Isophytol is a terpenoid alcohol that is used as a fragrance and as an intermediate in the production of vitamin E and K1.[1][2]
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| Names | |
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| IUPAC name
3,7,11,15-Tetramethylhexadec-1-en-3-ol
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| Identifiers | |
3D model (JSmol)
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| ECHA InfoCard | 100.007.281 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C20H40O | |
| Molar mass | 296.539 g·mol−1 |
| Appearance | Colorless viscous liquid |
| Density | 0.8458 g/cm3 (20 °C) |
| Boiling point | 334.88 °C (634.78 °F; 608.03 K) |
| Poor | |
| Solubility in other solvents | Very soluble in benzene, diethyl ether, and ethanol |
| Hazards | |
| GHS labelling: | |
 
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| 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).
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Occurrence
editIsophytol has been in found in two red algae species and more than 15 plant species. Concentrations found have been low.[3]
Synthesis
editIt can be synthesized in six steps from pseudoionone and propargyl alcohol.[4] 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.[3]
Uses
editProduction industrially was estimated to be 35000 to 40000 tons in 2002,[5] 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.[6]
In perfumes the concentration is 0.2% v/v at most.[7]
Toxicology
editSee also
editReferences
edit- ^ 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.
- ^ a b 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.
Bibliography
edit- 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.