Methyl isoeugenol

Methyl isoeugenol
Names
	Preferred IUPAC name 1,2-dimethoxy-4-[(E)-prop-1-enyl]benzene
	Other names Isomethyleugenol; Methylisoeugenol; 4-Propenylveratrole
Identifiers
CAS Number	6379-72-2 (E) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:6877;
ChemSpider	553362;
ECHA InfoCard	100.002.023
KEGG	C10478;
PubChem CID	637776;
UNII	J6M6C71VVR (E) ;
CompTox Dashboard (EPA)	DTXSID0052621 ;
	InChI InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4-8H,1-3H3/b5-4+;
	SMILES CC=CC1=CC(OC)=C(OC)C=C1;
Properties
Chemical formula	C11H14O2
Molar mass	178.231 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methyl isoeugenol (isomethyleugenol) is a phenylpropanoid, the methyl ether of isoeugenol, found in certain essential oils.^[1]^[2] It can occur as both (E)- and (Z)-isomers.

Biosynthesis

In the wildflower Clarkia breweri, methyl isoeugenol is produced from isoeugenol by the enzyme (Iso)eugenol O-methyltransferase. This uses the cofactor, S-Adenosyl methionine (SAM) to provide the methyl group.^[3]^[4]

isoeugenol

+ SAM

methyl isoeugenol

+ SAH

References

↑ Purchase, R.; Ford, G. P.; Creasy, D. M.; Brantom, P. G.; Gangolli, S. D. (1992-06-01). "A 28-day feeding study with methyl isoeugenol in rats". Food and Chemical Toxicology. 30 (6): 475–481. doi:10.1016/0278-6915(92)90098-6. ISSN 0278-6915.
↑ Raguso, Robert A.; Schlumpberger, Boris O.; Kaczorowski, Rainee L.; Holtsford, Timothy P. (2006). "Phylogenetic fragrance patterns in Nicotiana sections Alatae and Suaveolentes". Phytochemistry. 67 (17): 1931–1942. doi:10.1016/J.PHYTOCHEM.2006.05.038. PMID 16843507.
↑ Wang J, Pichersky E (1998). "Characterization of S-adenosyl-L-methionine:(iso)eugenol O-methyltransferase involved in floral scent production in Clarkia breweri". Arch. Biochem. Biophys. 349 (1): 153–60. doi:10.1006/abbi.1997.0452. PMID 9439593.
↑ JP, Pichersky E; Lavid, N; Zubieta, C; Chen, F; Beuerle, T; Lewinsohn, E; Noel, JP; Pichersky, E (2002). "Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family". Plant Cell. 14 (2): 505–19. doi:10.1105/tpc.010327. PMC 152928. PMID 11884690.

[1] Purchase, R.; Ford, G. P.; Creasy, D. M.; Brantom, P. G.; Gangolli, S. D. (1992-06-01). "A 28-day feeding study with methyl isoeugenol in rats". Food and Chemical Toxicology. 30 (6): 475–481. doi:10.1016/0278-6915(92)90098-6. ISSN 0278-6915.

[2] Raguso, Robert A.; Schlumpberger, Boris O.; Kaczorowski, Rainee L.; Holtsford, Timothy P. (2006). "Phylogenetic fragrance patterns in Nicotiana sections Alatae and Suaveolentes". Phytochemistry. 67 (17): 1931–1942. doi:10.1016/J.PHYTOCHEM.2006.05.038. PMID 16843507.

[3] Wang J, Pichersky E (1998). "Characterization of S-adenosyl-L-methionine:(iso)eugenol O-methyltransferase involved in floral scent production in Clarkia breweri". Arch. Biochem. Biophys. 349 (1): 153–60. doi:10.1006/abbi.1997.0452. PMID 9439593.

[4] JP, Pichersky E; Lavid, N; Zubieta, C; Chen, F; Beuerle, T; Lewinsohn, E; Noel, JP; Pichersky, E (2002). "Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family". Plant Cell. 14 (2): 505–19. doi:10.1105/tpc.010327. PMC 152928. PMID 11884690.

[1]

[2]

[3]

[4]

Biosynthesis

See also

References