5-Methylfurfuryl alcohol

5-Methylfurfuryl alcohol
Names
	IUPAC name (5-methylfuran-2-yl)methanol
	Other names 2-Furanmethanol, 5-methyl-; (5-Methylfur-2-yl)-methanol; Furfural propyleneglycol acetal;
Identifiers
CAS Number	3857-25-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	454366;
EC Number	672-135-9;
PubChem CID	520911;
UNII	0JVO5EFA0A;
	InChI InChI=1S/C6H8O2/c1-5-2-3-6(4-7)8-5/h2-3,7H,4H2,1H3 Key: VOZFDEJGHQWZHU-UHFFFAOYSA-N;
	SMILES CC1=CC=C(O1)CO;
Properties
Chemical formula	C6H8O2
Molar mass	112.128 g·mol−1
Density	1.082-1.088 g/mL (20 °C)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P317, P330, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

5-Methylfurfuryl alcohol is an organic compound with the formula C₆H₈O₂. It is one of many volatile compounds present in Nicotiana tabacum,^[3] and is formed from the reduction of 5-methylfurfural,^[4] a compound formed from the reduction of 5-bromo- or 5-chloromethylfurfural.^[5] It is a colorless liquid listed as a food additive with FEMA number 4544 and JECFA number 2099.^[2]

Occurrence

5-Methylfurfuryl alcohol naturally occurs as one of many volatile compounds present in Nicotiana tabacum, or cultivated tobacco. The compound appears at much lower concentration in tobacco leaves than the more common aldehyde furfural.^[3]

As the reduction product of 5-methylfurfural, 5-methylfurfuryl alcohol occurs in barrel-aged wines along with 5-methylfurfuryl ethyl ether.^[4]

Synthesis

5-Methylfurfuryl alcohol can be produced through a reduction of 5-methylfurfural with lithium aluminium hydride,^[4] though historically the reduction has been performed starting with methyl 5-methyl–2-furoate rather than 5-methylfurfural.^[6]

References

^ "2-Furanmethanol, 5-methyl-". NIST Chemistry WebBook, SRD 69. 2023.
^ ^a ^b ^c "Online Edition: "Specifications for Flavourings"". Food and Agriculture Organization of the United Nations. 2012. Retrieved June 25, 2024.
^ ^a ^b Peng, Fumin; Sheng, Liangquan; Liu, Baizhan; Tong, Hongwu; Liu, Shaomin (June 2004). "Comparison of different extraction methods: steam distillation, simultaneous distillation and extraction and headspace co-distillation, used for the analysis of the volatile components in aged flue-cured tobacco leaves". Journal of Chromatography A. 1040 (1): 1–17. doi:10.1016/j.chroma.2004.03.057. PMID 15248421.
^ ^a ^b ^c 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.
^ "5-Methylfurfural". Organic Syntheses. 14: 62. 1934. doi:10.15227/orgsyn.014.0062.
^ Mndzhoian, A. L. (1959), Mndzhoian, A. L. (ed.), "5-Methylfurfuryl Alcohol", Syntheses of Heterocyclic Compounds, Boston, MA: Springer US, pp. 108–110, doi:10.1007/978-1-4757-6658-5_47, ISBN 978-1-4757-6660-8, retrieved 2024-07-25

[NISTWebbook-1] "2-Furanmethanol, 5-methyl-". NIST Chemistry WebBook, SRD 69. 2023.

[FAO-2] "Online Edition: "Specifications for Flavourings"". Food and Agriculture Organization of the United Nations. 2012. Retrieved June 25, 2024.

[:0-3] Peng, Fumin; Sheng, Liangquan; Liu, Baizhan; Tong, Hongwu; Liu, Shaomin (June 2004). "Comparison of different extraction methods: steam distillation, simultaneous distillation and extraction and headspace co-distillation, used for the analysis of the volatile components in aged flue-cured tobacco leaves". Journal of Chromatography A. 1040 (1): 1–17. doi:10.1016/j.chroma.2004.03.057. PMID 15248421.

[:1-4] 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.

[5] "5-Methylfurfural". Organic Syntheses. 14: 62. 1934. doi:10.15227/orgsyn.014.0062.

[6] Mndzhoian, A. L. (1959), Mndzhoian, A. L. (ed.), "5-Methylfurfuryl Alcohol", Syntheses of Heterocyclic Compounds, Boston, MA: Springer US, pp. 108–110, doi:10.1007/978-1-4757-6658-5_47, ISBN 978-1-4757-6660-8, retrieved 2024-07-25

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