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Citronellyl acetate

From Wikipedia, the free encyclopedia
Citronellyl acetate
Names
IUPAC name
3,7-dimethyloct-6-enyl acetate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.251 Edit this at Wikidata
EC Number
  • 205-775-0
KEGG
UNII
  • InChI=1S/C12H22O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,11H,5,7-9H2,1-4H3
    Key: JOZKFWLRHCDGJA-UHFFFAOYSA-N
  • CC(CCC=C(C)C)CCOC(=O)C
Properties[1]
C12H22O2
Molar mass 198.306 g·mol−1
Appearance colourless
Odor fruity
Density 0.888 g/cm3
Boiling point 229 °C (444 °F; 502 K)
insoluble
Solubility soluble in alcohol, most fixed oils
insoluble in glycerol, propylene glycol
log P 4.220
1.440-1.450
Hazards
GHS labelling:[1]
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H315, H319, H411
P264, P264+P265, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Citronellyl acetate is a synthetically made and naturally occurring organic compound from the group of carboxylic acid esters. It occurs naturally in citrus fruits, but is also used industrially as a flavoring agent.

Occurrence

[edit]

Citronellyl acetate is found in the peel oils of various citrus fruits, such as oranges, bitter oranges, lemons, and grapefruits.[2][3] It is also an important aroma component in kumquat oil[4] and in roses ( Rosa hybrida ).[5] It is also found in Douglas fir,[6] in Vitex agnus-castus ,[7] in Corymbia citriodora,[8] in certain subspecies of common juniper,[9] in catnip[10] and in Sichuan pepper.[11]

Synthesis

[edit]

Citronellyl acetate can be produced enzymatically, i.e., catalyzed by a lipase, via various routes, for example by direct esterification of acetic acid with citronellol, by transesterification of butyl acetate with citronellol, or by transesterification of citronellyl butyrate [de] with butyl acetate.[12]

Usage

[edit]

Citronellyl acetate is used as a flavoring agent and is generally approved for use in food in the EU under FL number 09.012.[13]

Safety

[edit]

Citronellyl acetate is neither cytotoxic nor genotoxic, but it can cause sensitization. In animal studies with rats and mice, adverse health effects were only observed at higher doses.[14]

References

[edit]
  1. 1 2 PubChem. "Citronellyl Acetate". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-09-26.
  2. ↑ Mans H. Boelens, Rafael Jimenez (1989-01-01), "The Chemical Composition of Some Mediterranean Citrus Oils", Journal of Essential Oil Research, vol. 1, no. 4, pp. 151–159, doi:10.1080/10412905.1989.9697776
  3. ↑ Manuel G. Moshonas (1971-07-01), "Analysis of carbonyl flavor constituents from grapefruit oil", Journal of Agricultural and Food Chemistry, vol. 19, no. 4, pp. 769–770, Bibcode:1971JAFC...19..769M, doi:10.1021/jf60176a019
  4. ↑ Hyang-Sook Choi (2005-03-01), "Characteristic Odor Components of Kumquat (Fortunella japonica Swingle) Peel Oil", Journal of Agricultural and Food Chemistry, vol. 53, no. 5, pp. 1642–1647, Bibcode:2005JAFC...53.1642C, doi:10.1021/jf040324x, PMID 15740053
  5. ↑ Moshe Shalit, Inna Guterman, Hanne Volpin, Einat Bar, Tal Tamari, Naama Menda, Zach Adam, Dani Zamir, Alexander Vainstein, David Weiss, Eran Pichersky, Efraim Lewinsohn (2003-04-01), "Volatile Ester Formation in Roses. Identification of an Acetyl-Coenzyme A. Geraniol/Citronellol Acetyltransferase in Developing Rose Petals", Plant Physiology, vol. 131, no. 4, pp. 1868–1876, doi:10.1104/pp.102.018572, PMC 166943, PMID 12692346{{citation}}: CS1 maint: multiple names: authors list (link)
  6. ↑ Tsutomu. Sakai, Henk. Maarse, Richard E. Kepner, Walter G. Jennings, William M. Longhurst (1967-11-01), "Volatile components of Douglas fir needles", Journal of Agricultural and Food Chemistry, vol. 15, no. 6, pp. 1070–1072, Bibcode:1967JAFC...15.1070S, doi:10.1021/jf60154a027{{citation}}: CS1 maint: multiple names: authors list (link)
  7. ↑ Felice Senatore, Giovanna Della Porta, Ernesto Reverchon (May 1996), "Constituents ofVitex agnus-castus L. Essential Oil", Flavour and Fragrance Journal, vol. 11, no. 3, pp. 179–182, doi:10.1002/(SICI)1099-1026(199605)11:3<179::AID-FFJ566>3.0.CO;2-6{{citation}}: CS1 maint: multiple names: authors list (link)
  8. ↑ Jun Han, Soon-Il Kim, Byeoung-Ryeol Choi, Sang-Guei Lee, Young-Joon Ahn (December 2011), "Fumigant toxicity of lemon eucalyptus oil constituents to acaricide-susceptible and acaricide-resistant Tetranychus urticae", Pest Management Science, vol. 67, no. 12, pp. 1583–1588, Bibcode:2011PMSci..67.1583H, doi:10.1002/ps.2216, PMID 21674753{{citation}}: CS1 maint: multiple names: authors list (link)
  9. ↑ Robert P. Adams, P. S. Beauchamp, Vasu Dev, Radha M. Bathala (January 2010), "The Leaf Essential Oils of Juniperus communis L. Varieties in North America and the NMR and MS Data for Isoabienol", Journal of Essential Oil Research, vol. 22, no. 1, pp. 23–28, doi:10.1080/10412905.2010.9700258{{citation}}: CS1 maint: multiple names: authors list (link)
  10. ↑ Renata Baranauskiene, Rimantas P. Venskutonis, Jan C. R. Demyttenaere (2003-06-01), "Sensory and Instrumental Evaluation of Catnip (Nepeta cataria L .) Aroma", Journal of Agricultural and Food Chemistry, vol. 51, no. 13, pp. 3840–3848, Bibcode:2003JAFC...51.3840B, doi:10.1021/jf021187b, PMID 12797753{{citation}}: CS1 maint: multiple names: authors list (link)
  11. ↑ Tsutomu Sakai, Kazuo Yoshihara, Yoshio Hirose (August 1968), "Constituents of Fruit Oil from Japanese Pepper", Bulletin of the Chemical Society of Japan, vol. 41, no. 8, pp. 1945–1950, doi:10.1246/bcsj.41.1945, PMID 5716810{{citation}}: CS1 maint: multiple names: authors list (link)
  12. ↑ H.F. De Castro, P.C. De Oliveira, E.B. Pereira (1997), "Evaluation of different approaches for lipase catalysed synthesis of citronellyl acetate", Biotechnology Letters, vol. 19, no. 3, pp. 229–232, doi:10.1023/A:1018349406159{{citation}}: CS1 maint: multiple names: authors list (link)
  13. ↑ "Food and Feed Information Portal Database | FIP". Retrieved 2023-10-21.
  14. ↑ A.M. Api, D. Belsito, D. Botelho, M. Bruze, G.A. Burton, J. Buschmann, M.A. Cancellieri, M.L. Dagli, M. Date, W. Dekant, C. Deodhar, A.D. Fryer, L. Jones, K. Joshi, M. Kumar, A. Lapczynski, M. Lavelle, I. Lee, D.C. Liebler, H. Moustakas, M. Na, T.M. Penning, G. Ritacco, J. Romine, N. Sadekar, T.W. Schultz, D. Selechnik, F. Siddiqi, I.G. Sipes, G. Sullivan, Y. Thakkar, Y. Tokura (January 2022), "RIFM fragrance ingredient safety assessment, citronellyl acetate, CAS Registry Number 150-84-5", Food and Chemical Toxicology, vol. 159, doi:10.1016/j.fct.2021.112710, PMID 34848257{{citation}}: CS1 maint: multiple names: authors list (link)
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