Estimated intakes range between 4 and 30?mg per person and day, while an intake of up to 350?mg can result from, e.g., beverages made from dried plums. In vitro genotoxicity was positive when the metabolic preconditions for the formation of the reactive metabolite 5-sulphoxymethylfurfural were met. However, so far in vivo genotoxicity was negative. Results obtained in short-term model studies for 5-HMF on the induction of neoplastic changes in the intestinal tract were negative or cannot be reliably interpreted as “carcinogenic”. In the only long-term carcinogenicity study in rats and mice no tumours or their precursory stages were induced by 5-HMF aside from liver adenomas in female mice, the relevance of which must be viewed as doubtful. Hence, no relevance for humans concerning carcinogenic and genotoxic effects can be derived. The remaining toxic potential is rather low. Various animal experiments reveal that no adverse effect levels are in the range of 80–100?mg/kg body weight and day. Safety margins are generally sufficient. However, 5-HMF exposure resulting from caramel colours used as food additives should be further evaluated.
Toxicology and risk assessment of 5-Hydroxymethylfurfural in food |
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