3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||296.539 g·mol−1|
|Appearance||Colorless viscous liquid|
|Density||0.8458 g/cm3 (20 ºC)|
|Boiling point||334.88 °C (634.78 °F; 608.03 K)|
|Solubility in other solvents||Very soluble in benzene, diethyl ether, and ethanol|
|P264, P273, P280, P302+P352, P321, P332+P313, P362, P391, P501|
|Flash point||135 °C (275 °F; 408 K) (closed cup)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
It can be synthesized in six steps from pseudoionone and propargyl alcohol. Total synthesis begins with the combination of acetylene and acetone to produce 3-methyl-1-butyn-3-ol. Hydrogenation by palladium catalysis results in 3-methyl-1-buten-3-ol. Reaction with diketene or acetic acid ester creates the acetoacetate; thermal reaction leads to 2-methyl-2-hepten-6-one. The steps of adding acetylene and then isopropenyl methyl ether and hydrogenating the product are done twice (this involves an intermediate of pseudoionone); then acetylene is added to create dehydroisophytol. Hydrogenation results in isophytol.
Production industrially was estimated to be 35000 to 40000 tons in 2002, created by total synthesis, with about 99.9% used in synthesizing vitamin E and vitamin K1. More than 95% of the less than 40 tons used annually in consumer products is as a fragrance. Less than 2 tons a year is used for flavoring.
In perfumes the concentration is 0.2% v/v at most.
- McGinty, D.; Letizia, C.S.; Api, A.M. (January 2010). "Fragrance material review on isophytol". Food and Chemical Toxicology. 48: S76–S81. doi:10.1016/j.fct.2009.11.015. ISSN 0278-6915. PMID 20141882.
- OECD 2003, p. 6.
- OECD 2003, p. 7.
- Sato, Kikumasa; Kurihara, Yoshie; Abe, Shigehiro (January 1963). "Synthesis of Isophytol". The Journal of Organic Chemistry. 28 (1): 45–47. doi:10.1021/jo01036a009.
- OECD 2003, p. 45.
- OECD 2003, p. 22.
- OECD 2003, p. 12.
- OECD 2003, p. 3.
- OECD (21 February 2003). Isophytol SIDS Initial Assessment Report for SIAM 16 (PDF) (Report). UNEP. Archived from the original (PDF) on 28 March 2012. Retrieved 27 January 2020.