Bilobol

Bilobol
Names

IUPAC name 5-[(Z)-pentadec-8-enyl]benzene-1,3-diol
Other names 5-[(Z)-pentadec-8-enylo]resorcinol 5-pentadecenylresorcinol
Identifiers
ChemSpider	4445147
InChI InChI=1S/C21H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-20(22)18-21(23)17-19/h7-8,16-18,22-23H,2-6,9-15H2,1H3/b8-7- Key: TUGAUFMQYWZJAB-FPLPWBNLSA-N InChI=1/C21H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-20(22)18-21(23)17-19/h7-8,16-18,22-23H,2-6,9-15H2,1H3/b8-7- Key: TUGAUFMQYWZJAB-FPLPWBNLBC
Jmol-3D images	Image Image
PubChem	5281852
SMILES Oc1cc(cc(O)c1)CCCCCCC\C=C/CCCCCC CCCCCCC=CCCCCCCCC1=CC(=CC(=C1)O)O
Properties
Chemical formula	C₂₁H₃₄O₂
Molar mass	318.49 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Bilobol is an alkylresorcinol, a type of phenolic lipids composed of long aliphatic chains and phenolic rings. It is a strong skin irritant related to urushiol and literature suggests that significant cross-sensitivity exists between these compounds.^[1]

Natural occurrences

Bilobol can be found in Gingko biloba fruits.^[2]

References

↑ Matsumoto, Kazuyuki; Fujimoto, Masao; Ito, Kazuo; Tanaka, Hitoshi; Hirono, Iwao (1990). "Comparison of the effects of bilobol and 12-O-tetradecanoylphorbol-13-acetate on skin, and test of tumor promoting potential of bilobol in CD-1 mice". The Journal of Toxicological Sciences 15 (1): 39–46. doi:10.2131/jts.15.39. PMID 2110595.
↑ 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.