Olibanic acid

Olibanic acid is an organic compound that is naturally found in frankincense. Even though it is present in smaller concentrations than other components, it has a highly potent odor and is believed to be one of the key components responsible for the distinctive smell of frankincense. Both the (1S,2S)-(+)-trans and (1S,2R)-(+)-cis enantiomers are present and have similar but not identical "old church"-like odors.[1]

Olibanic acid
Names
IUPAC name
2-octylcyclopropane-1-carboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C12H22O2/c1-2-3-4-5-6-7-8-10-9-11(10)12(13)14/h10-11H,2-9H2,1H3,(H,13,14)
    Key: FLZRNGWKTVAXBN-UHFFFAOYSA-N
  • (+)-trans: InChI=1S/C12H22O2/c1-2-3-4-5-6-7-8-10-9-11(10)12(13)14/h10-11H,2-9H2,1H3,(H,13,14)/t10-,11-/m0/s1
    Key: FLZRNGWKTVAXBN-QWRGUYRKSA-N
  • (−)-trans: InChI=1S/C12H22O2/c1-2-3-4-5-6-7-8-10-9-11(10)12(13)14/h10-11H,2-9H2,1H3,(H,13,14)/t10-,11-/m1/s1
    Key: FLZRNGWKTVAXBN-GHMZBOCLSA-N
  • (+)-cis: InChI=1S/C12H22O2/c1-2-3-4-5-6-7-8-10-9-11(10)12(13)14/h10-11H,2-9H2,1H3,(H,13,14)/t10-,11+/m1/s1
    Key: FLZRNGWKTVAXBN-MNOVXSKESA-N
  • (−)-cis: InChI=1S/C12H22O2/c1-2-3-4-5-6-7-8-10-9-11(10)12(13)14/h10-11H,2-9H2,1H3,(H,13,14)/t10-,11+/m0/s1
    Key: FLZRNGWKTVAXBN-WDEREUQCSA-N
  • CCCCCCCCC1CC1C(=O)O
  • (+)-trans: CCCCCCCC[C@H]1C[C@@H]1C(=O)O
  • (−)-trans: CCCCCCCC[C@@H]1C[C@H]1C(=O)O
  • (+)-cis: CCCCCCCC[C@@H]1C[C@@H]1C(=O)O
  • (−)-cis: CCCCCCCC[C@H]1C[C@H]1C(=O)O
Properties
C12H22O2
Molar mass 198.306 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References

  1. Cerutti-Delasalle C, Mehiri M, Cagliero C, Rubiolo P, Bicchi C, Meierhenrich UJ, Baldovini N (October 2016). "The (+)-cis- and (+)-trans-Olibanic Acids: Key Odorants of Frankincense". Angewandte Chemie International Edition in English. 55 (44): 13719–13723. doi:10.1002/anie.201605242. hdl:2318/1609095. PMID 27699963.


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