Adipostatin A

Adipostatin A is an alkylresorcinol, a type of phenolic lipids composed of long aliphatic chains and phenolic rings. Chemically, it is similar in structure to urushiol, the irritant found in poison ivy.

Adipostatin A

Names
Preferred IUPAC name 5-Pentadecylbenzene-1,3-diol
Other names Cardol 5-n- pentadecylcatechol Pentadecylresorcinol 5-Pentadecylresorcinol
Identifiers
CAS Number	3158-56-3 Y
3D model (JSmol)	Interactive image
ChemSpider	69081
ECHA InfoCard	100.019.636
PubChem CID	76617
UNII	U1FU33YCG0 Y
CompTox Dashboard (EPA)	DTXSID7062875
InChI InChI=1S/C21H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-20(22)18-21(23)17-19/h16-18,22-23H,2-15H2,1H3 Key: KVVSCMOUFCNCGX-UHFFFAOYSA-N InChI=1/C21H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-20(22)18-21(23)17-19/h16-18,22-23H,2-15H2,1H3 Key: KVVSCMOUFCNCGX-UHFFFAOYAU
SMILES CCCCCCCCCCCCCCCC1=CC(=CC(=C1)O)O
Properties
Chemical formula	C21H36O2
Molar mass	320.517 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

Adipostatin A can be found in Ginkgo biloba fruits as well as in Streptomyces cyaneus.^[1] It is also found in cashew nutshell liquid (Anacardium occidentale), in Anacardium othonianum and in Ardisia elliptica.^[2]

It is an inhibitor of glycerol-3-phosphate dehydrogenase.^[3]

References

1. Tanaka, A; Arai, Y; Kim, SN; Ham, J; Usuki, T (2011). "Synthesis and biological evaluation of bilobol and adipostatin A". Journal of Asian Natural Products Research. 13 (4): 290–6. doi:10.1080/10286020.2011.554828. PMID 21462031. S2CID 25305504.
2. Koh Hwee Ling, Chua Tung Kian, and Tan Chay Hoon. "A Guide to Medicinal Plants: An Illustrated, Scientific and Medicinal Approach", p. 14. World Scientific Publishing 2009, ISBN 981-283-709-4. Preview available at Google Books
3. Tsuge, N; Mizokami, M; Imai, S; Shimazu, A; Seto, H (1992). "Adipostatins a and B, new inhibitors of glycerol-3-phosphate dehydrogenase". The Journal of Antibiotics. 45 (6): 886–91. doi:10.7164/antibiotics.45.886. PMID 1500355.