Caperatic acid

Caperatic acid
	Structure of caperatic acid
Names
	IUPAC name 2-hydroxy-2-(2-methoxy-2-oxoethyl)-3-tetradecylbutanedioic acid
	Preferred IUPAC name Caperatic acid
	Systematic IUPAC name 2-Hydroxy-1,2,3-heptadecanetricarboxylic acid monomethyl ester
	Other names 5-Methyl hydrogen 3-C-carboxy-2,4-dideoxy-2-tetradecylpentarate; 2-Hydroxy-1,2,3-heptadecanetricarboxylic acid 1-methyl ester;
Identifiers
CAS Number	29227-64-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:144132;
ChEMBL	ChEMBL1553256;
PubChem CID	193112;
	InChI InChI=1S/C21H38O7/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-17(19(23)24)21(27,20(25)26)16-18(22)28-2/h17,27H,3-16H2,1-2H3,(H,23,24)(H,25,26) Key: HMJJWFFZRCLIDN-UHFFFAOYSA-N;
	SMILES CCCCCCCCCCCCCCC(C(=O)O)C(CC(=O)OC)(C(=O)O)O;
Properties
Chemical formula	C21H38O7
Molar mass	402.528 g·mol−1
Melting point	132–133.5 °C (269.6–272.3 °F; 405.1–406.6 K)
Boiling point	549.3 °C (1,020.7 °F; 822.4 K) (predicted)
Solubility in water	1.017 mg/L (predicted)
log P	5.7
Structure
Molecular shape	Flexible chain with carboxyl groups
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	No significant hazards identified
Flash point	180 °C (estimated)
Related compounds
Related compounds	Other lichen-derived depsides and acids
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Caperatic acid is a naturally occurring organic compound classified as a microbial metabolite. The compound has been reported in certain actinobacteria through fermentation and has also been identified in lichens.^[1]

Properties

Caperatic acid is a crystalline organic compound. Computational models predict a boiling point of 549.3 ± 50 °C, but the compound is expected to decompose before reaching this temperature under laboratory conditions. The predicted density is 1.10 g/cm³. ^[2]

Occurrence

Scientists have identified caperatic acid in lichens, particularly Platismatia glauca, which grows across Europe and North America.^[3]

References

^ "Caperatic acid (CHEBI:144132)". ChEBI. EMBL-EBI. Retrieved 21 May 2026.
^ "Caperatic acid". ChemSpider. Retrieved 22 May 2026.
^ Ren, M.; Jiang, S.J.S.; Wang, Y.; Pan, X.P.; Pan, F.F.; Wei, X. (2023). "Discovery and excavation of lichen bioactive natural products". Frontiers in Microbiology. 14 1177123: 112345. doi:10.3389/fmicb.2023.1177123. PMC 10149937. PMID 37138611.

[ChEBI-1] "Caperatic acid (CHEBI:144132)". ChEBI. EMBL-EBI. Retrieved 21 May 2026.

[ChemSpider-2] "Caperatic acid". ChemSpider. Retrieved 22 May 2026.

[Ren2023-3] Ren, M.; Jiang, S.J.S.; Wang, Y.; Pan, X.P.; Pan, F.F.; Wei, X. (2023). "Discovery and excavation of lichen bioactive natural products". Frontiers in Microbiology. 14 1177123: 112345. doi:10.3389/fmicb.2023.1177123. PMC 10149937. PMID 37138611.

[1]

[2]

[3]