Caperatic acid

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.

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

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.

Occurrence

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

References