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5-Hydroxymethylfurfural

5-Hydroxymethylfurfural
5-Hydroxymethylfurfural structure
CAS No.
67-47-0
Chemical Name:
5-Hydroxymethylfurfural
Synonyms
HMF;5-HMF;-2-furaL;5-HydroxyMethy;5-(HydroxyMethyl)-;TIMTEC-BB SBB004259;Furfural Impurity 2;Hydroxymethyl Water;5-Oxymethylfurfurole;5-HydroMethylfurfural
CBNumber:
CB6266813
Molecular Formula:
C6H6O3
Formula Weight:
126.11
MOL File:
67-47-0.mol

5-Hydroxymethylfurfural Properties

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.)
Flash point:
175 °F
storage temp. 
2-8°C
form 
Liquid or Crystalline Powder and/or Chunks
pka
12.82±0.10(Predicted)
color 
Light yellow to yellow
Water Solubility 
Soluble in water, alcohol, ethyl acetate, acetone, dimethylformamide, benzene, ether and chloroform.
Sensitive 
Air & Light Sensitive
Merck 
14,4832
BRN 
110889
Stability:
Light Sensitive, Very Hygroscopic
InChIKey
NOEGNKMFWQHSLB-UHFFFAOYSA-N
CAS DataBase Reference
67-47-0(CAS DataBase Reference)
EWG's Food Scores
1
NIST Chemistry Reference
2-Furancarboxaldehyde, 5-(hydroxymethyl)-(67-47-0)
EPA Substance Registry System
2-Furancarboxaldehyde, 5-(hydroxymethyl)- (67-47-0)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H227-H412-H303-H335-H315-H319
Precautionary statements  P210-P264-P273-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P403+P235-P501-P261-P280a-P304+P340-P405-P501a-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38-52/53
Safety Statements  26-36-24/25
WGK Germany  2
RTECS  LT7031100
8-10
TSCA  Yes
HS Code  29321900
Toxicity LD50 orally in Rabbit: 2500 mg/kg

5-Hydroxymethylfurfural price More Price(68)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.20678 5-Hydroxymethyl-2-furancarbaldehyde for synthesis 67-47-0 100 mg $22.2 2021-12-16 Buy
Sigma-Aldrich 8.20678 5-Hydroxymethyl-2-furancarbaldehyde for synthesis 67-47-0 1 g $41.16 2021-12-16 Buy
Sigma-Aldrich W501808 5-(Hydroxymethyl)furfural ≥99%, FG 67-47-0 1 g $60 2021-12-16 Buy
Sigma-Aldrich H40807 5-Hydroxymethyl-2-furaldehyde 99% 67-47-0 1g $66.1 2021-12-16 Buy
Sigma-Aldrich 8.20678 5-Hydroxymethyl-2-furancarbaldehyde for synthesis 67-47-0 5 g $150.77 2021-12-16 Buy

5-Hydroxymethylfurfural Chemical Properties,Uses,Production

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.

Description

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; Item No. 14805), hydroxyl, alkyl, and superoxide radicals in cell-free assays (IC50s = 27.1, 22.8, 45, and 33.5 μM, respectively).

Chemical Properties

Beige Coloured Crystalline Solid

Uses

As an indicator for excess heat-treatment in sugar-containing food.

Uses

An antioxidant for grape and apple juice.

Uses

5-Hydroxymethyl-2-furaldehyde is used as an intermediate of OMBF (5,5'-oxydimethylenebis(2- furfural)), crown ethers. It is used in organic synthesis to prepare dialdehydes, glycols, ethers, amino alcohols and acetals. It acts as an antioxidant found in some fruit juices and caramel products.

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

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.

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

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

5-Hydroxymethylfurfural Preparation Products And Raw materials

Raw materials

Preparation Products


5-Hydroxymethylfurfural Suppliers

Global( 516)Suppliers
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View Lastest Price from 5-Hydroxymethylfurfural manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-11-30 5-Hydroxymethylfurfural
67-47-0
US $142.00 / g 100g 98% 100kg Baoji Guokang Bio-Technology Co., Ltd.
2021-11-08 5-hydroxymethylfurfural
67-47-0
US $10.00 / KG 1KG 99% 1000MT/Month Wuhan wingroup Pharmaceutical Co., Ltd
2021-11-02 5-Hydroxymethylfurfural
67-47-0
US $1208.00 / KG 1KG 99 10T Baoji Guokang Healthchem co.,ltd

5-Hydroxymethylfurfural Spectrum


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