5-(Hydroxymethyl)-2-furaldehyd
HMF · 5-HMF · 5-(HYDROXYMETHYL)FURFURAL · 2-Furancarboxaldehyde, 5-(hydroxymethyl)- · 5-HYDROXYMETHYL-2-FURFURAL · 5-(HYDROXYMETHYL)-2-FURALDEHYDE · 5-HYDROXYMETHYL-2-FURANCARBOXALDEHYDE · HydroxyMethyl furfural
Identifikatoren & physikalische Daten
| CAS No. | 67-47-0 |
|---|---|
| Summenformel | C6H6O3 |
| Durchschnittliche Molmasse | 126,11 g/mol |
| Monoisotopische Masse | 126,03169405 g/mol |
| SMILES | O=Cc1ccc(CO)o1 |
| InChIKey | NOEGNKMFWQHSLB-UHFFFAOYSA-N |
| PubChem CID | 237332 |
| ChEMBL | CHEMBL185885 |
| ChEBI | CHEBI:412516 |
| EC No. | 200-654-9 |
| DTXSID | DTXSID3030428 |
| Lokaler Name | 5-(Hydroxymethyl)-2-furaldehyd |
Chemische & physikalische Eigenschaften
| XLogP | -0,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 50,4 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 102 |
| Geruch | Odor of chamomile flowers |
| Geschmack | Butter, caramel, musty |
| Dichte | 1.2062 g/cu cm at 25 °C1.243 g/mL at 25 °C (lit.) |
| Color/Form | Crystalline solid (needles)Needles (ethyl ether-petroleum ether) |
| Löslichkeit | Freely 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 solventsChloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)Soluble in water, alcohol, ethyl acetate, acetone, dimethylformamide, benzene, ether and chloroform. |
| Siedepunkt | BP: 115 °C at 1 mm Hg114.00 to 116.00 °C. @ 1.00 mm Hg114-116 °C/1 mmHg (lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | 31.5 °C35 - 35.5 °C28-34 °C (lit.) 28-34 °C (lit.) |
| Dampfdruck | 0.00528 [mmHg] |
| Brechungsindex | Index of refraction: 1.5627 at 18 °Cn20/D 1.562(lit.) |
| Heat of Combustion | 665 kcal/mol |
| Physical Description | Solid with an odor of chamomile flowersmp = 31.5 deg C[Merck Index] Beige or yellow hygroscopic solidmp = 32-35 deg C[Alfa Aesar MSDS] |
| Flammpunkt | 175 °F |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid or Crystalline Powder and/or Chunks |
| pKa (Säurekonstante) | 12.82±0.10(Predicted) |
| Farbe | Light yellow to yellow |
| Geruch | at 0.10 % in dipropylene glycol. fatty buttery musty waxy caramellic |
| Geruchsart | fatty |
| Biologische Quelle | synthetic |
| Merck | 14,4832 |
| BRN | 110889 |
| Henry-Konstante | 1.8×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Light Sensitive, Very Hygroscopic |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING - HUMECTANTANTIOXIDANTSKIN CONDITIONING - EMOLLIENTSKIN PROTECTINGSKIN CONDITIONING - MISCELLANEOUS |
| InChI | 1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2 |
| InChIKey | NOEGNKMFWQHSLB-UHFFFAOYSA-N |
| SMILES | [H]C(=O)c1ccc(CO)o1 |
| LogP (Verteilungskoeffizient) | -0.778 (est) |
| CAS Datenbank | 67-47-0(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Furancarboxaldehyde, 5-(hydroxymethyl)-(67-47-0) |
| EPA chemische Informationen | 2-Furancarboxaldehyde, 5-(hydroxymethyl)- (67-47-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | This 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. |
|---|---|
| Regulatorische Informationen | Chemical: 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 |
| Gefahrenübersicht | No 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 Categories |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
An antioxidant for grape and apple juice.
Herstellung & Synthese
synthetische
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