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5-Hydroxymethylfurfural

Product Name
5-Hydroxymethylfurfural
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
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5-Hydroxymethylfurfural Property

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
pka
12.82±0.10(Predicted)
form 
Liquid or Crystalline Powder and/or Chunks
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)
NIST Chemistry Reference
2-Furancarboxaldehyde, 5-(hydroxymethyl)-(67-47-0)
EPA Substance Registry System
2-Furancarboxaldehyde, 5-(hydroxymethyl)- (67-47-0)
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Safety

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
Hazardous Substances Data
67-47-0(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 2500 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H227Combustible liquid

H303May be harmfulif swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.20678
Product name
5-Hydroxymethyl-2-furancarbaldehyde
Purity
for synthesis
Packaging
100 mg
Price
$22.2
Updated
2021/12/16
Sigma-Aldrich
Product number
8.20678
Product name
5-Hydroxymethyl-2-furancarbaldehyde
Purity
for synthesis
Packaging
1 g
Price
$41.16
Updated
2021/12/16
Sigma-Aldrich
Product number
W501808
Product name
5-(Hydroxymethyl)furfural
Purity
≥99%, FG
Packaging
1 g
Price
$60
Updated
2021/12/16
Sigma-Aldrich
Product number
H40807
Product name
5-Hydroxymethyl-2-furaldehyde
Purity
99%
Packaging
1g
Price
$66.1
Updated
2021/12/16
Sigma-Aldrich
Product number
8.20678
Product name
5-Hydroxymethyl-2-furancarbaldehyde
Purity
for synthesis
Packaging
5 g
Price
$150.77
Updated
2021/12/16
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5-Hydroxymethylfurfural Chemical Properties,Usage,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.
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.

Uses

An antioxidant for grape and apple juice.

Uses

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

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

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.

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.

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

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5-Hydroxymethylfurfural Suppliers

Zhejiang Tangneng Technology Co., Ltd.
Tel
0574-55878979
Email
zhoujingjing@sugarenergy.com
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China
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Alfa Aesar
Tel
400-610-6006; 021-67582000
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
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China
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Shanghai Worldyang Chemical Co.,Ltd.
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021-56795766
Fax
+86-21-56795266
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sales@worldyachem.com
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Suzhou Guide Fine Material Co.Ltd.
Tel
0512-66627360-8004;0512-66627360-8008
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0512-66627360
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sales@guide-chemicals.com;lixm@guide-chemicals.com
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Shanghai TongYuan Chemical Co., Ltd.
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021-69182866
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021-69182022
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tongyuanchem@126.com
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China
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T&W GROUP
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021-61551611
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+86 21-50676805
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contact@trustwe.com
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China
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Suzhou Runsen Pharmaceutical Technology Co., Ltd.
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0512-65885589- ;
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0512-65885589
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sales@rosun-chemical.com;sales@rosun-chemical.com
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China
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Zhongke Guosheng (Hangzhou) Technology Co., LTD
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Email
wei.chen@guoshengtech.com
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China
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J & K SCIENTIFIC LTD.
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010-82848833- ;010-82848833
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86-10-82849933
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jkinfo@jkchemical.com;market6@jkchemical.com
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China
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Meryer (Shanghai) Chemical Technology Co., Ltd.
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+86-021-61259100
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86-21-61259102
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int02@meryer.com
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China
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View Lastest Price from 5-Hydroxymethylfurfural manufacturers

Baoji Guokang Bio-Technology Co., Ltd.
Product
5-Hydroxymethylfurfural 67-47-0
Price
US $142.00/g
Min. Order
100g
Purity
98%
Supply Ability
100kg
Release date
2021-06-04
Wuhan wingroup Pharmaceutical Co., Ltd
Product
5-hydroxymethylfurfural 67-47-0
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1000MT/Month
Release date
2021-07-16
Baoji Guokang Healthchem co.,ltd
Product
5-Hydroxymethylfurfural 67-47-0
Price
US $1208.00/KG
Min. Order
1KG
Purity
99
Supply Ability
10T
Release date
2021-06-07

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