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
CAS Number	15898-87-0^N
3D model (JSmol)	Interactive image (+)-trans: Interactive image (−)-trans: Interactive image (+)-cis: Interactive image (−)-cis: Interactive image
ChemSpider	2501294
PubChem CID	(+)-trans: 1713016 (−)-trans: 1713014 (+)-cis: 1713018 (−)-cis: 1713012
CompTox Dashboard (EPA)	DTXSID60390651
InChI 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
SMILES 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
Chemical formula	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.