Umbilicaric acid

Umbilicaric acid is an organic polyphenolic carboxylic acid made by several species of lichen. It is named after Umbilicaria.[1] Umbilicaric acid is a tridepside, containing three phenol rings.[2]

Umbilicaric acid

Names
IUPAC name 2-Hydroxy-4-[2-hydroxy-4-(4-hydroxy-2-methoxy-6-methylbenzoyl)oxy-6-methylbenzoyl]oxy-6-methylbenzoic acid
Identifiers
CAS Number	30666-92-3
3D model (JSmol)	Interactive image
PubChem CID	12444590
InChI InChI=1S/C25H22O10/c1-11-5-14(26)8-19(33-4)22(11)25(32)35-16-7-13(3)21(18(28)10-16)24(31)34-15-6-12(2)20(23(29)30)17(27)9-15/h5-10,26-28H,1-4H3,(H,29,30) Key: RLRCNRNYRSKNOO-UHFFFAOYSA-N
SMILES CC1=CC(=CC(=C1C(=O)OC2=CC(=C(C(=C2)C)C(=O)OC3=CC(=C(C(=C3)C)C(=O)O)O)O)OC)O
Properties
Chemical formula	C25H22O10
Molar mass	482.441 g·mol^−1
Melting point	203 °C (397 °F; 476 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Identification of unbilicaric acid can be important in the identification of lichen species.[2]

See also

• Gyrophoric acid

References

1. Posner, B.; Feige, G. B. (1992). "Studies on the chemistry of the lichen genus Umbilicaria Hoffm". Zeitschrift für Naturforschung C. 47 (1–2): 1–9. doi:10.1515/znc-1992-1-202.
2. Narui, Takao; Sawada, Keiko; Takatsuki, Satoshi; Okuyama, Toru; Culberson, Chicita F.; Culberson, William Louis; Shibata, Shoji (July 1998). "NMR assignments of depsides and tridepsides of the lichen family Umbilicariaceae". Phytochemistry. 48 (5): 815–822. doi:10.1016/S0031-9422(97)00958-8.