Geranyl formate

Geranyl formate
Names
IUPAC name
Geranyl formate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.037 Edit this at Wikidata
EC Number
  • 203-339-4
KEGG
UNII
  • InChI=1S/C11H18O2/c1-10(2)5-4-6-11(3)7-8-13-9-12/h5,7,9H,4,6,8H2,1-3H3/b11-7+
    Key: FQMZVFJYMPNUCT-YRNVUSSQSA-N
  • CC(=CCC/C(=C/COC=O)/C)C
Properties
C11H18O2
Molar mass 182.263 g·mol−1
Appearance colorless to pale yellow
Density 0.906-0.920 g/cm3
Boiling point 216 °C (421 °F; 489 K)
insoluble
Solubility soluble in alcohol, most fixed oils
insoluble in glycerol, propylene glycol
1.457-1.466
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H317
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Geranyl formate is an organic compound from the group of terpenoid esters, derived from geraniol and formic acid.

Presence

Geranyl formate is found in geranium oil from Pelargonium graveolens. The proportion varies depending on the source; in one study, the content in the essential oil ranged from less than 1% to almost 9%, with an average of about 5%. In another study, the content was between 4.1% and 4.7%. In a third study, the composition of geranium oil was determined depending on the harvest time. In this case, the proportion of geranyl formate varied between 3.8% and 6.2%. It is also found in annatto seeds and is also produced during the autoxidation of geraniol.

Usage

Geranyl formate is approved in the European Union under FL number [de] 09.076 as a general food flavoring. Geranyl formate is also used as a fragrance. As of 2024, the worldwide usage in this area is in the range of 10 to 100 tonnes per year.

References

  1. 1 2 "Geranyl formate". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-10-20.
  2. ↑ Sandasi, M.; Kamatou, G.P.P.; Gavaghan, C.; Baranska, M.; Viljoen, A.M. (2011). "A quality control method for geranium oil based on vibrational spectroscopy and chemometric data analysis". Vibrational Spectroscopy. 57 (2): 242–247. Bibcode:2011VibSp..57..242S. doi:10.1016/j.vibspec.2011.08.002.
  3. ↑ Rajeswara Rao, B.; Kaul, P. N.; Syamasundar, K. V.; Ramesh, S. (2002). "Water soluble fractions of rose-scented geranium (Pelargonium species) essential oil". Bioresource Technology. 84 (3): 243–246. Bibcode:2002BiTec..84..243R. doi:10.1016/S0960-8524(02)00057-3. PMID 12118700.
  4. ↑ Verma, Ram S.; Rahman, Laiq ur; Verma, Rajesh K.; Chauhan, Amit; Singh, Anand (2013). "Essential oil composition of Pelargonium graveolens l'Her ex Ait. Cultivars harvested in different seasons". Journal of Essential Oil Research. 25 (5): 372–379. doi:10.1080/10412905.2013.782476.
  5. ↑ Jondiko, Isaac J.O.; Pattenden, Gerald (1989). "Terpenoids and an apocarotenoid from seeds of Bixa orellana". Phytochemistry. 28 (11): 3159–3162. Bibcode:1989PChem..28.3159J. doi:10.1016/0031-9422(89)80298-5.
  6. ↑ Bäcktorp, Carina; Hagvall, Lina; Börje, Anna; Karlberg, Ann-Therese; Norrby, Per-Ola; Nyman, Gunnar (2008). "Mechanism of Air Oxidation of the Fragrance Terpene Geraniol". Journal of Chemical Theory and Computation. 4 (1): 101–106. Bibcode:2008JCTC....4..101B. doi:10.1021/ct7001495. PMID 26619983.
  7. ↑ "Food and Feed Information Portal Database | FIP".
  8. ↑ Api, A.M.; et al. (2024). "RIFM fragrance ingredient safety assessment, geranyl formate, CAS Registry Number 105-86-2". Food and Chemical Toxicology. 183 114250. doi:10.1016/j.fct.2023.114250. PMID 38040244.