Isoeugenol

Isoeugenol^[1]
Names
	IUPAC name 2-Methoxy-4-[(E)-prop-1-enyl]phenol
	Other names 4-Hydroxy-3-methoxy-1-propenylbenzene; 2-Methoxy-4-propenylphenol; 4-Propenylguaiacol
Identifiers
CAS Number	97-54-1;
3D model (JSmol)	(trans): Interactive image;
ChEBI	CHEBI:18224;
ChEMBL	ChEMBL445206;
ChemSpider	21106129 (trans);
ECHA InfoCard	100.002.356
EC Number	202-590-7;
KEGG	C10469;
PubChem CID	7338;
UNII	5M0MWY797U;
CompTox Dashboard (EPA)	DTXSID7022413 ;
	InChI InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+; (trans): InChI=1/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+ Key: BJIOGJUNALELMI-ONEGZZNKBO;
	SMILES (trans): C/C=C/C1=CC(=C(C=C1)O)OC;
Properties
Chemical formula	C10H12O2
Molar mass	164.204 g·mol−1
Appearance	Oily liquid
Density	1.080
Melting point	−10 °C (14 °F; 263 K)
Boiling point	266 °C (511 °F; 539 K)
Solubility in water	810 mg/L
Solubility	Soluble in most organic solvents
Vapor pressure	0.0135 mmHg
Pharmacology
ATCvet code	QN01AX94 (WHO)
Legal status	CA: ℞-only;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Isoeugenol is a propenyl-substituted guaiacol. A phenylpropanoid, it occurs in the essential oils of plants such as ylang-ylang (Cananga odorata), and is a component of wood smoke and liquid smoke. It can be synthesized from eugenol and has been used in the manufacture of vanillin. It may occur as either the cis (Z) or trans (E) isomer. Trans (E) isoeugenol is crystalline while cis (Z) isoeugenol is a liquid.^[6] Isoeugenol is one of several phenolic compounds responsible for the mold-inhibiting effect of smoke on meats and cheeses.^[7]

Allergy

Some individuals experience a hives-like reaction to long-term exposure to Isoeugenol, which is named as Fragrance in the ingredients of consumer products such as soaps, shampoos and detergents, bath tissue, and topical cosmetic applications. Sensitivity to isoeugenol (Fragrance) may be identified with a clinical patch test.^[8]

References

^ The Merck Index, 12th edition, Merck & Co, Whitehouse Station, New Jersey, USA, 1996.
^ HERA; HERA Risk Assessment of Isoeugenol (Draft). Human and Environmental Risk Assessment on ingredients of Household Cleaning Products. Isoeugenol (CAS 97-54-1). Available from, as of June 23, 2012: http://www.heraproject.com/
^ Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 710
^ NIST; NIST Chemistry WebBook. Phenol, 2-methoxy-4-(1-propenyl)- (97-54-1). NIST Standard Reference Database No. 69, June 2005 Release. Washington, DC: US Sec Commerce. Available from, as of June 25, 2012: http://webbook.nist.gov
^ "Notice: Multiple additions to the Prescription Drug List (PDL) [2023-10-26]". Health Canada. 26 October 2023. Retrieved 3 January 2024.
^ Merck Index
^ WENDORFF, WILLIAM L.; RIHA, WILLIAM E.; MUEHLENKAMP, EMILY (November 1993). "Growth of Molds on Cheese Treated with Heat or Liquid Smoke". Journal of Food Protection. 56 (11): 963–966. doi:10.4315/0362-028X-56.11.963. PMID 31113088.
^ AllergEAZE. "PF137 Isoeugenol" (PDF). AllergEAZE. Retrieved 2015-08-25.^{[permanent dead link]}

[1] The Merck Index, 12th edition, Merck & Co, Whitehouse Station, New Jersey, USA, 1996.

[2] HERA; HERA Risk Assessment of Isoeugenol (Draft). Human and Environmental Risk Assessment on ingredients of Household Cleaning Products. Isoeugenol (CAS 97-54-1). Available from, as of June 23, 2012: http://www.heraproject.com/

[3] Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 710

[4] NIST; NIST Chemistry WebBook. Phenol, 2-methoxy-4-(1-propenyl)- (97-54-1). NIST Standard Reference Database No. 69, June 2005 Release. Washington, DC: US Sec Commerce. Available from, as of June 25, 2012: http://webbook.nist.gov

[5] "Notice: Multiple additions to the Prescription Drug List (PDL) [2023-10-26]". Health Canada. 26 October 2023. Retrieved 3 January 2024.

[6] Merck Index

[7] WENDORFF, WILLIAM L.; RIHA, WILLIAM E.; MUEHLENKAMP, EMILY (November 1993). "Growth of Molds on Cheese Treated with Heat or Liquid Smoke". Journal of Food Protection. 56 (11): 963–966. doi:10.4315/0362-028X-56.11.963. PMID 31113088.

[8] AllergEAZE. "PF137 Isoeugenol" (PDF). AllergEAZE. Retrieved 2015-08-25.^{[permanent dead link]}

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