5-Methylfurfural

5-Methylfurfural
Names
IUPAC name
5-Methylfuran-2-carbaldehyde
Other names
  • 5-Methyl-2-furaldehyde
  • 2-Furancarboxaldehyde, 5-methyl-
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.658 Edit this at Wikidata
EC Number
  • 210-622-6
KEGG
UNII
  • InChI=1S/C6H6O2/c1-5-2-3-6(4-7)8-5/h2-4H,1H3
    Key: OUDFNZMQXZILJD-UHFFFAOYSA-N
  • CC1=CC=C(O1)C=O
Properties
C6H6O2
Molar mass 110.112 g·mol−1
Density 1.098-1.108 g/mL (20 °C)
Boiling point 187 °C (369 °F; 460 K)
3.3 g/100mL
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

5-Methylfurfural is an organic compound with the formula C6H6O2. An aldehyde that is derived through various extractions and reductions from cellulose products, it has applications as a synthetic intermediate relevant to the fields of medicine, agriculture and cosmetics. It is a food additive, and has FEMA number 270s and JECFA number 745. Reduction of 5-methylfurfural gives the product 5-methylfurfuryl alcohol.

Synthesis

The synthesis of 5-methylfurfural has been documented from as early as 1891. It was originally synthesized from rhamnose, but can be produced from the dehydration of sucrose and other cellulose products. Several synthetic pathways have been proposed from 5-hydroxymethylfurfural. The compound has been produced in the 21st century using the historical precursor of rhamnose with the aim to use it as a precursor to biogasoline.

References

  1. ↑ "2-Furancarboxaldehyde, 5-methyl-". NIST Chemistry WebBook, SRD 69. 2023.
  2. 1 2 "Online Edition: "Specifications for Flavourings"". Food and Agriculture Organization of the United Nations. 2002. Retrieved June 25, 2024.
  3. 1 2 Zeitsch, Karl J., ed. (2000). "P. Properties of 5-methyl furfural". the chemistry and technology of furfural and its many by-products. Sugar Series. Vol. 13. Elsevier. p. 254. doi:10.1016/S0167-7675(00)80049-4. ISBN 978-0-444-50351-0. ISSN 0167-7675.
  4. ↑ "5-Methylfurfural". pubchem.ncbi.nlm.nih.gov.
  5. 1 2 "5-METHYLFURFURAL". Organic Syntheses. 14: 62. 1934. doi:10.15227/orgsyn.014.0062.
  6. ↑ Moe, Størker T.; Marcotullio, Gianluca; Opedal, Mihaela Tanase; Brusletto, Rune (December 2022). "Formation of 5-methylfurfural and 2-acetylfuran from lignocellulosic biomass and by Cr3+-catalyzed dehydration of 6-deoxyhexoses". Carbohydrate Research. 522 108672. doi:10.1016/j.carres.2022.108672. hdl:11250/3055856. PMID 36183617.
  7. 1 2 Li, Shaopeng; Dong, Minghua; Yang, Junjuan; Cheng, Xiaomeng; Shen, Xiaojun; Liu, Shulin; Wang, Zhi-Qiang; Gong, Xue-Qing; Liu, Huizhen; Han, Buxing (January 26, 2021). "Selective hydrogenation of 5-(hydroxymethyl)furfural to 5-methylfurfural over single atomic metals anchored on Nb2O5". Nature Communications. 12 (1): 584. doi:10.1038/s41467-020-20878-7. ISSN 2041-1723. PMC 7838200. PMID 33500400.
  8. 1 2 Peng, Yang; Li, Xianghua; Gao, Tian; Li, Teng; Yang, Weiran (2019). "Preparation of 5-methylfurfural from starch in one step by iodide mediated metal-free hydrogenolysis". Green Chemistry. 21 (15): 4169–4177. doi:10.1039/C9GC01645G. ISSN 1463-9262.
  9. ↑ Spillman, Philip J.; Pollnitz, Alan P.; Liacopoulos, Dimitra; Pardon, Kevin H.; Sefton, Mark A. (1998-02-01). "Formation and Degradation of Furfuryl Alcohol, 5-Methylfurfuryl Alcohol, Vanillyl Alcohol, and Their Ethyl Ethers in Barrel-Aged Wines". Journal of Agricultural and Food Chemistry. 46 (2): 657–663. doi:10.1021/jf970559r. ISSN 0021-8561. PMID 10554294.
  10. ↑
  11. ↑ Feng, Yunchao; Li, Zheng; Long, Sishi; Sun, Yong; Tang, Xing; Zeng, Xianhai; Lin, Lu (2020). "Direct conversion of biomass derived l -rhamnose to 5-methylfurfural in water in high yield". Green Chemistry. 22 (18): 5984–5988. doi:10.1039/D0GC02105A. ISSN 1463-9262.