Olibanic acid

Olibanic acid
Names
	IUPAC name 2-octylcyclopropane-1-carboxylic acid
Identifiers
CAS Number	15898-87-0 ;
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

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]

References

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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[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.